best road trips starting in chicago

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide. It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• 57 Coolest Things to Do in Chicago for 2023
• Planning a Road Trip in the USA: 13 Best Routes!
• 11 Unique Stops on the Drive from Chicago to Atlanta
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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The 17 best road trips from Chicago

Need a change of scenery? Load up the car and embark on one of the best road trips from Chicago.

No coast? No problem. Chicago can sometimes feel like a Midwest oasis, but there's plenty to see just a scenic road trip away. With summer quickly approaching, you can spend a few weekends sipping bourbon in Louisville, hiking  in Eau Claire or sunbathing in Door County. So if you're not sure where to start, check out our list of unique nearby destinations , load up the car, turn up "Life is a Highway" and hit the road—one of these routes from Chicago could quickly become your preferred weekend getaway . 

RECOMMENDED: The best day trips from Chicago

Been there, done that? Think again, my friend.

Best road trips from Chicago

1.  st louis, mo.

Driving time from Chicago:  Four and a half hours

While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly so), there's a lot more to discover in the Gateway to the West—like custard from Ted Drewes and a walk around Forest Park. There's also a ton to see on the five-hour drive from Chicago: Stop off in Springfield to see attractions like the Illinois State Capitol, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

2.  Eau Claire, WI

Driving time from Chicago:  Five hours

Folks head to the Chippewa Valley in northern Wisconsin for its rolling hills and colorful foliage (plus plenty of beer and cheese to smuggle back to Chicago), but there are some worthy sights along the road as well. Snap a selfie with Pinkie the Elephant in DeForest, WI and sample cranberry-flavored everything at the Wisconsin Cranberry Discovery Center   in Warrens, WI. Once you're in Eau Claire, trade in the car for a kayak:  Riverside Bike & Skate   in downtown Eau Claire rents canoes and kayaks and has shuttles that will drive you upstream so you can hit the Chippewa River. 

3.  Traverse City, MI

The charming resort town of Traverse City, located at Michigan’s northern tip, offers plenty to do for nature enthusiasts. Clinch Park and Bryant Park have gorgeous, popular beaches while the more remote Haserot and North Bar Lake beaches offer the chance for a secluded getaway. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America, as well photo-ops at the Grand Traverse and Little Sable lighthouses. 

4.  Detroit, MI

Driving time from Chicago:  Four and a half hours

Despite what Blackhawks fans may chant, there is plenty about Detroit that doesn’t suck. You could easily spend a day or two on art alone, thanks to world-class museums like the Detroit Institute of Arts and the Museum of Contemporary Art Detroit ; powerful, immersive public art like the Heidelberg Project and colorful, whimsical folk art like Hamtramck Disneyland . Enjoy a leisurely morning browsing at Eastern Market showcasing dozens of artisan food producers, makers and crafters, and then check out the tempting restaurant and bar options nearby. On the way home, stop in neighboring Dearborn, home to the largest and most diverse Arab community in the U.S., for delicious food at spots like Al-Ameer , Sheeba and Shatila Bakery . 

5.  Galena, IL

Driving time from Chicago : Three hours

At the top of many Chicagoans city escape must-visit list is Galena, Illinois. This charming town just under three hours from the city is known for its history, 19th-century architecture and resorts. There are hundreds of unique and antique shops in the city center to add some vintage pizzazz to your living room. History buffs can head over to the  Ulysses S. Grant Home  to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into  Log Cabin Steakhouse , which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual  Great Galena Balloon Race .

6.  Door County, WI

The road trip doesn't end when you reach Door County; There's plenty to navigate by car as you wander the series of small towns located on a beautiful 75-mile peninsula surrounded by Lake Michigan and Green Bay. There are also 53 public beaches, five state parks, and 300 miles of shoreline so get ready to put some miles on your car. Need a pit stop? Milwaukee is a little less than half way. 

7.  Louisville, KY

Kentucky’s largest city, located just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm. The home of the old fashioned and mint julep embraces its role as the gateway to Bourbon Country. The city now has over 10 tourable distilleries, including   Evan Williams,   Angel’s Envy   and  Old Forester . If bourbon and honkytonk aren't for you, downtown Louisville has an incredible art scene and is booming with independent businesses and charming shops. 

Discover the best things to do in Louisville

8.  Madison, WI

Driving time from Chicago: Three hours

Sure the Midwest loves its college towns, but Madison's proximity to five surrounding lakes make it one of the more of the scenic ones. The abundance of waterways make kayaking, rafting and canoeing especially popular—you can book them directly through Madison Boats . For those averse to using their sea legs, there's the 16-acre Olbrich Botanical Gardens for all ages or the National Mustard Museum (yes, you read that correctly). It wouldn't be a trip to Wisconsin without trying blocks and blocks of cheese, so make sure to stop by the "Capital of Cheese" known as Fromagination in downtown Madison. 

9.  Cincinnati, OH

If Skyline Chili is not your bag, don’t worry—there’s a whole lot more to the Queen City than its most famous tourist foodstuff. Cincy has been undergoing a major glow-up over the past decade or so, from the ever-evolving Smale Riverfront Park, which offers lots to do and gorgeous views of the skyline and the Ohio River to the revitalization of the historic Over-the-Rhine neighborhood. There, you'll find a number of must-visit spots, including the popular Rhinegeist Brewery, the vibrant Findlay Market , the stunning Music Hall and Washington Park , which sports a sweet playground and community events throughout the year. Plus, the Cincinnati Zoo is one of the best in the country, and the only place you can see Internet icon Fiona the Hippo in person. That in itself is worth the trip.

10.  Shawnee Hills Wine Trail, IL

Driving time from Chicago:  Six hours

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 3 5-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features over 10  award-winning wineries in cute towns like Cobden, Alto Pass, and Pomona. If you need more than wine to prompt a trip, there's plenty of nature in the vicinity and the nearby town of Murphysboro is home to some of the finest BBQ in the Midwest at 17th Street Barbecue . 

11.  Bloomington, IN

Driving time from Chicago:  Four hours

This cozy college town offers some big-city amenities, but it's the surrounding hills, forests and lakes that make it special. A short itinerary could look like: Hike the Deam Wilderness trails ; s ee the Morgan-Monroe State Forest wildflowers; admire the Cedar Bluffs Nature Preserve limestone bluffs; g o fishing at the reservoir lakes. Just don't forget to leave room for a meal at  Feast Market & Cellar , a family-owned kitchen with a lovely corner porch where everything is made from scratch daily. 

12.  Saugatuck, MI

Driving time from Chicago:  Two and a half hours

This dreamy lakeside town (and next-door neighbor Douglas) has long been a favorite of Chicagoans looking to spend time on the water, whether it’s a boat on the Kalamazoo River or a relaxing day on one of the area’s six clean, inviting beaches. From hiking the Saugatuck Dunes to window shopping on Butler Street to enjoying dinner and drinks alfresco, there are many ways to get some much-needed fresh air here. It’s also one of the Midwest’s best queer-friendly vacation destinations, home to more than 100 LGBTQ-owned and friendly businesses. 

13.  Ann Arbor, MI

Driving time from Chicago:  Four hours

If you'd rather stick to less-crowded cities, skip Detroit and opt for Ann Arbor instead. Foodies and beer nerds will love this low-key vacation spot for its plethora of good restaurants and breweries. Home to the renowned University of Michigan, this city’s quaint downtown is full of unique shops, spots to eat and so much more (make sure Blank Slate Creamery is on your list). 

14.  Toledo, OH

The road from Chicago to Ohio is filled with worthwhile attractions, including Indiana Dunes State Park and the Hall of Heroes Super Hero Museum in Elkhart, Indiana. Once you arrive in Toledo, you'll be greeted with picturesque churches, wild urban parks, a trendy jazz culture and plenty of microbreweries to keep you busy. Just outside the city you'll also find fall-harvest overload in the way of apple and pumpkin farms where you can pick your own fruits and veggies and gorge on baked treats.

15.  Shipshewana, IN

Driving time from Chicago:  Two hours

OK, just hear us out. The heart of Indiana Amish country is a great option for a convenient road trip perfect for families, history buffs and, most of all, antiquers. The Shipshewana Trading Place Flea Market is a bargain-hunter’s dream—the largest flea market in the Midwest, with lively auctions Wednesday mornings. After a morning of browsing and bargaining, you’ll work up an appetite for some Amish home cooking, which you can even sample in a  literal Amish home . For outdoorsy types, nearby Mongo offers canoe and kayak rentals for a relaxing day on the water. 

16.  Des Moines, IA

Driving time from Chicago: Five hours

There's a surprising amount to explore over a weekend in Des Moines, from more than 20 breweries in the metro area to the six-mile Art Route , which showcases 87 public art pieces from sculptures to murals. But what really makes Des Moines worth visiting are its summer events, like the eclectic 80/35 music festival, and, of course, the festive juggernaut that is the Iowa State Fair , where you can get 69 different food-on-a-stick creations (nice). When you're heading back on I-80, don't miss the World's Largest Truck Stop in Walcott, truly a site to behold.

17.  Columbus, IN

Driving time from Chicago : Three and a half hours

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation. Roughly 70 different constructions sprinkled around the city and county make this city an architectural wonder. Take an  Architectural Highlights Tour  of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Make another pit stop of striking constructions with a stroll through Mill Race Park , an 85-acre riverfront park near the city's center. Once you’ve worked up an appetite, stop by  Columbus Bar , the oldest bar and restaurant in town.

Need more travel inspiration?

The best weekend getaways from chicago for families.

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

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30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

There may be affiliate links in this post, which means we may get a small commission if you make a purchase. It’s at no extra cost to you and helps keep TLT free. Everybody wins!

Road Trips from Chicago

How to choose the best road trips from chicago.

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area, exploreelginarea.com

Indiana Dunes National Park, Indiana

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana, southshorecva.com

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce, harborcountry.org

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin, visitkenosha.com

McHenry County, Illinois

Driving time: 1 hour 30 minutes

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County, visitmchenrycounty.com

Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau, janesvillecvb.com

Lake Geneva, Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva, visitlakegeneva.com

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee, visitmilwaukee.org

Lafayette, Indiana

Driving time: 2 hours

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette, homeofpurdue.com

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana, visitshipshewana.com

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan, visitsheboygan.com

Elkhart Lake, Wisconsin

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena, visitgalena.org

Hendricks County, Indiana

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County, visithendrickscounty.com

More Road Trips from Chicago between 2 and 3 hours

• Madison, Wisconsin; 2 hours 45 minutes
• New Glarus, Wisconsin; 2 hours 45 minutes
• Indianapolis, Indiana; 3 hours
• Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne, visitfortwayne.com

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque, traveldubuque.com

Brown County, Indiana

Driving time: 4 hours

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County, browncounty.com

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands, shoresandislands.com

Driving time: 5 hours, or as long as you’d like!

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

• Iowa City, Iowa; 3 hours 45 minutes
• Door County, Wisconsin ; 3 hours 50 minutes
• Bloomington, Indiana ; 4 hours
• Spencer, Indiana : 4 hours
• Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
• Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

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The Best Road Trips from Chicago with Itineraries

Looking to get out and explore? There are so many unique places to visit that are just a car ride away! From quaint small towns to interesting cities to exciting outdoor adventure and everything in between, here are the best road trips from Chicago.

Afterward, you may also be interested in reading Fun Spring Break Trips from Chicago .

The Best Road Trips from Chicago

Starting with quick weekend getaways, this list is ordered by distance and ends with long road trips from Chicago.

HERITAGE TRAIL, INDIANA

This 90-mile scenic route will take you through northern Indiana's off-the-beaten-path towns where time slows down. The loop rambles through the communities of Goshen, Elkhart, Middlebury, Nappanee, Bristol, Wakarusa, and Shipshewana.

You'll discover winding country roads, talented artists, old-fashioned entertainment, recreational areas, blossoming gardens, and delicious treats.

From mid-May to mid-September, the trail coincides with the colorful Quilt Gardens project. 16 gigantic gardens and 23 painted murals embellish the trail with dazzling flowers in unique designs.

Drive Time: 2 hours to Elkhart Visitor Center

On the Way: University of Notre Dame, The Oliver Mansion, and Bonnie Doon Drive-In.

What to Do: Quilt Gardens, Wellfield Botanical Gardens, RV/MH Hall of Fame & Museum, Pumpkinvine Bike Trail, Ruthmere Mansion, Old Bag Factory, Linton's Enchanted Gardens, Bonneyville Mill County Park, and Menno-Hof.

Where to Eat & Drink: Rise N' Roll, Blue Gate Restaurant & Bakery, Iechyd Da Brewing, Das Dutchman Essenhaus, and Dutch Country Market.

Where to Stay: Excellent Hotel with a Great Location and Free Buffet Breakfast

SOUTH HAVEN, MICHIGAN

If you're looking for a relaxing destination with beach access, good restaurants, and a bike trail, South Haven is it. With its close proximity, southwest Michigan is amongst the top one day road trips from Chicago.

The walkable idyllic small town is right down the street from the Lake Michigan waterfront where you can see some of the best sunsets in the Midwest. There's plenty of opportunities to get out on the water: charter a fishing boat, take a sailing excursion or rent a jet ski.

If you'd like to do more than hit the beach then check out the Kal-Haven Trail, a former railroad route, that runs 33.5 miles from South Haven to Kalamazoo. It's a quiet and easy ride through blueberry fields, tree tunnels, and across a few bridges.

Drive Time: 2 hours, 15 minutes

On the Way: Four Winds Casino

What to Do: Kal-Haven Trail, DeGrandchamp Farms, Michigan Maritime Museum, Friends Good Will Tall Ship, and the Farmers Market.

Where to Eat & Drink: Golden Brown Bakery, Harbor Light Brewery, Chomp Gourmet Hot Dogs, Captain Nemo's, Phoenix Street Cafe, Idler Riverboat, Clementine's, and 12 Corners Vineyards.

Where to Stay: Historic Hotel in the Heart of Town walking distance to the Beach

GALENA, ILLINOIS

Galena is a must-experience destination in the Midwest especially if you live in Illinois. It is one of the unforgettable places to visit near Chicago with rolling hills, historic landmarks, and a super charming Main Street that will make you feel like you stepped into a Hallmark movie.

Start your visit at the historic Old Market House built in 1845 and now serves as Galena's Welcome Center. You'll learn about the fascinating history of the area and find information for your visit.

From springtime through fall, bike the River Trail, hike at Casper Bluff Preserve, or paddle the Galena River. The Alpine Slide, a 2,050-foot outdoor track, is a unique 2-minute adventure on the banks of the Mississippi River.

When the snow starts to fall, hit the slopes at Chestnut Mountain, one of the most popular ski destinations in the Midwest, or ice skate, sled or snowshoe at The Nordic Center at Eagle Ridge Resort.

While in town, hop on a trolley for a tour, visit wineries, and browse all the specialty and boutique shops.

Galena is on the Great River Road in Illinois along with some other special stops that make the scenic byway a unique Midwest road trip. Click on the link to read all about it!

Drive Time: 2 hours, 45 minutes

On the Way: Rafters Restaurant, Apple River Fort State Historic Site, Highway 20 Brewing Company, Horseshoe Mound Preserve, and Long Hollow Scenic Overlook.

What to Do: Galena Cellars Vineyard, Ulysses S. Grant Home, Galena Trolley Tour, and Grant Park

Where to Eat & Drink: Frank O'Dowd's Irish Pub & Grill, Durty Gurt's, The Log Cabin Steakhouse, Fried Green Tomatoes, Otto's Place, and Gobby's Sports Pub & Eatery.

Where to Stay: Cozy Hotel with an Indoor Pool & Spa and Cool Bar

PARKE COUNTY, INDIANA

Indiana has 98 historic covered bridges and Parke County is home to 31 of them. The central west area is also home to Indiana's largest festival, The Parke County Covered Bridge Festival, held every October in honor of the famous crossings.

Here, you'll also find quaint towns among rolling hills and two state parks to hike with deep gorges, wooden ladders, rocky hollows, and natural arches making the area one of the best fall road trips from Chicago.

Drive Time: 3 hours

On the Way: Kankakee Sands Bison Viewing

What to Do: Bridgeton Mill, Turkey Run State Park, Mansfield Roller Mill and Covered Bridge, Narrows Covered Bridge, Rockville Lake Park, Roseville Covered Bridge and downtown Rockville.

Where to Eat & Drink: Wheel House Donuts, Cross at Walk Winery, Thirty-Six Saloon, Big Berry, and Drunk Tank Winery.

Where to Stay: Cabin or Hotel Stay with an Indoor Pool

HAMILTON COUNTY, INDIANA

Under 200 miles away from Chicago and just 23 miles north of Indianapolis, Hamilton County is a fantastic option for a weekend getaway.

With lively communities bursting with arts and entertainment districts, outdoor activities, historic squares, boutique shopping, and diverse restaurants, Hamilton County deserves its own place on the list.

If you like to eat and drink, you can dedicate an entire weekend chasing giant pork tenderloins, local donut shops, and/or craft breweries. Make sure to spread your time evenly within the cities of Westfield, Carmel, Noblesville, and Fishers.

On the Way: Fair Oaks Farm, Cairo Skywatch Tower, Wildcreek Winery, and Jerry E. Botanic Gardens.

What to Do: Monon Bike Trail, Carmel Arts and Design District, Strawtown Koteewi Park, Hamilton County Courthouse & Old Sheriff's Residence and County Jail, Center of the Performing Arts,

Where to Eat & Drink: Urban Vines Winery and Brewery, Wolfies Grill, Rosie's Place, Cafe Patachou, Books & Brews, and Divvy Restaurant.

Where to Stay: Upscale Boutique Hotel in a Great Location

INDIANAPOLIS, INDIANA

Home to the state capitol, the world's oldest continuously operated racecourse, and the world's largest children's museum, Indianapolis has endless vacation potential.

Kick off your visit at Monument Circle, an impressive centerpiece circling the 284- foot tall Soldiers' and Sailors' Monument. The spectacular views from the observation deck will get you pumped to explore the city.

Once back on the ground, don't miss The Indianapolis Motor Speedway Museum, home of the Indy 500, for a chance to learn all about the history of racing, fast cars, and to see the track up close and personal.

For those looking for outdoor adventure, the Central Canal and White River State Park offer quiet respites from the bustling urban atmosphere with biking, pedal boat rentals, kayaking and segway tours.

If traveling with kids, spend an entire day at the gigantic Children's Museum of Indianapolis. Each exhibit will entertain the whole family.

What to Do: Indianapolis Motor Speedway, The Children's Museum, Monument Circle, Connor Prairie Interactive History Park, Canal Walk, Indiana State House, White River State Park, and Indianapolis Zoo.

Where to Eat & Drink: St. Joseph Brewery, Cafe Patachou, BRU Burger Bar, The Rathskeller, St. Elmo Steak House, and Slippery Noodle Inn.

Where to Stay: Hotel with Ideal Downtown Location & Indoor Swimming Pool

LAKE ERIE OHIO COASTAL TRAIL & CEDAR POINT

It's time to ditch Lake Michigan and discover another one of the Great Lakes. You can pick up the Lake Erie Ohio Coastal Trail in Toledo and follow the shoreline to Conneaut.

Along the 293-mile route, you'll discover the second-oldest operating amusement park in the United States (which happens to also be the best in the Midwest), old-time lighthouses, water parks an underrated cool city, swimming beaches, coastal towns, and beautiful state parks.

Being along the lake, there are numerous outdoor activities to choose from, plus historical and entertaining options on the drive. You'll have a newfound love and appreciation for Lake Erie after this sensational road trip.

Drive Time: 4 Hours to Toledo

On the Way: University of Notre Dame, Shipshewana, RV/MH Hall of Fame & Museum

What to Do: Marblehead Lighthouse State Park, Cedar Point Amusement Park, Rock n' Roll Hall of Fame, and Fairport Harbor Marine Museum and Lighthouse.

Where to Eat & Drink: Dock's Beach House Restaurant in Port Clinton, New Sandusky Fish Company, Mary's Kitchen in Geneva-on-the-Lake, Old Prague in Vermilion, Madsen Donuts in Geneva, and White Turkey Drive-in.

Where to Stay: Waterfront Property near Cedar Point

BLOOMINGTON, INDIANA

Bloomington tops the list of coolest college towns in the Midwest. There's always something going on between outdoor festivals, sports games, and music events.

Take a tour of one of the most beautiful campuses in the nation, go brewery hopping, or explore the area's natural beauty.

There's a reason Bloomington is referred to as the "Gateway to Scenic Southern Indiana," just twenty minutes away is the beautiful Lake Monroe and the Hoosier National Forest.

Drive Time: 4 hours

What to Do: Hickory Ridge Fire Tower, B-Line Trail, Indiana University Tour, and Tibetan Mongolian Buddhist Cultural Center.

Where to Eat & Drink: Nick's English Hut on Kirkwood, Laughing Planet Cafe, Oliver Winery, Crazy Horse, Cardinal Spirits, Upland Brewing Company, and Switchyard Brewing.

Where to Stay: Nice Hotel Walking Distance to University with Free Breakfast

HANNIBAL, MISSOURI

The river town of Hannibal is all about Mr. Samuel Clemens, aka Mark Twain. The prolific American writer grew up in this charming small town and many of his tales were inspired here.

Take a ride on the Mississippi, tour Twain's boyhood home and climb in the caves he played in and helped shape his imagination.

If you want to make your trip extra memorable, visit Memorial Day Weekend when the family-friendly Twain on Main Festival takes place featuring an arts and craft event, live music, Mark Twain performers, and a wine & beer garden with local favorites.

Drive Time: 4 1/2 hours

On the Way: Route 66 (see below for stops) to Springfield (Lincoln attractions)

What to Do: Mark Twain Boyhood Home & Museum, Mark Twain Cave, Lovers Leap, Mississippi Riverboat, Memorial Lighthouse, and Cave Hollow West Winery.

Where to Eat & Drink: Fiddlesticks Food & Spirits Company, Mark Twain Brewery, Becky's Old Fashioned Ice Cream Parlor and Emporium, Becky Thatcher's Diner.

Where to Stay: No-frills Chain with Indoor Pool and Free Breakfast

Unique and Romantic B&B with Breakfast and Full Bar

ROUTE 66: CHICAGO TO SPRINGFIELD, ILLINOIS

Route 66 is the most popular road in the United States and it begins in Chicago! For a fun weekend getaway, take a ride to the state capital of Illinois.

On the way, you'll find quirky roadside attractions along with interesting small towns. There are a ton of fun photo opportunities, colorful murals, and historical places along the route.

Once you arrive in Springfield, learn about one of America's most beloved presidents, Abe Lincoln, and see where he lived and worked.

Read here for a complete Springfield Itinerary to make the most of your time in the city.

Drive Time: 5 hours

On the Way: Old Joliet Prison, Gemini Giant, Launching Pad, Funks Grove Pure Maple Sirup, Route 66 Hall of Fame, World's Largest Covered Wagon, and Paul Bunyan Statue.

What to Do: Lincoln Home, Abraham Lincoln Presidential Museum, Lincoln Tomb, Ergadoozy Creative Play Center (kids under 12), Henson Robinson Zoo, Illinois State Capitol, and Knight’s Action Park.

Where to Eat & Drink: Cozy Dog Drive-In, Obed and Isaac's Brewery, Incredibly Delicious, Engrained Brewery & Restaurant, Mel-O-Cream Donuts, and Route 66 Motorheads.

Where to Stay: Downtown Hotel with Indoor Pool

ST. LOUIS, MISSOURI

Saint Louis has it all - good food, unique museums, craft breweries, and outdoor activities.

This Midwest destination is easy on the pocketbook too with most of the attractions and museums being free.

Don't miss the Gateway Arch; one of our newest national parks with a new state-of-the-art visitor center, the City Museum; the wackiest "museum" I've ever been to, and Anheuser Busch Brewery; a tour where you can also see the famous Clydesdales.

St. Louis is a great destination for couples, families, and solo travelers with an array of vacation activities to choose from.

On the Way: For a delightful lunch on the way down, stop halfway in Bloomington at Rosie's Pub. It's a popular restaurant serving up delicious sandwiches and burgers in one of the oldest buildings in town.

What to Do: St. Louis Zoo, The Arch, City Museum, Anheuser-Busch Brewery, Forest Park, Cathedral Basilica of St. Louis, Ballpark Village, and the Missouri Botanical Garden.

Where to Eat & Drink: Bogart's Barbecue, The Fountain on Locust, Crown Candy Kitchen, Hodak's Restaurant and Bar, Civil Life Brewery, and 360 rooftop bar.

Where to Stay: Well Reviewed Hotel near the Arch with a Free Hot Breakfast & Swimming Pool

CLEVELAND, OHIO

Cleveland provides an array of attractions from action-packed sporting events to interesting museums and even a few quirky stops like Ralphie's house in A Christmas Story.

Progressive Field, the Cleveland Indians' turf, is right near the pedestrian-friendly East 4th street which is the entertainment district downtown lined with restaurants and pubs. Down the street, take your chances with Lady Luck at a casino which also happens to be in the department store where the infamous 1983 Christmas movie was filmed.

And no visit to Cleveland would be complete without the Rock and Roll Hall of Fame experience . The museum launches visitors through the evolution of the shake-rattle-and-roll era that exploded in America.

And lastly, only 20 miles south is a national park to check off your list, Cuyahoga Valley. You can explore the park on a side trip from Cleveland or Akron.

Drive Time: 5 hours 20 minutes

On the Way: Cedar Point Amusement Park

What to Do: James A Garfield Memorial, Cleveland Botanical Garden, Cultural Gardens, Rock & Roll Hall of Fame, and A Christmas Story House.

Where to Eat & Drink: Collision Bend Brewery, West Side Market, Mabel's BBQ, Great Lakes Brewery, Lindey's Lake House, Alley Cat Oyster Bar, and Fat Cats.

Where to Stay: Reasonably priced 4-star hotel with indoor pool and lake views

SHAWNEE NATIONAL FOREST, ILLINOIS

You won't believe you're still in the Prairie State once you arrive in Shawnee National Forest. It is one of the best-kept secrets in Illinois.

It's a great destination to unplug and get back to nature. Start with the 1.7 mile Rim Rock Trail which will guide you through 300-year-old oak trees and narrow crevices to a beautiful canyon.

Explore the Cave-in-Rock overlooking the Ohio River, the historic cavern provided a safe haven for frontier outlaws back in the day. Take the Cave in Rock Ferry across the river to the small Amish village in Marion.

Don't miss a sunset at Garden of the Gods and a hike up Triggs Tower for more beautiful views.

What to Do: Rim Rock Recreation Trail, Burden Falls, Triggs Tower, Bell Smith Springs Recreation Area, Cave-in-Rock, Inspiration Point, and Garden of the Gods.

Where to Eat & Drink: The Diver Down, Garden of the Gods Outpost, E'Town River Restaurant, and Hogg Hollow Winery.

Where to Stay: A Beautiful Cabin with Private Bathroom and Deck

PATOKA LAKE, INDIANA

One of the best road trips from Chicago during Covid we took was to Patoka Lake. It is a destination that offers outdoor activities, that isn't very busy especially midweek, and where you can get out on a lovely lake.

Combine the trip with visiting the small towns of French Lick, known for its historic mineral springs, and Jasper, home to the Indiana Hall of Fame.

Make sure to rent a pontoon for a day on the lake and to take a walk through the stunning French Lick Resort and West Baden Springs Hotel for a glimpse into the past.

Drive Time: 5 1/2 hours

On the Way: Stop for lunch in a booming college town - either Lafayette or Bloomington.

What to Do: French Lick Casino, French Lick Scenic Railway, and Patoka Lake State Park.

Where to Eat & Drink: Patoka Lake Winery, 33 Brick Street, German Cafe, and French Licks Ice Cream.

Where to Stay: A 3-bedroom Country Cabin on the Lake

SANTA CLAUS, INDIANA

If you are looking for a fun wholesome summer trip for the family, head over to Santa Claus, Indiana.

With free soft drinks, free parking, free sunscreen, and free Wi-Fi, you can't go wrong with a visit to Holiday World and Splashin' Safari.

Home to the world's longest water coaster and America's only launched wing coaster, both amusement parks will keep the whole family entertained.

In between, make sure to track down all the festive spots that'll have you celebrating Christmas in July.

On the Way: Lincoln Boyhood National Memorial

What to Do: Holiday World Amusement Park, Splashin’ Safari Water Park, Lincoln State Park, Santa Claus Christmas Store, Santa’s Candy Castle, Santa’s Stables, Santa Claus Museum, and Holiday Drive-In.

Where to Eat & Drink: Frosty's Fun Center

Where to Stay: Santa's Lodge just not far from the Amusement Park

Rental RVs and Holiday Cabins

PUT-IN-BAY, OHIO

Where should I go for a weekend getaway from Chicago? Let me introduce you to South Bass Island in Ohio that is home to the small charming village of Put-in-Bay.

Even though there's plenty to do for families, this Midwest must-experience destination is best for couples or friend getaways. It's where golf carts roam and drinks flow with over 25 bars, breweries, and wineries.

From boating to paddle boarding, water activities are one of the best things to do when visiting. Along with catching a sunset at South Bass Island State Park, touring the wineries, and eating and drinking your way through town.

Drive Time: 5 1/2 Hours

On the Way: Shipshewana, Indiana's cutest Amish town.

What to Do: Observation Deck at Perry’s Victory and International Peace Memorial, island tour by tram, bike, or golf cart, Heineman’s Winery and Cave Tour, the monument view from Oak Point State Park, swimming at The Sand Bar, and the Massie Cliffside Preserve.

Where to Eat & Drink: Put-in-Bay Brewery, Chocolate Cafe & Museum, The Forge, Put-in-Bay Winery, Biergarten at the Boathouse, The Boardwalk, and Topsy Turvey's Bar & Grill.

Where to Stay: A Private Guesthouse with Free Bikes and a Fabulous Breakfast

AKRON, OHIO

Where can I go 6 hours from Chicago? Akron, Ohio that's where!

This is a city that surprised us in so many ways, not to mention, it's right next door to one of the few national parks in the Midwest.

Catch a minor league baseball game, tour an incredible historic mansion, chase waterfalls in Cuyahoga National Park, and visit an impressive art museum.

Drive Time: 6 hours

What to Do: Akron Art Museum, Cuyahoga Valley National Park, Akron Rubber Ducks, Stan Hywet Hall, and Akron Civic Theatre.

Where to Eat & Drink: The Peanut Shoppe, Mr. Zub's Deli & Bar, Lock 15 Brewing Company, and El Patron Tequileria & Cuisine.

Where to Stay: Modern Hotel with Lounge and Indoor Pool

TWIN CITIES, MINNESOTA

Saint Paul and Minneapolis, commonly called the Twin Cities, have a lot to offer for a vacation.

St. Paul is a little quieter with the state capitol and more daylife. While Minneapolis is where you go for art, theater, and nightlife. Both have a ton of breweries and great food options.

Discover the area through fun attractions like the Mall of America, the Science Museum of Minnesota, Como Zoo, Can Can Wonderland, and the Walker Art Sculpture Garden.

And do not miss the most beautiful places like the Cathedral of Saint Paul, the Minnesota State Capital, Como Conservatory, the historic homes of Summit Avenue, Lake Phalen, and Minnehaha Falls.

On the Way: Eau Claire, an Underrated Wisconsin Destination.

Where to Eat & Drink: Band Box, Summit Brewing Company, Keg and Case Market, Bad Weather Brewing, The Anchor Fish & Chips, and The Nook.

Where to Stay: Hotel with a Free Shuttle and Modern Rooms

CLEAR LAKE, IOWA

Clear Lake is a little hidden gem in the state of Iowa and it's another destination only 6 hours away from Chicago.

Cruise the Lady of the Lake, an authentic paddlewheel boat, while taking in the sights and learning some fun facts about the area.

Take in a show and tour The Surf Ballroom, where Buddy Holly, Ritchie Valens, and JP “The Big Bopper” Richardson played their last concert. Frozen in time, it'll transport you right back to 1959.

Eat, drink, and shop along Main Avenue, the hub of this friendly lakefront community.

And before you leave, drive north to Buddy Holly's Crash Site, you can't miss the giant Holly's iconic black eyeglasses.

On the Way: Galena's Helluva Half Mile Main Street

What to Do: Lady of the Lake Cruise, The Surf Ballroom & Museum, Clear Lake State Park, and Central Gardens of North Iowa.

Where to Eat & Drink: Cabin Coffee, Starboard Market, PM Park, South Shore Donuts, Lake Time Brewery, and Sevens Steak House.

Where to Stay: Adorable Rental with Free Bicycles walking distance to the Surf & Downtown

PORCUPINE MOUNTAIN STATE PARK, MICHIGAN

Michigan's Upper Peninsula is pleasant in the spring and summer, but it is also one of the best fall road trips from Chicago. And no trip there is complete without a visit to the Porcupine Mountains Wilderness State Park.

With 60,000 acres of old-growth forest, meandering rivers, jaw-dropping vistas, and flowing waterfalls, the “Porkies” will impress any traveler. It's kind of hard to believe you can find these views in the Midwest!

Drive Time: 6 hours 40 minutes

On the Way: Oshkosh, Wisconsin.

What to Do: Bond Falls, Lake of the Clouds, Escarpment Trail, Presque Isle Falls, Summit Peak Observation Tower, Big Carp River Trail, Union Spring Trail, and Porcupine Mountains Chairlift.

Where to Eat & Drink: White Pine's Yooper Diner, Antonio's Restaurant, and Hoop'n Holler Tavern.

Where to Stay: Chain Hotel only 15 minutes from the Park

RED RIVER GORGE, KENTUCKY

Listed on the National Register of Historic Places and a National Natural Landmark and National Archaeological District, Red River Gorge is a place that should not be overlooked as a road trip from Chicago.

Located in the Daniel Boone National Forest, there are over 100 natural sandstone archways, waterfalls, dense woodlands, exposed limestone ledges, tunnels, and bridges. 

Red River Gorge is an outdoor enthusiast's dream destination.

Drive Time: 7 hours

On the Way: Kentucky Horse Park in Lexington

What to Do: Nada Tunnel, Sheltowee Trace National Recreation Trail, Gladie Historic Site and Visitor Center, Sky Bridge Trail, Angel Windows Trail, Chimney Top Rock Trail, Cliff Trail, and Hidden Arch.

Where to Eat & Drink: Sky Bridge Station, Red River Rockhouse, Thatcher Barbecue Company, and Miguels Pizza.

Where to Stay: Great Resort surrounded by Natural Beauty

KANSAS CITY, MISSOURI

We are moving onto longer drive times so anything below here are my recommended best road trips from Chicago for a week or more.

Kansas City has culturally rich areas, bold and modern architecture mixed with distinguished historic buildings, a flourishing arts scene, and finger-licking-good barbecue.

If that doesn't convince you, it is also home to the best World War I Museum in the country and a highly rated art museum admired by all that visit.

Drive Time: 7 hours 45 min

On the Way: Springfield, Illinois.

What to Do: Crossroads Art District, National World War I Museum, Nelson-Atkins Museum of Art, City Market, Rose Garden at Loose Park, and Country Club Plaza.

Where to Eat & Drink: Arthur Bryant's, Cinder Block Brewing Company, Gillis Cafe and Hangout, Pigwich, Joe's Kansas City Bar-B-Que, and Boulevard Brewing Company.

Where to Stay: Hotel with Ideal Location and Free Breakfast

BRANSON, MISSOURI

Branson is probably one of the most underrated road trips from Chicago for families.

It's not just cheesy musicals and religious shows, there's a lot of natural beauty, fun attractions, and cool things to do for kids and adults alike. 

Drive Time: 8 hours

On the Way: St Louis and the quirky stop of Uranus.

What to Do: Titanic Museum, Silver Dollar City Amusement Park, Table Rock Lake Trail, Dick’s 5 & 10 Store, Top of the Rock, Shepherd of the Hills Fish Hatchery, and Branson Landing.

Where to Eat & Drink: Danna’s BBQ & Burger Shop, White River Fish House, Andy’s Frozen Custard, The Paddlewheel, Clockers Cafe, and Mel's Hard Luck Diner.

Where to Stay: Modern Hotel on the Branson Landing

FINGER LAKES, NEW YORK

If you are interested in 10 hour road trips from Chicago, Finger Lakes is the place to go especially if you enjoy hiking, lakes, and drinking.

The region is renowned for its wine trail but it also has more than 75 craft breweries! Don't miss the wonderful state parks and the interesting towns of Hammondsport and Corning.

Drive Time: 10 1/2 hours

On the Way: Rock n Roll Hall of Fame in Cleveland.

What to Do: Watkins Glen State Park, Corning Glass Museum, Hammondsport, Robert H. Treman State Park, and Mark Twain's Study and Burial Site.

Where to Eat & Drink: Market Street Brewing Company and Restaurant, Glenora Wine Cellars, Rooster Fish Brewing Tasting Room, Nickel's Pit BBQ, and Wagner Vineyards Estate Winery.

Where to Stay: Inn with a Beautiful Grounds & a Free Breakfast

BLACK HILLS, SOUTH DAKOTA

If you're planning a 2 week road trip from Chicago, head to the beautiful Black Hills of South Dakota.

You'll find scenic drives, history, wildlife, and natural beauty throughout the entire region. And, some goofy roadside attractions on the way!

Drive Time: 14 hours

On the Way: Austin, Minnesota

What to Do: Wildlife Loop in Custer State Park, Mount Rushmore, Wind Cave National Park, Evans Plunge Hot Springs, Crazy Horse Memorial, and Badlands National Park.

Where to Eat & Drink: Chuck Wagon Dinner Show, Baker’s Bakery & Cafe, Black Hills Burger & Bun Co, Wall Drug, and Legion Lake Lodge. 

Where to Stay: Bavarian Inn with an Outdoor Pool

THEODORE ROOSEVELT NATIONAL PARK, NORTH DAKOTA

If you like cool roadside attractions, quirky vibes, outdoor adventure, and getting off the beaten path then this is one of the best long road trips from Chicago.

Don't put off North Dakota as your last state because it has a lot going for it. The Theodore Roosevelt National Park has sprawling natural beauty with winding waterways and painted canyons along with free-roaming bison and wild horses.

The neighboring town of Medora is one of my favorite small towns in the U.S. with an authentic Western energy. Visit the Cowboy Hall of Fame to learn about cowboy culture, catch a show at the famous Medora Musical, an outdoor extravaganza with the real badlands as its backdrop, and stroll the streets of this tiny charming town.

On the Way: Fargo-Moorhead Visitors Center, Fargo Air Museum, Frontier Village, World's Largest Buffalo, Lewis and Clark Riverboat, Fort Abraham Lincoln State Park, North Dakota Heritage Center and State Museum, North Dakota State Capitol, and the Enchanted Highway.

What to Do: The Medora Musical, Chateau de Mores State Historic Site, Pitchfork Steak Fondue, ND Cowboy Hall of Fame, South Unit 36-mile Loop Drive, Sunset at Wind Canyon, Painted Canyon Visitor Center Overlook, Ridgeline Nature Trail, Roosevelt’s Maltese Cross Ranch Cabin, Boicourt Trail, Buck Hill Trail, Oxbow Overlook, River Bend Overlook, Cannonball Concretions Pullout, and 14-mile North Unit Scenic Byway at the Theodore Roosevelt National Park.

Where to Eat & Drink: Sandy's Donuts, Drekker Brewery, Tower Travel Center, Little Missouri Saloon & Dining Room, Medora Uncork'd, and Hidden Springs Java.

Where to Stay: Ranch Cabin in the Heart of Medora

Hotel with Free Breakfast and Indoor Pool

One of the most beautiful Midwest states is just a short drive from Chicago, here are fun day trips in Michigan to help you plan. 

I hope you enjoyed my favorite road trips from Chicago 2021 edition! If you have any other recommendations, please let us know in the comments below!

• About Author
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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

Latest posts from Angela

• The Best Things to Do in South Haven, Michigan - July 15, 2024
• Explore Indiana Amish Country: A Perfect Weekend Itinerary - July 8, 2024
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Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 09/26/2024

Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater. 

You want to get out of town with minimal effort and do not want to spend a small fortune to do it. 

To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest. 

Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

Or view all 30+ places we recommend going in the map below.

How to use this map:  In the map header, click the square tab to the left of my logo or click the enlarge frame to the right to view detail. You can save the map to “Your Places” on Google Maps by clicking the star next to the map name. Or you can share it by clicking the share icon.

Wisconsin: Top Road Trips Within 5 Hours of Chicago

Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.

Check out these six Wisconsin destinations shared in more detail below.

• Madison, WI
• Milwaukee, WI
• Sheboygan, WI
• Door County, WI
• Wisconsin Dells, WI
• Lake Geneva, WI

Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away . This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.

If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.

Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.

While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant , Green Owl Café — don’t miss their loaded vegan cheese fries.

When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.

The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here .

Sign up for my monthly Discovery Newsletter & get a free Trip Budget Calculator !

Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

Milwaukee, Wisconsin , is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.

There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.

There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum , a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World , Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!

Stay at the Plaza Hotel , centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere , a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.

One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum . You can’t miss it—there is a ship’s hull sticking out of the building! While downtown, stroll 8th Street for delicious pizza at Il Ritrovo , and don’t miss the Victorian Chocolate Shoppe . Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks .

Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here . 

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days. 

We visited Door County in the fall , and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks . 

We even visited Cave Point County Park , one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.

In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities. 

With over 300 miles of shoreline , you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day.  Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.

Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay . Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor . Top family-friendly resorts include Newport Resort , Ephraim Shores Resort , and Scandinavian Lodge . Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door. 

Search all family-friendly Door County lodging options on VRBO or Booking.com .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World . The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway . Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?

The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.

The best place to stay in Wisconsin Dells is one of the Waterpark Hotels . Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.

The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.

Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path , a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.

For accommodation, The Abbey Resort , located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here .

Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago

Experience the best of the Mitten State , a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes —will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.

Check out these four Michigan & Ontario destinations shared in more detail below.

• Saugatuck, MI
• Ann Arbor, MI
• Detroit, MI, into Ontario, Canada (a loop driving trip)
• Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)

To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids .

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

We love Saugatuck. We have visited for weekend trips several times in the fall and summer and keep returning for more. What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.

Our favorite beaches are Oval Beach , which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan.  Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park , which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches. As well as Douglas Beach Park for the sparser crowds and sunsets.

When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share 30+ of the best things to do here . And even created this top 10 fall activity list just for families.

Visiting families also love going on Saugatuck Dune Rides . This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational. 

For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner , where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions , and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider .

Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “ Saugatuck, MI: 8 Amazing Areas to Search for Lodging .” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “ Roundup of the Best Family-Friendly Places to Stay in Saugatuck .”

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit!  From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours , making it a perfect road trip for a few days away!

Ann Arbor is well known for its thriving arts and culture scene . Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair . The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.

For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.

When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.

When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor . Or search for more Ann Arbor lodging options here .

Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario , Canada.  This southernmost region of Canada is filled with quaint small towns, sandy beaches , an abundance of fruit farms and wineries , and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s. 

From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada. 

Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border , where you’ll loop back to Chicago:

• Optional overnight at Caesar’s Windsor Hotel , or search for other Windsor lodging .
• Or, Pelee Island : Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B , or other lodging . 
• Grand Bend Beach : Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
• Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel , in Sarnia . Or stay search for other nearby lodging .
• Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

We visited vibrant Traverse City, MI , picturesquely nestled at the southern u-shaped end of Grand Traverse Bay , for five days in the heart of summer with our family dog and loved every minute of our trip. 

In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking. 

We walked the paths in Grand Traverse Commons Natural Area , located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit. 

On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park , stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery .

Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail , one of many in the area , and relaxed and picnicked on dog-friendly Esch beach. 

In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families. When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort . Or search for a rental in the area. Find more available Traverse City hotels and lodging here . 

Indiana: Top Road Trips Within 5-Hours of Chicago

Hang out in the Hoosier State in one of these two top destinations:

• Indiana Dunes National Park, IN
• Indianapolis, IN

Additionally, consider staying in French Lick, IN, at the French Lick Resort  (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.

In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.

Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park .

If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage . The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks , expect a visit to Indy will be a memory-making trip your kids will love.

Top spots include the Indianapolis Children’s Museum , which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world!  While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.

Prefer outdoor activities?  Be sure to visit the Indianapolis Zoo and White River Gardens , where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing. 

For families who love cars and racing, include a visit to the Indianapolis Motor Speedway . Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.

On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy? The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis , with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here .

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

• Starved Rock State Park, IL
• Shawnee National Forest, IL

Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging , some with pools.

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!  

If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features . Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.

Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.

Other top features of the park include hiking, boat tours, and camping . And perhaps the park’s biggest draw—the entrance is free !

Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here .

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families. 

One of the best things about Shawnee National Forest is its variety of activities , such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone.  Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs. 

When looking for a place to stay, consider the location of your planned activities . Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be. One excellent lodging option for families is Home2 Suites in Carbondale , which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here . Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins , which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois !  Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge , it is the perfect place to spend a fun weekend.   

Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.  

To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge , where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf.  Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12 . 

There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel , Union Station , and spend your time exploring the many family-focused activities that Saint Louis offers.  First, take your family to explore the City Museum . Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline. 

Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils. 

No family road trip to St Louis is complete without a trip to Forest Park— one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum , the Saint Louis Science Center , the Missouri History Museum , an outdoor theater, and the Saint Louis Zoo . Entrance fees vary, but many amenities, including general admission to the zoo, are free!

Want to see more St. Louis lodging options ? Search for other family-friendly accommodation options here .

Ohio: Top Road Trips Within 5-Hours of Chicago

From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors , and especially families, with all it offers as a vacation destination.

Four Buckeye State destinations to consider for your next road trip include:

• Cincinnati, OH
• Cleveland, OH
• Cuyahoga Valley National Park, OH
• Cedar Point Amusement Park, OH

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio.  After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.

So, start your visit with a trip to The Cincinnati Art Museum , founded in 1881, and in the Eden Park area.  Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution. 

Next, grab a picnic lunch and explore Ault Park , which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.

Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati , where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here .

Cleveland, Ohio

A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).  Stay in town at a place like centrally located and highly-rated Roost Cleveland , which offers fully furnished apartments with hotel-like perks,  and use it as a base to explore the area. 

The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore.  And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.

For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park , a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.

Want to see more Cleveland lodging options ? Search for other family-friendly accommodation options here .

Cuyahoga Valley National Park, Ohio

Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park .  Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities. 

Families can explore the park’s hiking trails , go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride.  With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.  

If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village , a private island of town surrounded by Cuyahoga Valley National Park.  Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO  to find them.

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

Cedar Point Amusement Park , located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun. 

Known as the “ Roller Coaster Capital of the World ” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining.  Take at least two days to enjoy all it has to offer.

Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers , Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel .

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park. 

While in the area, catch a ride on a riverboat like the Belle of Louisville , which offers several different types of cruises, including historic narrated ones to picnic lunch cruises . Or your whole crew might love the Hometown Music Kids Cruise , designed especially for families.

Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory , conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.

Need an indoor day activity? Explore the Mega Cavern , a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo.  Or visit the downtown Kentucky Science Center , where your kids can engage with exhibits about the human body and outer space.

For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here . 

Related Reading

For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.

• Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
• 31 Warm Winter Break Vacation Ideas Your Family Will Love
• Enjoy the Ride: 12 Tips for Better Family Road Trips
• 15 Tips on How to Raise the Bar on Rental Cars
• Pack Faster & Better With This Universal Printable Packing List
• 25 Expert Packing Tips to Help You Travel Better
• Pre-Trip: A Practical Checklist to Close the House & Pack

Additional Trip Planning Resources

To further help you with travel planning, I share my go-to resources for every trip below. 

Google Flights. My first research stop for affordable flights for every trip. Learn why here . 

Google Hotels . Use its “ Where to stay ” button to discover the best neighborhoods to base your visit.

Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.

Viator , Get Your Guide , & Airbnb Experiences . Quickly find and book highly-rated tours and activities on these sites.

Google Travel Things to Do & Google Maps . Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list. 

AllTrails . Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.

Guide Along . 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour .

Insure My Trip. I never travel internationally without trip insurance. Learn why here . My preferred place to shop and compare policies is InsureMyTrip.com . 

Plus, check out the 15 travel apps I use on trips, my preferred guidebooks , and my free customizable travel itinerary template , downloadable in four file formats.

About the author : Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog, Gather and Go Travel . After attending the University of Michigan undergraduate business school and following a career in retail strategy and event management, she returned to focus on her first love—travel. Read her bio , learn how she became a blogger , and discover how to work with her . Sign up for her monthly Discovery Newsletter to get her latest travel recommendations and how-to’s .

Love to travel? Sign up for m y monthly Gather & Go Travel Discovery Newsletter and get a free trip budget calculator.

Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.

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Welcome to  Gather and Go Travel , a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, a world traveler to 50+ countries, a travel writer/blogger, and a book lover. Learn more  about me , read  our story , and how to  work with me . Get my latest updates, how-tos, and trip ideas in my monthly  Discovery Newsletter .

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23 Best Family Road Trips from Chicago

Chicago's got it all - from its towering skyline and delicious deep-dish pizza to a cultural scene that's second to none. The city also boasts an amazing location and if you're on the hunt for your next family getaway, you're in luck. The Midwest is full of places that are just a drive away from Chicago.

On our list of 23 best family road trips from Chicago, you will find everything from amusement parks and peaceful nature retreats to fascinating historical sites and hands-on museums. There's something out there for families of all shapes and sizes.

That's exactly why we've put together a go-to list of the best family road trips from Chicago. So get your car games ready, and pack your books and keep reading to discover our top picks for family road trips, including how far you'll need to travel and what exciting attractions await at each destination.

Below, you will find our shortlist of amazing adventures on the road for all the family members, young in age or young at heart!

Best family road trips from Chicago: a quick overview

But that's not all; there are many other road trips you can enjoy from Chicago. If you are traveling during spring break, you can refer to our best spring break road trips from Chicago . Alternatively, for the colder months, you can check out our guide to the best winter road trips from Chicago .

Not sure when you want to travel and want to be inspired? You can find amazing ideas in our guide to the best road trips from Chicago .

Family-friendly day trips from Chicago (under 3 hours each way)

Day trips are perfect getaways, especially if you are traveling with younger children, and there are so many amazing places to visit with family near Chicago. From amusement parks to interesting museums, you will be spoilt for choice!

45 minutes from Chicago (40 miles)

Why visit Gurnee with family? The shortest drive on our list, which is perfect for a day trip, Gurnee is home to numerous theme parks, water parks and shopping centers.

Even though Gurnee is not exactly a city on its own but a suburb of the Chicago metropolitan area, there was no way we could not include this amazing location on our list of family road trips.

The town is also known for lovely beaches, hiking and biking. With these attractions, Gurnee is truly a premier family destination on Lake Michigan.

Driving to Gurnee from Chicago: The drive from Chicago city center to Gurnee is quite straightforward. Just follow Interstate 94 (I-94) north and then take US-41 to reach your destination.

Our highlights: Six Flags Great America is a wonderful theme park for travelers of any age. Here, you can enjoy a double-decker carousel, an atmospheric County Fair section or the themed Yukon Territory Section, or take a ride on the thrilling roller coasters.

Great Wolf Lodge's indoor water park is a fabulous family destination. It is a whole world of play, with various slides, pools, adventurous attractions, and a children's play area.

Once you have had your fill of thrills, Gurnee Mills is a large shopping center with over 200 stores and plenty of restaurants and cafés to enjoy.

If you are in the mood for a more serene afternoon with your family, you can pack a picnic and enjoy the waters and scenery of Lake Michigan at Illinois Beach State Park.

Did you know? On average, 23 million visitors find their way to Gurnee every year, showing the popularity of this Chicago suburb on Lake Michigan!

Things to note: Gurnee is close to Chicago and a popular destination, so traffic is often fairly busy on this stretch. Be vigilant on the road, especially if you're going to Gurnee in winter and snowy conditions.

Six Flags Great America is temporarily closed, but it is set to reopen this year. Please check before traveling to avoid any disappointment.

2. Harbor Country

Via indiana dunes national park.

1 hour 25 minutes from Chicago (75 miles)

Why visit Harbor County with family? Harbor Country, on the southwestern shore of Lake Michigan, is a great day trip destination for the entire family. It is just a short drive away from Chicago, and what draws people here are the lovely beaches, bed and breakfasts, and vineyards.

The area is also known for beautiful hiking, birding, swimming, and other lake-based activities. For families, there are also amazing farmers' markets, family-owned farms, and more to enjoy.

Driving to Harbor County from Chicago: Head south on I-90 out of Chicago and follow the shore until you reach Indiana Dunes National Park. From here, you will switch to I-94, heading east to reach Harbor County.

Our highlights: Indiana Dunes National Park is a top lakeside destination on the way to Harbor Country. On top of swimming and exploring the dunes, you can do bird watching and learn about the various vegetation types found in the area, from shorelines to wetlands, prairies and oak savannahs.

Hesston Steam Museum is a great place for the entire family to visit. You can take a ride on a real steam-powered train through the countryside, learn about the history of steam engines that enabled much of the development in these regions, and enjoy refreshments at a restaurant.

Three Oaks Market, in downtown Three Oaks, takes place every Friday afternoon, and it offers the freshest food, produce, and artisanal goods the region has to offer.

Captain Mike's Fun Park in Lake Charter Township is open during summer. This five-acre park offers go-karts, bumper boats, putt-putt courses, snacks, and more.

Fernwood Botanical Garden, slightly inland close to Buchanan, offers wonder, beauty and family fun. On top of a regular arboretum, there is also an adventure garden, nature trails, an education center, and more to enjoy at this beautiful venue.

Did you know? This area is known for its beautiful beaches along Lake Michigan, making it a popular spot for finding Petoskey stones, Michigan's state stone. So see if you can tell the difference between different rocks and find one of these special stones with the little ones!

Things to note: Roads to Harbor Country are in good condition; just be aware of the chance of snow in the winter months.

There are lots of lovely, smaller country lanes in this region that you might want to explore slowly during your trip for views of the rolling hills, forests, and farms.

3. Lake Geneva

1 hour 40 minutes from Chicago (80 miles)

Why visit Lake Geneva with family? Go lake -hopping with your family! This road trip will not only take you to Lake Geneva but also to Lake Zurich and Fox Lake for the ultimate waterside adventure.

Lake Geneva is also a wonderful day trip or weekend destination for the family, including your little ones. With parks and playgrounds, walking trails, beaches, magic theaters and more, there is much to see and enjoy for everyone.

Driving to Lake Geneva from Chicago: Follow I-90 northwest and hop onto IL-53. You will soon reach Lake Zurich. After your visit, your next stop will be Fox Lake, and then US-12 will take you all the way to Lake Geneva.

Our highlights: Walking trails, slides, swings, and picnic tables can be found at Oak Ridge Marsh Park Playground by Lake Zurich on the way to Lake Geneva.

If you wish to head to the beach with your children, Riviera Beach on Lake Geneva is a good option. It is enjoyed by swimmers, sunbathers, hikers, and boaters alike.

At the small Tristan Crist Magic Theater, you can witness magic and illusion shows that are family-friendly and be amazed!

At Lake Geneva Ziplines & Adventures, your family can explore sky bridges and rope courses and take a zip line ride through the forest. The area also includes hiking and biking trails.

Did you know? Famous for its grand estates and as a former retreat for wealthy Chicago families, it's also known for being the birthplace of the tabletop role-playing game Dungeons & Dragons!

Things to note: Tristan Crist Magic Theater is the region's premier entertainment option, and it is a good idea to book tickets in advance if possible.

4. Peru and LaSalle

1 hour 30 minutes from Chicago (100 miles)

Why visit Peru and LaSalle with family? Peru-LaSalle twin cities provide much to enjoy for the entire family, from beautiful natural getaways to historic sites and a vibrant downtown area to explore with shops and restaurants. They are fabulous destinations from Chicago.

La Salle and its twin city, Peru, make up the core of the Illinois Valley. La Salle, or LaSalle, is known for its many historic sites, such as a replica canal boat and the Hegeler-Carus Mansion.

Driving to Peru and LaSalle from Chicago: Head northwest on I-55 and then switch to I-80 to reach LaSalle. Peru is a short drive from here on US-6.

Our highlights: Starved Rock State Park on the Illinois River is known for its sandstone canyons, some of which have waterfalls. The park has many in wooded trails and fascinating wildlife, and there are lovely viewpoints overlooking the river - perfect for a family outing.

Buffalo Rock State Park in LaSalle County contains a riverside bluff and almost 300 acres of nature, with walking trails, camping sites and fabulous picnic sites.

Visit the I&M Canal National Heritage Area to get a real feel of the life of the American frontier. Little ones traveling with you will especially love the 1880s replica Canal Boat and enjoy taking a boat tour of the canal, which starts with a crash course on “Mule Tending 101”!

Hegeler-Carus Mansion, built in 1874, is a grand Victorian-era home of 57 rooms and is a fascinating place to visit with the family. It features fine details all around; on its hand-painted walls and ceilings, beautiful woodwork, chandeliers, and large glass windows.

Things to note: Starved Rock and Buffalo Rock state parks are open all year round. In winter, it can be particularly special to visit Starved Rock State Park, to view the frozen waterfalls.

As with all roads in Illinois, winter months can see the roads covered in snow at times; be aware of this should you be doing the road trip in winter.

5. Milwaukee

Via kenosha.

2 hours from Chicago (110 miles)

Why visit Milwaukee with family? Milwaukee is a beautiful and fun city on the shore of Lake Michigan, home to splendid historical and cultural attractions for the younger members of the family as well as famous breweries for the parents!

Milwaukee is an easy 2-hour drive away and has lovely attractions for family members of all ages to explore, including museums, a zoo, a science center, shops, and great restaurants.

Driving to Milwaukee from Chicago: Follow I-94 heading directly north and then hop on WI-158 to visit Kenosha. Retrace your steps after your visit to get back on I-94 to arrive in Milwaukee.

Our highlights: In Kenosha, on the way to Milwaukee, you can visit the Dinosaur Discovery Museum to view dinosaur fossils - something exciting for all of the family members.

Milwaukee Public Museum is home to natural and human history exhibits. This museum is great to explore with children, and there is also a restaurant and a dining area.

If you want to visit other museums, Discovery World Science and Technology Museum is another must-see destination for families visiting Milwaukee.

Alternatively, you can visit Milwaukee County Zoo, home to over 3000 animals from 350 different species. This popular zoo receives 1,3 million visitors a year!

Did you know? Milwaukee is known for its major league baseball team, the Milwaukee Brewers, and its unique mascot, Bernie Brewer.

Things to note: Milwaukee winters are known to get cold, and driving conditions may be impacted by snow blizzards if you're doing this road trip in winter. Check ahead of time and prepare accordingly. Fortunately, the city has much to offer in warm and colder seasons!

6. South Bend and Mishawaka

2 hours 10 minutes from Chicago (100 miles)

Why visit South Bend and Mishawaka with family? Visiting South Bend and Mishawaka makes for a lovely trip for the family. South Bend is a university town home to affordable restaurants and fantastic playgrounds.

Both South Bend and Mishawaka areas are famous for the wonderful parks and trail systems present here, as well as for museums, galleries, shopping, and historic spots. These include historic parks, sky-high playgrounds, and green areas with beautiful nature trails.

Driving to South Bend and Mishawaka from Chicago: Heading out of the city in the southeast direction, follow I-90 and then IL-2 to drive into La Porte. From here, the same highway will take you to South Bend and then Mishawaka to the east.

Our highlights: Sky Zone Trampoline Park in Mishawaka offers tons of fun indoors. You can buy single-day passes to access the various activities offered at this park. You can expect lots of bouncing, playing, jumping and flipping here!

The entire family can enjoy a day of entertainment at the Strikes and Spares Entertainment Center. Activities available include go-karts, bowling, mini-golf, and bumper cars. Food and drinks are also available and a toddler area for the youngest members of the family.

Potawatomi Zoo is a zoological park in South Bend. There are animal exhibits and educational programs at the zoo, and even train rides available for the family to enjoy.

At South Bend Chocolate Co. Factory you can get behind the scenes and take a tour to explore the factory floor and observe how the best chocolates are made. The perfect way to spend the afternoon, especially if you or your family have a sweet tooth!

Meanwhile, at The History Museum's Kidsfirst Children's Museum, children have a chance to get a close look at the area's local history and the way of life of the pioneers in South Bend.

Central Park is a popular park in Mishawaka, with a splash pad, playground, and the river running through the park with lovely walking trails alongside it.

Did you know? There are a few explanations as to the origin of the name Mishawaka. It may have derived from the local Potawatomi language in which it would have meant "firewood-tree land".

Alternatively, it might come from the name of a local chief's daughter who, long ago, fell in love with a white trader. She was a princess, also giving the city its nickname, the "Princess City".

Things to note: South Bend and Mishawaka area is especially a good choice for a family trip during the winter time, because of the many indoor attractions present here, as well as the opportunity to enjoy ice skating and other outdoorsy winter activities.

Via Indiana Dunes National Park and Michigan City

2 hours 50 minutes from Chicago (150 miles)

Why visit Holland with family? Circling the southern and eastern shores of Lake Michigan, this road trip will allow you to explore the beaches, dunes and scenic sights along the way, and it eventually takes you to unique Holland, with lovely cycling routes, and tulip fields.

Holland is best known for its Dutch heritage, which is visible in the city's identity. For families, there are plenty of fun activities: explore the area's parks for hiking, picnicking, and playing, or go swimming, paddle boarding, or boating on the lake Macatawa that the city surrounds.

Driving to Holland from Chicago: Follow I-90 out of Chicago and follow the coast towards Indiana Dunes National Park and then Michigan City. From here, I-94 and then I-196 will take you to Holland.

Our highlights: Indiana Dunes National Park is an exciting family-friendly destination. It runs for 20 miles along the shore of Lake Michigan, offering plenty of opportunities to explore the coastline and the dunes. This is also a highly biodiverse area, with a mix of forests and vegetation types to admire and hike through.

Washington Park Zoo in Michigan City is full of magic. This historic zoo, spread out over natural hillside terrain, is home to numerous animals that come from conflicting backgrounds and would not be able to live out their lives in the wild anymore.

Instead, the tigers, tamarins, alligators, and many other animals housed here are now great educators about the natural world for children and adults alike.

Holland State Park in Holland is also a great destination if you're visiting with your children. You can observe deer and migratory birds here, and there are also snack shops and a lovely big playground at the park.

Windmill Island Gardens is home to a 250-year-old windmill called De Zwaan. You can also admire tulip fields and gardens in this beautiful destination.

Outdoor Discovery Center is another fascinating attraction. This nature preserve has an educational facility with exhibitions on native animals, and it also has play areas for children.

Did you know? In Holland, Michigan, you really feel at times like you could be in the Netherlands! Each year, a Tulip Time Festival takes place, during which tulips are seen, planted and exhibited around the city.

Things to note: Should you wish to truly admire the wonderful tulips, visit Holland in May when the Tulip Time Festival takes place.

Indiana Dunes State Park is open all year round, though some hiking trails are closed during the winter months.

Via Rockford

2 hours 50 minutes from Chicago (160 miles)

Why visit Madison with family? Madison is an all-around interesting, big city to explore, and it makes a great day or longer vacation destination from Chicago. If you're visiting with your family, there are plenty of indoor and outdoor attractions to enjoy and explore.

With a free zoo, a large farmer's market, plenty of exciting museums and over 250 parks, you will find plenty to do and explore with your family in Madison.

Driving to Madison from Chicago: Out of Chicago, I-90 will take you northwest to Rockford. From here, the interstate will head directly north to Madison.

Our highlights: Discovery Center Museum at Rockford, Illinois, hosts over 250 interactive exhibits and offers fun and educational activities for both children and their parents.

Henry Vilas Zoo in Madison is another great family destination in this beautiful city. The zoo offers free entry and is home to animals from all over the world.

Dane County Farmer's Market runs on Saturday mornings between April and November. This large farmer's market has a superb selection of produce and snacks for the little ones!

Madison Children's Museum is a must-visit attraction if you visit Madison with your children. This museum for children contains exhibits on arts, sciences, history, culture, and much more.

Things to note: The roads between Chicago and Madison are generally kept in great condition. Of course, if doing this road trip during winter months, you'll need to be prepared for snowy conditions on the roads.

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Family-friendly weekend trips from Chicago (3-5 hours each way)

Have a holiday that conveniently coincides with a Monday? Then, these weekend and long weekend trips from Chicago will be amazing drives to enjoy with your family. From charming coastal towns to buzzing cityscapes, you will have plenty of options to choose from.

9. Galena and Chestnut Mountain Resort

3 hours from Chicago (170 miles)

Why visit Galena and Chestnut Mountain Resort with family? This road trip takes you to the fascinating city of Galena, with great attractions for the entire family to explore. You will also get to enjoy great skiing and snowboarding at the nearby Chestnut Mountain Resort.

Galena attracts around a million visitors each year to admire its old-town charm, cobbled streets, and historic buildings, stroll through the city's many antique shops and wineries, or explore the hilly country surrounding the Mississippi River.

Driving to Galena and Chestnut Mountain Resort from Chicago: You will follow I-90 from Chicago until you reach Rockford and then hop onto US-20 to head into Galena. From here, W Blackjack Road will take you to Chestnut Mountain Resort.

Our highlights: When taking this road trip from Chicago, we recommend stopping at the Discovery Center Museum in Rockford on the way to explore their 250 interactive exhibits and workshops.

Once you arrive in Galena, you can take in the views and listen to the stories of the historic Galena on a city tour provided by Galena Trolley Tours.

P.T. Murphy Magic Theater offers an intimate, magical performance experience at a small 24-seat private theater in the historic heart of Galena.

Chestnut Mountain Resort, on a ridge overlooking the Mississippi River, offers skiing and snowboarding slopes for all levels. The resort also offers river cruises, an indoor pool, restaurants, and wonderful lodging options.

Things to note: The drive to Galena from Chicago along US-20 is generally a smooth one, just be prepared for snowy conditions in the wintertime.

Galena itself offers much to see and do in all seasons, and in winter, the historic city is adorned in colorful Christmas decorations, which only make the atmosphere more cheerful and festive!

It is good to book tickets in advance for the P.T. Murphy Magic Theater show because the theater only has 24 seats.

10. Sheboygan and Manitowoc

Via milwaukee.

3 hours from Chicago (175 miles)

Why visit Sheboygan and Manitowoc with family? If you're traveling to Sheboygan and Manitowoc with your family, you're in for a treat on the western shores of Lake Michigan. You'll find a great array of attractions and activities to enjoy here, from scenic parks and beaches to engaging museums and water parks.

Sheboygan is especially known as the outdoor enthusiasts' heaven because of its location and geography: it is dubbed the world's Freshwater Surf Capital, and Lake Michigan also offers much else to a visitor in the form of fishing, sailing, and long sandy beaches. Manitowoc is also known for water-based activities and attractions.

Driving to Sheboygan and Manitowoc from Chicago: Follow I-94 until you reach Milwaukee and then switch to I-43 to visit Sheboygan and then Manitowoc.

Our highlights: On the way to Manitowoc, you might want to stop at Milwaukee to visit the large Milwaukee County Zoo. The accredited zoo is home to over 2,000 animals from more than 300 species and is a great learning experience for families.

Bookworm Garden in Sheboygan is a beautiful, playful botanical garden inspired by popular children's books.

Show Family Playground is a large, well-equipped playground in Sheboygan. This all-inclusive playground has various unique features - great fun for the children of the family.

At the Wisconsin Maritime Museum, you can learn about the maritime history of the Great Lakes region. There are ship models, boats, a WWII submarine, and more to explore at this fascinating museum.

Cedar Crest Ice Cream Factory & Parlor is one landmark destination in Manitowoc. Meet the giant cow standing in front of this popular ice cream parlor, and have a seat outside to enjoy your favorite flavors of ice cream.

Did you know? Sheboygan is dubbed the "Bratwurst Capital of the World," so get ready to enjoy this delicious sausage in all shapes and forms during your visit here.

Things to note: As with other family road trips from Chicago, be aware of possible snowy driving conditions, traffic, and adverse weather if making this road trip in the winter months.

11. Indianapolis

3 hours from Chicago (185 miles)

Why visit Indianapolis with family? Indianapolis is home to well-known sporting events and locations, a range of historic sites and districts, various museums and monuments, and fun attractions.

Indianapolis has a not-too-large, walkable downtown area, and various attractions suitable for the entire family. This makes it a great weekend destination away from Chicago at any time of the year.

Driving to Indianapolis from Chicago: Follow I-94 south out of Chicago and hop onto I-65 to reach Indianapolis.

Our highlights: The Children's Museum of Indianapolis fosters a sense of discovery through its learning experiences and exhibits in that focus on science, arts, and humanities.

Indianapolis Zoo is actually a zoo, an aquarium, and a botanical garden all in one. It is home to over 1,400 animals and nearly 50,000 plants! It is a wondrous place for all the family members to explore.

Visit Rhythm! Discovery Center in downtown Indianapolis; here, you and your children can explore the world's only drum and percussion museum. You may admire historical artifacts or experience and try various hands-on percussion instruments.

If you and your family prefer to spend time outdoors, you can view beautiful nature and interactive art installations at Virginia B. Fairbanks Art & Nature Park.

Did you know? Indianapolis hosts the annual automobile race Indianapolis 500 - the world's largest single-day sporting event. Other well-attended, popular sporting events also take place in the city, one example being another racing event, Brickyard 400.

Things to note: Do check the opening times of Rhythm! Discovery Center, for the attraction, has usually been closed on specific days of the week.

Though Indianapolis doesn't get as much snow as many other long-winter cities, it is still good to be prepared for snowy driving conditions or snowfall during your outings if visiting the city in the winter months.

12. Saugatuck and Grand Rapids

Via benton harbor and south haven.

3 hours 20 minutes from Chicago (185 miles)

Why visit Saugatuck and Grand Rapids with family? This road trip takes you northeast along the shores of Lake Michigan, past lovely small towns and scenic landscapes, to the unique, fascinating cities of Saugatuck and Grand Rapids.

The cities offer much to see and do for children and adults. Saugatuck is known for its award-winning beaches, thriving art scene, and scenic waterways, while Grand Rapids is home to fabulous museums and galleries and also a number of wonderful craft breweries.

Driving to Saugatuck and Grand Rapids from Chicago: You will basically follow the shore of Lake Michigan, heading northeast on this road trip. Take I-90 from Chicago and then switch to I-94 and I-196, which will take you all the way to Saugatuck and Grand Rapids.

Our highlights: Visit Sarett Nature Center in Benton Harbor, where you can walk along meandering nature trails, enjoy observation platforms, participate in nature classes, or admire live animals and a butterfly house.

South Haven Lighthouse, in South Haven on the way, is a beautiful, historic place to take a walk with your family.

You'll find many beaches on your drive up towards Grand Rapids. In Saugatuck, Oval Beach is perhaps the most popular - and historic - beach. White sands and blue waters, nestled in sand dunes and bordered by the Kalamazoo River, present a wonderful opportunity to spend a day out swimming, picnicking, or exploring nature.

Grand Rapids Public Museum offers adventure and fun on three floors. You'll find history and science exhibits here, as well as a historic carousel, a theater, and a planetarium.

Frederik Meijer Gardens & Sculpture Park in Grand Rapids is visited by hundreds of thousands yearly. This botanical garden also has an art museum and an outdoor sculpture park.

Things to note: Winters in these areas of Michigan are known to get very cold, and you might also do well to prepare for possible icy conditions on the roads if making this road trip during the colder season.

13. Wisconsin Dells

3 hours 10 minutes from Chicago (200 miles)

Why visit Wisconsin Dells with family? Wisconsin Dells is a great destination to visit with family. It is especially well known for its many fun and adventurous water parks and for the stunning scenery of forests and gorges to be admired on the Wisconsin River.

Driving to Wisconsin Dells from Chicago: Follow I-90 northwest to Rockford and then to the outskirts of Madison in the north. The interstate will then take you directly to Wisconsin Dells.

Our highlights: About 10 minutes from downtown Wisconsin Dells, Noah's Ark Water Park is one of the largest water parks in the US. Your children (and yourself!) will love the exciting water slides and endless fun to be had at this famous park.

Take a boat tour to view the Dells of the Wisconsin River. These tours leave from the heart of Wisconsin Dells and take you to view mesmerizing glacier-carved gorges and sandstone formations.

Mt. Olympus Water and Theme Park is another fabulous family destination. Inspired by ancient Greece, this theme park has a water park section and a classic theme park section with rides and rollercoasters.

Mirror Lake State Park has wetlands, swimming beaches, trails, and camping facilities. In the summer, you can go boating and canoeing on the lake, and in the winter, skiing and snowshoeing are possible activities.

Did you know? Known as the "Waterpark Capital of the World," Wisconsin Dells a paradise for visitors of all ages. You will find over 20 indoor and outdoor waterparks here during your visit!

Things to note: At Mirror Lake State Park, some of the campsites and facilities are only open during the summer months.

READ MORE - Road Trip from Chicago to Wisconsin Dells

14. Door County

4 hours 30 minutes from Chicago (270 miles)

Why visit Door County with family? For a very scenic road trip, head up north from Chicago to Door County. It is a fabulous weekend or longer vacation destination for the family, with beautiful views, beaches, family-friendly attractions and farmer's markets.

Door County on the Door Peninsula offers spectacular views over Green Bay on one side and Lake Michigan on the other. The area is known for picturesque coastal towns, fruit orchards, lighthouses, and scenic views.

Driving to Door County from Chicago: Head directly north out of Chicago, following the coast of Lake Michigan on I-94 and I-43 until you reach the outskirts of Manitowoc. From here, drive to Green Bay on the interstate and then hop onto WI-54 to reach Door County.

Our highlights: On the shore of Lake Michigan stands Door County's most iconic lighthouse, Cana Island Lighthouse. Explore the island, including the light tower and lighthouse keeper's home.

Peninsula State Park on the shores of Green Bay is a popular camping destination, which is also great for swimming, hiking, biking, or just slowly driving through the park to view the high bluffs and sandy beaches.

The Farm Historic Living Museum in Sturgeon Bay is a great place for children or adults to visit. Here, you can view exhibits on rural farming and heritage and visit farm animals and bottle-feed baby animals in natural farm surroundings.

Don't forget to get on the ferry to cross Death's Door to get onto Washington Island. Children will enjoy the 30-minute ferry ride and explore the island with nature to view, as well as shops and restaurants.

Did you know? Door County is famous for its cherries and is a popular place to go cherry picking. These cherries usually reach their peak ripeness from mid-July to mid-August, when you and your family can experience the joy of picking your own fresh produce.

Things to note: Though Door County is obviously a beautiful, activity-filled summer holiday destination, it is also wonderful in winter. You can do skiing, snowshoeing or ice fishing, and even, if you're lucky, view the northern lights that are often seen here due to less light pollution than elsewhere in Wisconsin.

Just be aware that, although there will always be attempts to keep roads clear during the snowy periods of the winter months, plowing may take some time; it is good to be prepared with proper winter tires and gear if making this road trip in the cold season.

The Farm Historic Living Museum is not open during the months of November until May.

15. Ann Arbor and Detroit

4 hours 30 minutes from Chicago (285 miles)

Why visit Ann Arbor and Detroit with family? This road trip takes you from Chicago by the shores of Lake Michigan to Detroit, on the shores of Lake St. Clair. Museums, amusement parks, outdoor adventures, parks and Detroit Zoo are but some of the examples of child-friendly things to do in this vibrant city.

On the way to Detroit, Ann Arbor is another fabulous place for a stopover; it is especially known for its many interactive, science-focused activities and attractions.

Driving to Ann Arbor and Detroit from Chicago: A road trip from Lake Michigan to Lake St Clair, follow I-94 heading east to reach Ann Arbor. The switch to M-14 and I-96 to arrive at Detroit.

Our highlights: Ann Arbor Hands-On Museum and Leslie Science & Nature Center is a must-see destinations in Ann Arbor for families with children. This museum has engaging, interactive exhibits and activities on various scientific fields and topics.

Detroit Zoo has over 2,000 animals living on its 125 acres of various habitats. The zoo features many award-winning exhibits such as the Wildlife Interpretive Gallery, the Great Apes of Harambee, and the Arctic Ring of Life.

Detroit is known as the automobile capital of the world; Henry Ford built his first car here in 1896, and the city led the manufacturing of cars in this part of the US in the early 20th century. Nowadays, various automobile museums in Detroit are a testimony to this history.

Henry Ford Museum of American Innovation commemorates the life and accomplishments of this famous entrepreneur. The museum features various exhibits on the history of automobiles, and children can take part in interactive games and activities.

Visit Greenfield Village to experience 90 acres of preserved historical buildings, interactive activities, and costumed characters related to Detroit's living history. You can even ride on a horse-drawn carriage or a steam-powered train.

At C.J. Barrymore's play park, you'll find lots of family-friendly fun, from golfing, go-karts, and bowling to thrill rides, video games, and laser tag.

Did you know? Detroit is well known as the birthplace of the distinctive Motown Sound.

Things to note: Be aware of traffic while traveling to Detroit with your family; the large city's streets may experience heavy traffic at times, and conditions can be especially difficult during the snowy winter months. Even Interstate 94, leading to Detroit, can be affected due to snowy or icy conditions during winter.

16. Cincinnati

Via indianapolis.

4 hours 40 minutes from Chicago (300 miles)

Why visit Cincinnati with family? This beautiful riverside city is called "Paris of America" due to its stunning architecture and fantastic museums and theaters.

If you're visiting Cincinnati with your family, some of the fun things to do together include riverfront parks, a zoo, a botanical garden, and museums.

Driving to Cincinnati from Chicago: Head southeast following I-94 and I-65 to reach Indianapolis. From here, switch to I-74 to arrive in Cincinnati.

Our highlights: On the way to Cincinnati, visit the Children's Museum of Indianapolis, the world's largest children's museum. There are over five floors of exhibitions on dinosaurs, space stations and more.

Located on the banks of the Ohio River, Cincinnati is a city known for its arts, world-class breweries, a lovely riverfront, and beautiful 19th-century buildings.

Cincinnati Zoo & Botanical Garden has a large variety of animals, habitats, and gardens to explore. It is dedicated to adventure, education and conservation.

Highfield Discovery Garden at Glenwood Gardens has a variety of activities and adventures for families. There is a fantasy playground where you can explore fairy gardens, a butterfly garden, and trains.

Kings Island is a famous amusement park near Cincinnati. It contains various rides, rollercoasters, water parks, and play areas.

Did you know? Cincinnati is the city where the first concrete skyscraper of the whole world was built; Ingall's Building, finished in 1903. Another first for the city is that the first professional baseball team ever came from here, the Red Stockings of Cincinnati.

Things to note: Take some basic measures to stay safe on the roads if you're making this road trip in winter; have proper winter tires and take it easy in the traffic.

Longer family-friendly trips from Chicago (Over 5 hours each way)

Mid-semester breaks or any other holidays mean having more time to spend with your family! From visiting incredible zoos to admiring world-famous waterfalls, longer road trips from Chicago can be the ultimate family road trip adventure.

17. Sandusky and Cedar Point Amusement Park

Via fort wayne.

5 hours 40 minutes from Chicago (315 miles)

Why visit Sandusky and Cedar Point Amusement Park with family? This road trip first takes you to one of the biggest cities in Indiana, Fort Wayne, where you can visit amazing family attractions such as a children's zoo and a botanical conservatory.

You'll then continue on to the shores of Lake Erie, to beautiful Sandusky, a place with miles of sunny beaches, lovely nature trails, world-class amusement parks, and interesting arts and architecture.

Driving to Sandusky and Cedar Point Amusement Park from Chicago: Head to Fort Wayne from Chicago on US-30 driving southeast. Then hop onto US-24 towards Toledo and switch to I-90 past Waterville. From here, you will drive on OH-4 to reach Sandusky and Cedar Point.

Our highlights: Fort Wayne Children's Zoo is arguably one of the best zoos in the country. Here, you can have close-up experiences with over a thousand animals housed at the zoo.

Cedar Point Amusement Park is located on Lake Erie Peninsula in Sandusky. It is the second-oldest amusement park in the country, operating since 1870.

Less expensive than its counterparts in the larger cities of the US, Cedar Point contains 70 amazing rides, as well as restaurants, hotels, and a waterpark. Please keep in mind that the waterpark has a separate entry.

The Merry-Go-Round Museum in Sandusky contains a historic 1939 Allan Herschell carousel, beautiful historic artifacts and a gift shop, all related to this world-famous, beloved amusement park ride.

Hungry for know knowledge? The Maritime Museum of Sandusky contains exciting exhibits on boats, pirates, and shipwrecks. This is the perfect for any pirate-loving young members of the family to visit.

Pipe Creek Wildlife Area, consisting largely of wetlands, is a beautiful place to do birdwatching and walks in nature. You can enjoy a nice walk here with your family once you have had your fill of all the amazing rides and museums this road trip has to offer.

Did you know? Cedar Point is known as "The Roller Coaster Capital of the World," thrilling for adventure-seekers of all ages!

Things to know: Visiting Cedar Point Amusement Park may turn out cheaper if you book tickets in advance online, rather than buying at the entrance.

18. St Louis

Via peoria and springfield.

5 hours from Chicago (335 miles)

Why visit St Louis with family? St Louis is a fabulous vacation destination for the family, over a long weekend or a longer stay; the city area contains amazing public parks, as well as several free attractions suitable for families with children.

On the way to St Louis, you can stop at Peoria to enjoy the many family-friendly activities here or explore historic sites and attractions in Springfield.

Driving to St Louis from Chicago: Following I-55 southeast of Chicago, use Exit 163 and then 101 to reach Peoria. After your visit, head south on I-155 to Springfield and switch to I-55 to reach St Louis.

Our highlights: On the way to St Louis, Peoria PlayHouse, a children's museum, is worth visiting. It features interactive exhibits on arts, sciences, and music.

Also on the way, you can explore the historic sites of Springfield, including the Abraham Lincoln Presidential Library and Museum. You and your family can learn about history through interactive displays and films.

A must-stop and exciting activity once in St Louis is visiting Gateway Arch. You can ride the tram up to take in views of the Mississippi River and the surrounding city from the top of this 630-foot tall steel structure, or you can visit an interactive museum on site with history exhibitions covering 200 years.

Citygarden Sculpture Park is another lovely destination for a family with children in St Louis. During your visit, you can enjoy beautiful trees and nature, view art displays, and splash in shallow pools and waterfalls. There are food trucks serving food and drinks as well.

Saint Louis Science Center has over 700 interactive exhibits covering various topics. Both children and adults will enjoy a day of exploration and fun at this center. General admission is free; you only pay for certain special exhibits and the IMAX Theater.

Did you know? St Louis is home to many firsts: the first commercial peanut butter was sold here, the first kindergarten in the US was operated in St Louis, and the city was also the birthplace of products such as ice cream cones, 7up, and ice tea.

Things to note: Should you wish to take the tram to the top of Gateway Arch when visiting here, booking tickets in advance is a good idea, as they're often sold out on the busier days.

READ MORE - Road Trip from Chicago to St Louis

19. Cleveland and Cuyahoga Valley National Park

5 hours 50 minutes from Chicago (365 miles)

Why visit Cleveland and Cuyahoga Valley National Park with family? Visit Cleveland with your family to wander through the many city parks and nature areas of this "Forest City", as Cleveland is lovingly nicknamed.

The surroundings of Cleveland, along the shores of Lake Erie, also include beautiful scenic spots and beaches to enjoy.

Driving to Cleveland and Cuyahoga Valley National Park from Chicago: Heading east from Chicago, follow I-90 all the way to Cleveland and then dip south to visit Cuyahoga Valley National Park.

Our highlights: On the way to Cleveland, you can stop at beautiful Toledo by Lake Erie. At the riverfront, you'll find Imagination Station, a hands-on science museum that has over 300 exhibits for children and curious minds to explore.

Cleveland Museum of Art is a truly fascinating and awe-inspiring place, with over 30,000 works of art spanning 5,000 years of history from around the world.

The Rock and Roll Hall of Fame is fun to explore with the whole family. There are interesting artifacts of famous musicians, such as Jimi Hendrix's guitar and John Lennon's bed. Exhibitions with mature themes are marked, which helps if you visit with children.

At the Cleveland Museum of Natural History, you and the family can enjoy fascinating sections such as a dinosaur exhibit, an earthquake simulator, and a live animal wildlife center.

Cuyahoga Valley National Park, close to Cleveland, is home to beautiful landscapes of forests, rolling hills, farmlands and the winding Cuyahoga River. You can explore and learn about the history of the Ohio & Erie Canal or admire the native plants and wildlife.

Did you know? Superman was born in Cleveland! At least in the sense that the creators of the beloved character created the early Superman prototype while still in high school here, in 1933.

Things to note: I-90 from Chicago to Cleveland is generally in great condition. Of course, be aware of traffic during busy periods, and be prepared for snowy conditions if you're doing the road trip in winter.

Though not required, it is best to book tickets in advance online for attractions such as the Rock and Roll Hall of Fame and the Cleveland Museum of Natural History.

READ MORE - Road Trip from Chicago to Cleveland

20. Minneapolis and the Mall of America

6 hours 20 minutes from Chicago (420 miles)

Why visit Minneapolis and the Mall of America with family? This relatively longer road trip from Chicago offers opportunities to visit Madison and Eau Claire on the way. Minneapolis, known for its parks and lakes, is the perfect mix of urban sophistication and natural beauty.

Just walking around the city is an experience in itself; the city is located on the scenic banks of the Mississippi River, and Minneapolis offers both architectural and natural gems to admire.

Driving to Minneapolis and the Mall of America from Chicago: You will be heading northwest on this road trip from Chicago on I-90, which will take you past Madison and Wisconsin Dells before you merge onto I-94. Follow this interstate to reach Minneapolis and the Mall of America.

Our highlights: On the way, you can make a stop at Eau Claire to visit the Children's Museum. It includes imagination-spurring activities and exhibits, such as a construction zone, a miniature city, Water Works, and a Body Parts area.

Walker Art Center in Minneapolis, connected with the Sculpture Garden, contains exhibits of contemporary art. It can be a great way to introduce children to contemporary art, for the center offers activities especially geared towards children.

Minnehaha Park is an old and popular park in Minneapolis. It contains lovely nature trails, and the stunning Minnehaha Falls waterfall is a well-known attraction.

You could easily spend a whole day exploring the Science Museum of Minnesota, located in St Paul, Minneapolis's twin city across the river. It offers four stories of science-related fun, and the interactive exhibits include a news center, "quackery museum," and IMAX theater.

Mall of America is an amazing shopping mall. As one of the biggest shopping malls in the country, it might not be surprising to see more than 500 stores during your visit to the mall!

There are also 50 restaurants and plenty of great activities for the family - the most famous is the Nickelodeon Universe, an indoor amusement park that fits entirely within this enormous mall.

Things to note: If you wish to visit Minneapolis in winter, there is plenty to do, as well as in the summer months; the city's many indoor attractions take care of that.

Just remember to be cautious if traveling on snowy roads during the winter months, and be prepared with proper equipment.

READ MORE - Road Trip from Chicago to Minneapolis

21. Niagara Falls

Via cleveland.

8 hours 30 minutes from Chicago (560 miles)

Why visit Niagara Falls with family? Niagara Falls is a bucket-list destination and is a great place to visit with family. The drive to Niagara Falls from Chicago is lovely as well, with options to stop at diverse cities and nature areas on the shores of Lake Erie.

At Niagara Falls, not only can you visit the world-famous waterfall and view it on a boat tour, but you can also explore beautiful walks, great museums, a waterpark, and a butterfly conservatory in the city.

Driving to Niagara Falls from Chicago: Although this is a longer road trip on our list, it is quite a straightforward drive. Simply follow I-90 from Lake Michigan shores to Lake Erie coastline and head northeast until you reach Cleveland, and then follow this interstate to Buffalo.

From here, head north on I-190 to reach Niagara Falls.

Our highlights: Cleveland is a great stop on the way from Chicago to Niagara Falls. Cleveland Museum of Natural History has exciting exhibits for people of all ages to enjoy, from a dinosaur exhibit to an earthquake simulation and a wildlife center.

A must-see when visiting Niagara Falls is, of course, the famous waterfall. It is said to be best viewed from the Canadian side or from Skylon Tower, so if you have your passports with you, you can see for yourself and decide!

On the USA side, the Maid of the Mist Boat Tour will take you as close as possible to the thundering waterfalls. You'll don a poncho and sail into the heart of the falls, experiencing the mist, roar, and sheer power of Niagara Falls. Please note that these tours can be seasonal and check before visiting.

Cave of the Winds Tour will take you to the base of the Bridal Veil Falls, where you can explore the wooden walkways just a few feet away from the cascading water. The highlight is the "Hurricane Deck," where you can experience tropical storm-like conditions.

On the Canadian side, the Skylon Tower is a 764-foot-tall observation tower with an arcade and a revolving restaurant. It offers magnificent views of the waterfall and the surrounding city.

While in Canada, you can also visit the Niagara Butterfly Conservatory. Wander through this tropical paradise and view its plants, flowers, and over 2,000 butterflies. You can watch an introductory video and take your time to meander through the garden.

Did you know? Beyond its breathtaking natural beauty, it's also known for daredevil stunts, like tightrope walks across the falls.

Things to note: Niagara Falls waterfall can be magical to view in winter as well! Then, parts of the falls freeze over, and special light displays further increase the enchantment of the falls.

Though not absolutely necessary, booking tickets to Skylon Tower in advance is recommended.

READ MORE - Road Trip from Chicago to Niagara Falls

22. Dollywood, Gatlinburg and Great Smoky Mountains National Park

Via louisville.

9 hours 20 minutes from Chicago (590 miles)

Why visit Dollywood, Gatlinburg and Great Smoky Mountains National Park with family? This scenic road trip will take you south from Chicago, through the states of Indiana and Kentucky, into Tennessee and the Great Smoky Mountains National Park.

he national park is full of stunning trails, viewpoints, and picnic spots. Gatlinburg is an attraction-filled mountain town and a gateway to the nearby national park. You can also visit the Dollywood theme park for fun and thrilling experiences on the way.

Driving to Dollywood, Gatlinburg and Great Smoky Mountains National Park from Chicago: Heading out of Chicago on this longer drive, use I-94 and then I-65 to drive through Indianapolis and then Louisville. Switch to I-75 past Lexington to arrive at your destination in Knoxville.

After your visit, follow I-40 to Dollywood and then Gatlinburg, your gateway to the beautiful Great Smoky Mountains National Park.

Our highlights: In Louisville, there are many unique attractions to visit. These include the Kentucky Derby Museum and Louisville Mega Cavern, where you can enjoy fully underground aerial rope challenges, ziplines, and adventure tours.

Dollywood, owned by Dolly Parton, is full of enchanting attractions, from rollercoaster rides and waterparks to children's playgrounds and country restaurants. What better way to start your family road trip?

Be ready to be astonished at Ripley's Aquarium of the Smokies in Gatlinburg, where you can admire over 10,000 exotic sea creatures spread over ten themed galleries.

Ober Mountain is another fantastic place to visit in Gatlinburg. This mountainside amusement park offers minigolf, wildlife encounters, and hiking in summer, and skiing and snowboarding in winter, and you can enjoy stunning views over the Great Smoky Mountains National Park any season of the year.

Great Smoky Mountains National Park is a vast, beautiful area to explore. Take a picnic in the forest, view wildlife, and explore the rivers and waterfalls. It will be an experience to remember for the entire family.

Did you know? While exploring the Great Smoky Mountains, you may encounter a diverse range of wildlife: there are over 4,000 plants, 65 species of mammals, 200 species of birds, nearly 70 species of fish, and over 80 species of reptiles and amphibians that call this region home.

The national park is also called the "Salamander capital of the world," for the park is home to 30 different species of salamander!

Things to note: Great Smoky Mountains National Park is open year-round, although certain visitor facilities will be closed in winter.

Be extra careful and prepared with the correct equipment on the mountainous roads of this region if making this road trip in winter.

23. Orlando

Via atlanta.

18 hours from Chicago (1,160 miles)

Why visit Orlando with family? This epic, longer road trip from Chicago is the perfect one to do with older children and will take you south through various states, past several buzzing metropolises into sunny Florida and Orlando, a theme park capital of the world.

Take your time with the family to stop at the various cities and nature areas along the way. Enjoy the landscapes of rolling hills around Louisville and the forests of Tennessee and Georgia, and visit the various attractions in cities such as Nashville and Atlanta.

In Orlando, you can spend days and days exploring the various theme parks around the city, the most famous of which are perhaps Walt Disney World Resort, Universal Orlando, and Legoland.

Driving to Orlando from Chicago: The road trip from Chicago to Orlando is the longest on our list, but it is fairly easy to follow as most of the driving will take place on the interstates.

From Chicago, head south through Indianapolis and Louisville on I-65 until you reach Nashville. From here, hop onto I-24 and then I-75 past Chattanooga. This interstate will take you all the way into Florida, Florida's Turnpike will then take you to Orlando.

Our highlights: Atlanta is one of the many amazing places to stop on this road trip. In Atlanta, we recommend visiting the stunning Atlanta Botanical Garden. It is a world of magic and beauty, with unique plant centers, features, and gardens.

Walt Disney World Resort is one of the most popular attractions in Orlando. This entertainment resort complex is a world of magic and fun, home to four theme parks and two water parks.

Universal Orlando also has famous attractions, rides, and live shows. Our favorite places to visit here with family are the Wizarding World of Harry Potter and the Minions section, but maybe you will discover a new favorite!

Did you know? Did you know that Walt Disney World Resort is about the same size as San Francisco? This vast theme park is Florida's most popular tourist destination, attracting almost 60 million people every year. The park offers something to everyone, whatever your age or background!

Things to note: It is a good idea to book tickets to Orlando theme parks in advance to avoid any disappointments or waiting times.

READ MORE - Road Trip from Chicago to Orlando

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6 Best Road Trips From Chicago

Waterfalls, storybook towns, incredible food, and more await just a short drive from Chicago.

Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception.

Fortunately, there's a whole world out there beyond the city limits. While it doesn't always feel like it, there are so, so, so many worthy escapes within a few hours' drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City's location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You're within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

Madison, Wisconsin

Imagine a state already known for its beer and cheese having to cater to over 30,000 college students, and you've got some idea of the earthly delights that await in Madison, Wisconsin. This state capital could have been a destination in its own right for its unique geography — located on a narrow isthmus surrounded by two large lakes, it's beautiful even during cold Wisconsin winters — or its remarkable breadth of shopping, cultural events, and festivals, and architecture, but its food scene is virtually unrivaled for a city of its size.

The streets are filled with an eclectic mix of professors, politicians, businesspeople, street performers, and health nuts, and if you ask any of them for their favorite spot, you'll likely get a range of answers as large as the city's 250,000-plus population: American small bites at the new and renowned Mint Mark, tacos and margaritas at Canteen, Lao-Thai noodles from Vientiane Palace, and the list goes on and on.

Most students, however, will drive you toward craft-beer watering holes like The Malt House or Dotty Dumpling's Dowry, which purportedly serves one of the best burgers anywhere. Wash it down with some Wisconsin beer from New Glarus as well as some fried cheese curds, and you'll have yourself a real Madison, Wisconsin, night.

Madison is about two and a half hours from Chicago.

Starved Rock State Park, Illinois

Yes, Illinois isn't known for its natural beauty like some other states. Yes, its highest natural point is Charles Mound, a diminutive 1,235-foot hill. But that doesn't mean that hidden gems don't exist here. For a true escape from Chicago's steel-and-stone skyscrapers that is still within the state limits, drive to the area around Starved Rock State Park.

Visitors expecting more flat Illinois farmland will be surprised to find an incredible valley around the Illinois River, with lush trees, striking bluffs, and 14 gorgeous waterfalls feeding into the roaring waters. Starved Rock is a choice destination for camping, hiking, kayaking, and white-water rafting, and after you're exhausted from a day of physical exertion, it's also got a place to hang your hat: the Starved Rock Lodge .

However, if you feel like experiencing a bit more of the local flavor, the towns around the river valley provide it in buckets. Tiny, charming Utica is home to the August Hill Winery and some wonderful antique stores, while the historic towns of Oglesby and Ottawa are chock-full of Americana: small museums, galleries, and great food, particularly at the Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.

Starved Rock State Park is about an hour and a half from Chicago.

Allegan County, Michigan

Lake Michigan is huge. And in the summertime, when the heat gets a little unbearable, you could easily just jump into the lake in Chicago. But there's something to be said for taking a jaunt out to Michigan to visit a string of lakeside towns that bring some truly unique qualities to the mix.

Douglas, Saugatuck, and Holland — and Fennville, though it's not right on the water — epitomize small-town charm, while still offering some truly city-sized amenities for city-sized appetites. Fennville is known as the fruit basket of Michigan, with apple orchards, vineyards, and berry farms alongside delightful creameries and even corn mazes, while Saugatuck and Douglas consistently take the cake as two of the best lakeside towns in the Midwest, with incredibly charming downtown areas, gorgeous undulating sand dunes, pristine blue water, and more art galleries than you can shake a stick at. In fact, it's here that two School of the Art Institute of Chicago instructors founded their own art school and residence, Ox-Bow, establishing an artists' colony right on the shores of Lake Michigan. Their legacy endures to this day.

Further up the road, you'll find a truly unique destination in Holland, where Dutch colonists established a foothold in the 1800s, bringing with them their culture, architecture, pastries (check out DeBoer Bakkerij), and even fields' worth of tulips, which you can find at Veldheer Tulip Gardens.

Fennville is about two hours from Chicago.

Everything You Need to Know Before Renting an RV for the First Time

Indianapolis, indiana.

Among the many types of travelers out there — people who crave solitude, people who don't want to leave the 100-foot radius of their resort's pool — there are those who are fascinated by city life, jumping from one urban area to another. If you count yourself among them, a road trip from Chicago to Indianapolis is certainly warranted.

First off, it's the 15th-largest city in America, with a vast population and penchant for festivals, parties, and overall pageantry (it is the Racing Capital of the World, after all, and its famous month of May includes tons of smaller celebrations leading up to the Indy 500). No matter the time of year, though, you'll find Indianapolis in full swing, whether you're in the midst of its rollicking IndyFringe Festival in August and September or its Wine & Food Festival in June. It's also a museum hub, with the world's largest children's museum, several art museums with broad and granular focuses, and small museums focusing on its favorite children, from Vonnegut to President Benjamin Harrison.

But one of the main reasons visitors flock to Indianapolis is its incredible food scene, which has, in recent years, exploded into national prominence. Hot new restaurants like Bluebeard, Milktooth, Crispy Bird, Oca, and more have all contributed to its reputation as a gastronomical powerhouse, while iconic institutions like Workingman's Friend have been, well, working behind the scenes to keep Hoosiers well-fed for decades. It's about time their city gets noticed.

Indianapolis is about three hours from Chicago.

Traverse City, Michigan

If you're craving a real getaway, you can't do much better than northern Michigan — it's still within driving distance of Chicago and not as remote as the state's Upper Peninsula, while still providing a wilderness-tinged escape for city dwellers. The de-facto capital of the region, Traverse City, is a city in name, but its population of around 15,000 means it's got small-town charm and accessibility, making it a perfect gateway to the region's breathtaking sights. Stop in for a glass of beer or wine at one of the many famous wineries and brewpubs, like Mari Vineyards or Mackinaw Brewing Company, before heading into the wilderness.

From Traverse City's quaint streets, you can head north and explore the Leelanau Peninsula, or veer west to Sleeping Bear Dunes National Lakeshore. Better yet, take scenic M-22 to tick off both boxes. Sleeping Bear Dunes is one of the country's best stretches of shoreline, with incredible dunes and westerly views that mean it's got some of the best sunsets east of the Mississippi.

From there, mosey up M-22 to continue exploring the Leelanau Peninsula, where wilderness encroaches a bit further and small towns, each with a population under 1,000, dot the roads. Hike through the dense forests, pick apples and berries at the region's many farms, and be sure to grab a heaping sandwich from the Village Cheese Shanty in the county seat of Leland (population 377).

Traverse City is about five hours from Chicago.

Galena, Illinois

In rare cases, a road trip doesn't just mean traveling great distances — it can also mean traveling back in time. That's what's figuratively the case when you drive west from Chicago to Galena, consistently rated as one of the best small towns in America. For decades, Galena has been on a mission to preserve its rich history, meaning it has one of the most unspoiled historic town centers in the country.

The town's good fortune started back in the mid-1800s, when it was the beneficiary of government grants to begin mining precious minerals located under the town. Since then, the town has focused on maintaining the buildings from that boom time, and there are architectural landmarks around every corner. The Galena Historic District is a particular delight, comprising more than 1,000 buildings, including the home of Ulysses S. Grant, a prime example of the Italianate style and now a dedicated memorial to his legacy. The town even has trolley tours that take you to its major historical and architectural benchmarks, contributing to its overall throwback feel.

Galena's best eating institutions don't necessarily date all the way back to 1850, but that doesn't mean they aren't also great — Durty Gurt's Burger Joynt was founded in 2007 and serves gigantic, almost architecturally impressive stacks of meat and cheese. Looks like everyone's concerned with building a legacy here.

Galena is about three hours from Chicago.

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15 Ultimate Road Trips from Chicago

Table of Contents

Key Highlights

• Explore the natural beauty of Starved Rock State Park and enjoy hiking and waterfalls
• Visit the stunning Indiana Dunes National Park and spend a day on the sandy beaches
• Discover the charming town of Galena, Illinois with its rolling hills and historic charm
• Relax in the resort town of Saugatuck, Michigan and explore its art galleries and beautiful Oval Beach
• Experience the vibrant art scene in Milwaukee, Wisconsin and enjoy views of Lake Michigan

Introduction

Chicago , the Windy City , is a bustling metropolis filled with skyscrapers, world-class museums, and a vibrant culture. But sometimes, you need to escape the city and hit the open road for a memorable adventure. Luckily, Chicago is surrounded by numerous road trip destinations that offer stunning natural beauty, charming towns, and unique attractions. Whether you’re looking for a day trip or a weekend getaway, there are plenty of options within a few hours’ drive of Chicago.

From the picturesque shores of Lake Michigan to the rolling hills of Illinois and the vibrant cities of Wisconsin and Michigan, there’s something for everyone in this list of ultimate road trips from Chicago. So pack your bags, fill up the tank, and get ready to embark on an unforgettable road trip adventure from the Windy City.

Ready For the Best Road Trips from Chicago?

Many exciting road trips from Chicago are under three hours away and explore diverse destinations rich with natural wonders and cultural experiences. Traverse to Starved Rock State Park in Illinois for majestic canyons and waterfalls, or head to Indiana Dunes National Park for sandy shorelines along Lake Michigan. Discover the charm of Lake Geneva in Wisconsin or the historic town of Galena in Illinois, each offering a unique escape. Experience the artsy vibes of Saugatuck in Michigan or the vibrant city of Milwaukee in Wisconsin. Nearby gems like Madison and Door County in Wisconsin promise scenic beauty and outdoor adventures, perfect for a quick getaway.

15 Top Road Trips from Chicago

Chicago is the perfect starting point for exciting road trips. Whether you’re looking for natural beauty, historical sites, or vibrant cities, there’s a road trip for everyone. From the stunning Starved Rock State Park in Illinois to the picturesque Door County in Wisconsin, there are endless options to explore. Take a drive to the charming town of Galena, Illinois, known for its rolling hills and historic charm. Or head north to Saugatuck, Michigan, a resort town with art galleries and a beautiful beach. Don’t forget to visit Milwaukee, Wisconsin, and discover its vibrant art scene and views of Lake Michigan. With so many options, the road trips from Chicago are sure to provide unforgettable experiences.

Make your reservation so you will not be locked out of any lodging. So many people enjoy road trips from Chicago!

1. Starved Rock State Park, Illinois

Located just a short drive from Chicago, Starved Rock State Park is a nature lover’s paradise. With its towering canyons, cascading waterfalls, and breathtaking views of the Illinois River, it’s no wonder this park is a popular destination for day trips. Hike the trails that wind through the park and take in the stunning vistas from the top of Starved Rock, a sandstone butte that rises 125 feet above the river. Don’t miss the park’s waterfalls, including the iconic LaSalle Canyon waterfall, which can be seen from a boardwalk trail.

With its abundant wildlife, scenic overlooks, and picnic areas, Starved Rock State Park is the perfect place to escape the hustle and bustle of the city and reconnect with nature.

2. Indiana Dunes National Park, Indiana

Just a short drive from Chicago, Indiana Dunes National Park offers a unique combination of sandy beaches, towering sand dunes, and diverse ecosystems. Explore the park’s 15,000 acres of preserved land, where you can hike through forests, paddle along the shoreline, and admire the stunning views of Lake Michigan. Don’t miss the opportunity to climb the 125-foot-tall Mount Baldy, one of the park’s most iconic sand dunes.

Or relax on the beautiful beaches and soak up the sun. With its diverse range of activities and natural beauty, Indiana Dunes National Park is a must-visit destination for nature lovers and outdoor enthusiasts.

3. Lake Geneva, Wisconsin

If you’re looking for a family-friendly road trip destination near Chicago, look no further than Lake Geneva, Wisconsin . This charming resort town offers a wide range of activities for all ages.

Spend the day at one of the area’s water parks, like Timber Ridge Lodge and Waterpark or the indoor water park at Grand Geneva Resort. If you’re looking for a family-friendly road trip destination near Chicago, look no further than Lake Geneva, Wisconsin . This charming resort town offers a wide range of activities for all ages. Spend the day at one of the area’s water parks, like Timber Ridge Lodge and Waterpark or the indoor water park at Grand Geneva Resort. Enjoy outdoor activities like boating, fishing, and hiking along the scenic lakeshore. Take a stroll through the town’s historic district, filled with unique shops and restaurants. And don’t forget to indulge in some delicious ice cream at one of the local ice cream parlors. With its beautiful lake views and endless outdoor adventures, Lake Geneva is the perfect destination for a fun-filled road trip.

4. Galena, Illinois

Escape the hustle and bustle of the city and take a road trip to Galena, Illinois . This charming small town is nestled among rolling hills and offers a glimpse into the past with its well-preserved 19th-century architecture. Take a stroll down Main Street and explore the town’s unique shops, art galleries, and antique stores.

Visit the Ulysses S. Grant Home State Historic Site and learn about the life and presidency of the Civil War general and 18th President of the United States.

The Great Galena Balloon Race is a do not miss adventure. Take a scenic drive along the Galena River and enjoy the stunning views of the surrounding countryside. With its historic charm and natural beauty, Galena is the perfect destination for a relaxing road trip.

5. Saugatuck, Michigan

For a road trip that combines art, nature, and a charming resort town, head to Saugatuck, Michigan . This picturesque town is known for its vibrant art scene, beautiful beaches, and quaint downtown area. Explore the many art galleries and studios, where you can find unique pieces of artwork created by local artists. Spend the day at Oval Beach, one of the most beautiful beaches in the Midwest, and soak up the sun or take a dip in Lake Michigan.

Take a stroll through the downtown area and browse the boutiques, shops, and restaurants. With its combination of art, nature, and small-town charm, Saugatuck is the perfect destination for a road trip getaway.

6. Milwaukee, Wisconsin

Just a short drive north of Chicago, Milwaukee offers a unique combination of art, culture, and scenic views of Lake Michigan . Start your visit with a trip to the Milwaukee Art Museum, known for its stunning architecture and impressive collection of artwork. Explore the city’s vibrant public art scene, with murals and sculptures scattered throughout the downtown area. Take a stroll along the lakefront and enjoy the panoramic views of Lake Michigan. Don’t miss the chance to visit the Harley-Davidson Museum and learn about the history and culture of this iconic American motorcycle brand. With its diverse range of attractions and beautiful lake views, Milwaukee is a road trip destination that is sure to captivate visitors of all ages.

7. Madison, Wisconsin

The capital city of Wisconsin, Madison , offers a blend of natural beauty, vibrant culture, and a thriving food scene. Start your visit with a trip to the beautiful Olbrich Botanical Gardens, where you can explore stunning gardens and enjoy the peaceful atmosphere. Take a stroll through the University of Wisconsin-Madison campus and admire the historic buildings and lush green spaces. Visit the Wisconsin State Capitol and take a guided tour to learn about the history and architecture of this iconic building.

Don’t miss the chance to explore the nearby Devil’s Lake State Park , a local favorite for hiking, swimming, and picnicking. With its combination of natural beauty and cultural attractions, Madison is a road trip destination that is sure to please.

8. Door County, Wisconsin

Located on a picturesque peninsula between Green Bay and Lake Michigan, Door County is a popular road trip destination known for its stunning natural beauty and outdoor activities. Explore the numerous state parks and nature preserves, where you can hike, bike, or kayak through pristine forests and along scenic shorelines. Take a scenic drive along the Door County Coastal Byway and enjoy the panoramic views of the lake and countryside.

Visit the charming towns of Fish Creek, Ephraim, and Sister Bay , where you can browse art galleries, shop for unique souvenirs, and indulge in delicious local cuisine. With its idyllic landscapes and charming small towns, Door County is the perfect destination for a relaxing and scenic road trip.

9. Holland, Michigan

For a road trip that combines Dutch heritage and beautiful flowers, head to Holland, Michigan. Known for its vibrant tulip fields and annual Tulip Time Festival , Holland is a must-visit destination for flower and culture lovers. Explore the stunning tulip gardens at Windmill Island Gardens , where you can admire thousands of colorful blooms and learn about Dutch culture and history.

Visit the DeZwaan Windmill , the only authentic Dutch windmill in the United States, and take a guided tour to learn about its history and operation. Don’t miss the chance to explore the charming downtown area, with its unique shops, restaurants, and art galleries. With its Dutch heritage and beautiful flowers, Holland is a road trip destination that is sure to delight visitors of all ages.

10. Springfield, Illinois

For history buffs, a road trip to Springfield, Illinois is a must. This capital city is known for its rich history and association with Abraham Lincoln, the 16th President of the United States. Visit the Abraham Lincoln Presidential Library and Museum , where you can learn about Lincoln’s life and legacy through exhibits and interactive displays. Explore the Lincoln Home National Historic Site, where you can tour the only home that Lincoln ever owned. Don’t miss the chance to visit the Old State Capitol, where Lincoln delivered his famous “House Divided” speech. With its historic sites and connection to Abraham Lincoln, Springfield is a road trip destination that offers a fascinating journey into the past.

11. Cedarburg, Wisconsin

Step back in time and visit the charming town of Cedarburg, Wisconsin. With its well-preserved historic buildings and small-town charm, Cedarburg offers a unique road trip experience. Take a stroll down Washington Avenue and admire the beautiful 19th-century architecture.

Browse the numerous shops, art galleries, and antique stores that line the streets. Don’t miss the chance to visit the Cedar Creek Settlement , a collection of historic buildings that now house shops, cafes, and art studios. Enjoy a meal at one of the town’s restaurants, many of which offer outdoor dining options. With its historic charm and small-town feel, Cedarburg is the perfect destination for a peaceful and nostalgic road trip.

12. Michigan City, Indiana

Located on the shores of Lake Michigan , Michigan City, Indiana offers a delightful beach getaway just a short drive from Chicago. Spend the day at the picturesque Washington Park Beach, where you can relax on the sandy shores and swim in the clear waters of Lake Michigan. Visit the historic Michigan City Lighthouse and take in the panoramic views of the lake and the city.

Located on the shores of Lake Michigan , Michigan City, Indiana offers a delightful beach getaway just a short drive from Chicago. Spend the day at the picturesque Washington Park Beach, where you can relax on the sandy shores and swim in the clear waters of Lake Michigan. Visit the historic Michigan City Lighthouse and take in the panoramic views of the lake and the city. Explore the nearby Indiana Dunes National Park and hike along the sandy trails or go birdwatching in the wetlands. Don’t miss the chance to visit the Blue Chip Casino and try your luck at the slot machines or enjoy a delicious meal at one of the many restaurants. With its beautiful beaches and leisurely atmosphere, Michigan City is the perfect destination for a relaxing and fun-filled road trip.

13. Elkhart Lake, Wisconsin

For a road trip destination that combines adrenaline-pumping road racing and lake fun, head to Elkhart Lake, Wisconsin . This small town is known for its historic road racing circuit, Road America, where you can watch thrilling races or even participate in a driving experience. Spend the day at the beautiful Elkhart Lake, where you can swim, kayak, or paddleboard on the crystal-clear waters. Enjoy a picnic on the lakefront or rent a boat and explore the lake at your own pace. Don’t miss the chance to visit the Osthoff Resort , a luxury resort located on the shores of Elkhart Lake, where you can relax in the spa or enjoy a delicious meal with lake views. With its unique combination of road racing and lake activities, Elkhart Lake is the perfect destination for a road trip that offers something for everyone.

14. Shawnee National Forest, Illinois

Escape to the natural wonders of Shawnee National Forest in southern Illinois. This vast forest offers a variety of outdoor activities and stunning natural beauty. Hike through the forest and marvel at the unique rock formations, including the iconic Garden of the Gods, where massive sandstone cliffs rise above the surrounding landscape. Explore the numerous trails that wind through the forest, leading to hidden waterfalls and breathtaking vistas.

Don’t miss the chance to visit the Shawnee Wine Trail , where you can sample local wines and enjoy the scenic views of the vineyards. With its natural wonders and outdoor adventures, Shawnee National Forest is the perfect destination for a road trip that immerses you in the beauty of nature.

15. Ottawa, Illinois

Located in southern Illinois, Ottawa is a charming town that offers a variety of attractions and outdoor activities. It is located close to the historic Starved Rock Lodge and the nearby Starved Rock State Park , known for its stunning canyons and waterfalls. Take a scenic drive along the Illinois River Road and enjoy the beautiful views of the river and surrounding countryside. Explore the quaint downtown area, with its unique shops, art galleries, and restaurants. Don’t miss the chance to visit the Illinois Waterway Visitor Center and learn about the history and importance of the Illinois Waterway. With its natural beauty and small-town charm, Ottawa is the perfect destination for a road trip that takes you off the beaten path and into the heart of southern Illinois.

Planning Your Road Trip from Chicago

Planning a road trip from Chicago requires some careful preparation to ensure a smooth and enjoyable journey. Here are some essential tips to keep in mind:

• Plan your route and make a list of must-visit destinations along the way
• Check the weather forecast and pack accordingly
• Make sure your vehicle is in good condition and fill up on gas before you hit the road
• Research accommodations and make reservations in advance
• Pack snacks, drinks, and entertainment for the drive
• Check for any road closures or construction updates before you leave
• Have a backup plan in case of unexpected detours or delays

Essential Tips for a Smooth Journey

• Research the best places to visit and plan your itinerary accordingly
• Pack light and bring only essential items
• Check the local weather forecast and pack appropriate clothing
• Make sure your vehicle is in good condition and has been serviced before the trip
• Take breaks and stretch your legs during long drives
• Bring a GPS or map to navigate unfamiliar routes
• Pack snacks, water, and entertainment to keep yourself and your passengers occupied during the drive

Best Times of the Year to Travel

The best time of year to take a road trip from Chicago depends on your preferences and the destinations you plan to visit. Summer is a popular time to travel, as the weather is warm and many attractions are open. This is especially true for destinations like Six Flags Great America and the Wisconsin Dells , known as the Waterpark Capital of the World. Spring and fall offer milder weather and fewer crowds, making them ideal for outdoor activities and exploring nature. Winter can be a great time to visit if you enjoy winter sports or holiday festivities. Consider the weather conditions, peak seasons, off-season discounts, and travel costs when planning your road trip from Chicago.

What to Pack for Your Road Trips from Chicago

Packing for a road trip from Chicago requires some careful planning to ensure you have everything you need for a comfortable and enjoyable journey. Here are some essentials to consider packing:

• Comfortable clothing and shoes for different weather conditions
• Toiletries and personal care items
• Snacks, drinks, and a cooler to keep them fresh
• Entertainment options such as books, games, and music
• Roadside emergency kit and first aid supplies
• Maps or a GPS device for navigation
• Chargers for electronic devices
• Extra blankets and pillows for comfort during rest stops
• Travel documents, including identification and insurance information

Road Trip Necessities

• Comfortable clothing and shoes for walking and outdoor activities
• Sunscreen and insect repellent for protection from the elements
• Water bottles to stay hydrated during the drive
• Snacks and a cooler to keep them fresh
• Cash and credit cards for expenses along the way
• A camera to capture the memories
• A road atlas or GPS device for navigation
• A first aid kit for any minor injuries or illnesses
• A portable phone charger for emergencies

Entertainment for the Drive

• Create a road trip playlist with your favorite songs and artists
• Download podcasts or audiobooks for a more immersive experience
• Play car games like “I Spy” or trivia to keep everyone engaged
• Bring along a portable DVD player or tablet for movies or TV shows
• Have a selection of books or magazines for reading during rest stops
• Pack a deck of cards or other portable games for some friendly competition
• Use apps like Spotify or Pandora to discover new music or podcasts
• Prepare a list of podcasts or educational audio programs to learn something new during the drive
• Take advantage of the scenery by playing “Road Trip Bingo” or other observation games
• Make a travel journal or scrapbook to document the trip

Staying Safe on the Road Trips from Chicago

Safety should always be a top priority. Here are some tips to ensure a safe and enjoyable journey when taking road trips from Chicago:

• Always wear your seatbelt and ensure all passengers are properly restrained
• Avoid distractions while driving, such as using your phone or eating
• Take regular breaks to rest and stretch your legs
• Keep a safe following distance from other vehicles
• Be prepared for emergencies with a roadside emergency kit and a first aid kit
• Stay alert and aware of your surroundings
• Follow the rules of the road and be respectful of other drivers
• Monitor weather conditions and adjust your driving accordingly

What to Do in Case of an Emergency

In case of an emergency during your road trip from Chicago, it’s important to be prepared and know what to do. Here are some steps to take in different emergency situations:

It’s always a good idea to have emergency numbers saved in your phone and carry a first aid kit in case of minor injuries.

Embark on unforgettable road trips from Chicago to discover hidden gems and natural wonders within a few hours’ drive. From the majestic Starved Rock State Park to the serene Lake Geneva, each destination promises unique experiences. Plan your journey with essential tips for a safe and enjoyable adventure, ensuring you’re well-prepared and informed. Whether you prefer a solo escapade or a budget-friendly group expedition, these road trips offer something for everyone. Pack your bags, hit the road, and create lasting memories on these ultimate routes from the bustling city of Chicago.

Frequently Asked Questions

What is the best time of year to take a road trip from chicago.

The best time of year to take a road trip from Chicago depends on your preferences and the destinations you plan to visit. Summer offers warm weather and many attractions are open, while spring and fall offer milder weather and fewer crowds.

How do I plan my route for a road trip from Chicago?

To plan your route for a road trip from Chicago, use a GPS or online mapping tool to determine the best route. Consider scenic routes and plan for rest stops along the way to break up the drive.

Are there any hidden gems close to Chicago for road trippers?

Yes, there are several hidden gems close to Chicago for road trippers. Consider visiting lesser-known destinations like Cedarburg, Wisconsin, or Ottawa, Illinois, for a unique and off-the-beaten-path experience.

What should I pack for a road trip during winter?

For a road trip during winter, pack warm clothing, including hats, gloves, and boots. Prepare your vehicle by checking the battery, tire pressure, and fluid levels. Carry a snowbrush and ice scraper for clearing your windows.

How can I make my road trip from Chicago more enjoyable?

To make your road trip from Chicago more enjoyable, bring along entertainment like travel games or audiobooks, pack snacks and drinks, and create a music playlist with your favorite songs.

Can I complete a road trip from Chicago on a budget?

Yes, it is possible to complete a road trip from Chicago on a budget. Look for cost-saving tips like packing your own meals, staying in affordable accommodations, and choosing free or low-cost activities.

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10 Best Weekend Road Trips From Chicago, Illinois

Posted by Brittany Varano June 01, 2021 Updated May 21, 2024

Sometimes you need a change of scenery, and these weekend road trips from Chicago make it easy to get away from the bustle of the Windy City.

Perfectly perched within reach to four different states, Chicago conveniently sits at the crossroads to destinations in Wisconsin, Michigan, Indiana, Iowa, as well as the rest of Illinois.

Its prime location means endless weekend road trips that range from city escapes to small-town excursions and outdoor getaways. And you’ll have your choice of several sandy beach towns lining the shores of neighboring Lake Michigan.

Below, you’ll find a diverse list of the best weekend road trips from Chicago to inspire your next adventure out of the city.

Related Read: The 10 Best Illinois Glamping Rentals

1. Milwaukee, Wisconsin

Milwaukee is an easy weekend trip just north of Chicago over the Wisconsin border. Known for its craft breweries and local eats, there’s a lot to do and see in this smaller midwestern city. If you’re interested in learning about the local history, make time to visit Milwaukee’s beloved museums like the historic art museum or the Harley Davidson Museum to marvel at one of Elvis Presley’s classic motorcycles.

If you’re a sports fan, make time to catch a Milwaukee Bucks basketball game or tailgate outside of Miller Park before watching the Brewers play ball. The end of summer is also a fantastic time to visit Milwaukee as Summerfest is in full swing. Summerfest is a music festival held along the picturesque shores of Lake Michigan in downtown Milwaukee and brings notable acts each year.

Distance from Chicago: 93 miles (approx. 1 hour and 30 minutes)

Related Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway

2. Starved Rock State Park

If peace in nature is what you’re seeking, Illinois’ Starved Rock State Park is a beautiful outdoor getaway known for scenic sandstone canyons, numerous waterfalls, and miles of hiking trails. The park’s top sights include Lover’s Leap Overlook (a lookout point offering clear views of the Starved Rock Dam) as well as the Wildcat, French, and St. Louis canyons.

Summertime is the best time to visit, bringing sunshine and warm weather. Winter is also not a bad time to visit, when the canyon falls freeze over in a spectacular show of ice and snow. Many visitors opt to camp out in the state campground, where reservations can be made up to six months in advance. The park is on the Illinois River southwest of Chicago.

Distance from Chicago: 94 miles (approx. 1 hour and 30 minutes)

Related Read:   9 Fabulously Unique Places to Stay in Illinois

3. Indianapolis, Indiana

Indianapolis is an excellent weekend road trip from Chicago for city dwellers and racing fans. Home to the world-famous Indy 500 and the Indianapolis Motor Speedway Museum , car lovers can cheer on their favorite drivers and learn a bit about the sport’s history.

No visit to Indy is complete without sampling some local cuisine, including local specialities like pork tenderloin sandwiches and shrimp cocktail. The city was named as an ‘Underrated Food City in America’ by Condé Nast Traveler for its rich and diverse restaurants and dishes. Other popular things to do in Indianapolis include walking the eight-mile Indianapolis Cultural Trail that stretches through downtown or visiting the iconic Monument Circle.

Distance from Chicago: 184 miles (approx. 3 hours)

Related Read:   10 Romantic Getaways Near Chicago, Illinois

4. Galena, Illinois

For a taste of small-town living, look to Galena, Illinois . The city has consistently been ranked as one of America’s most livable cities and offers a lovely weekend trip from the big city. Galena is known for its quaint main street lined with historic brick buildings dating to the 1800s.

Visitors can tour the former home of Ulysses S. Grant and visit the beautiful grounds of the Dowling House, the oldest home in the city. Rolling hills and Native American effigy mounds surround Galena, such as the Horseshoe Mound, a nature preserve boasting views of three nearby states. The best way to experience Galena is to stay in a charming bed and breakfast or a local vacation rental.

Distance from Chicago: 164 miles (approx. 2 hours and 45 minutes)

5. Indiana Dunes National Park

Boasting the shortest distance of all the road trips from Chicago, the Indiana Dunes National Park is a convenient road trip from Chicago to northwestern Indiana. The park protects over 15,000 acres of diverse landscapes that include sunny beaches, sand dunes, wetlands, and forests.

The park is a four-season destination offering wildflowers in the spring, water fun in the summer, fiery colors as the leave change in the fall (and sunsets are great), and cross-country skiing in the winter.

Most people opt to camp out in the national park campground or stay in nearby vacation rentals. Besides the outdoor adventures inside the park, make time to shop at the Saturday European Market in Chesterton, visit the Old Lighthouse Museum , and indulge in Indiana comfort food.

Distance from Chicago: 49 miles (approx. 56 minutes)

6. Grand Rapids, Michigan

Get a feel for Michigan city life with a weekend in Grand Rapids . About three hours north of Chicago, the city was once a hub for furniture manufacturing, securing the nickname “Furniture City.” Today, locals and visitors alike enjoy strolling the downtown riverwalk along the Grand River, eating out at hip restaurants like Divani and Stella’s Lounge,  and shopping at the Grand Rapids Downtown Market.

The Frederik Meijer Gardens & Sculpture Park is another must-see stop, with walking trails meandering through nearly 160 acres of colorful gardens and sculptures. In the evening, sip cocktails as the sun sets at the New Hotel Marten’s hip rooftop.

Distance from Chicago: 177 miles (approx. 3 hours)

7. Madison, Wisconsin

Home to the majestic Wisconsin state capitol building, Madison is a charming city best known for its location on an isthmus surrounded by four scenic lakes. The University of Wisconsin Madison campus sprawls through the downtown area, bringing with it a vibrant artistic atmosphere as well as hip bars and restaurants. Along the pedestrian friendly State Street, boutique shops and charming cafes lead the way to the capitol building.

One of the best things to do in Madison includes visiting the Saturday farmers market, where 150 vendors line the capital square selling locally sourced produce, flowers, and sweet treats. Grabbing a pitcher of beer at the Union Terrace along Lake Mendota and visiting the admission-free Henry Vilas Zoo are also popular things to do. That said, Madison is a very outdoorsy city, so you’ll find plenty of options for everything from paddling to hiking, biking, and outdoor movies and festivals.

Distance from Chicago: 147 miles (approx. 2 hours and 20 minutes)

8. Lake Geneva, Wisconsin

Lake Geneva is a four-season resort destination in south-central Wisconsin. The city is named after the large 5400-acre Geneva Lake that attracts fishing and boating enthusiasts. The city’s Big Foot Beach State Park is one of the best places to go for swimming, sun tanning, and kayaking. If you enjoy casual walks, take a stroll along the Geneva Lake Shore Path that circles the lake for 21 miles.

While summer is an ideal time to make the most of the lake and surrounding beaches, winter also offers a unique weekend getaway. Every year, the Geneva National Resort and Club hosts the award-winning Ice Castles festival, where ice sculptures and structures amaze winter visitors. Prices and hotels cross into a variety of budget and lux options, but in general, it’s one of the cheaper towns for a summer getaway near Chicago.

Distance from Chicago: 83 miles (approx. 1 hour and 30 minutes)

Related Read:   13 Exciting Things to Do in Lake Geneva, Wisconsin

9. Saugatuck, Michigan

Saugatuck, Michigan , is an artsy beach destination best enjoyed in the summer. This small town is on Lake Michigan and Kalamazoo Lake, offering fantastic water fun like fishing, swimming, and boating. The area is also famous for its idyllic grassy dunes, Mount Baldhead Park hiking, river cruises, and the Dutch windmills and gardens in nearby Holland, MI.

The city’s center features Butler Street, where visitors can enjoy up-and-coming gourmet restaurants and boutique shops. Don’t forget to pack your swimsuit for a trip to Oval Beach. For the best experience, opt for a cozy B&B along the water or in the downtown area, but be sure to plan ahead as lodging fills fast in the summer.

Distance from Chicago: 141 miles (approx. 2 hours and 15 minutes)

10. The Wisconsin Dells

Known as the waterpark capital of the world, the Wisconsin Dells is a resort town with 20 different indoor and outdoor water parks and resorts. It’s a perfect weekend road trio from Chicago for families looking for something fun but family-friendly – and the area offers more to do than just waterparks. Take a tour along the Wisconsin River and surrounding forests on a Wisconsin Duck, an amphibious truck that dates back to WWII.

Be sure to check out other popular activities such as local winery tours, the hiking trails through nearby Devil’s Lake State Park, and the vibrant nightlife of downtown. When visiting, there are plenty of cozy Wisconsin Dells cabins to stay at if resort living isn’t for you.

Distance from Chicago: 195 miles (approx. 3 hours)

Explore More in the Midwest

10 Best Lake Camping Destinations in Wisconsin

11 Peacefully Secluded Cabin Rentals in Wisconsin

10 Awesome Glamping Getaways in Michigan

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Seen in: Illinois , Midwest , Road Trips

Posted by Brittany Varano

Brittany is a freelance travel writer and avid photographer with a love of hiking and nature. Originally from Wisconsin, she fell in love with travel blogging after living and teaching English in South Korea. She’s now location independent and enjoys slow travel to new and exciting places.

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The Best Road Trips From Chicago To Take This Fall

The best is yet to come, especially when you're going on an adventure. It's time to load up the car and head to one of these vibrant Midwest states for spectacular culture, art, and a culinary scene.

Fall is here, so it’s time to get away! While we adore our beloved Chicago, the Midwest is sprawling with beautiful and scenic cities within just a few hours of the city. Whether you want to get away to explore a stunning hiking trail or just spend the weekend roaming a charming town with cobblestone streets, there are tons of amazing things you can experience, so check out the best road trips from Chicago!

1. Madison, Wisconsin

First on our list is where Wisconsin’s capital is located, and it happens to be the second largest city in the state. Madison lies in the south-central part of the state and is centered on an isthmus between Lakes Mendota and Monona.

The proximity to the lakes makes waterside adventures a must; there are endless activities to participate in, between boating, kayaking, and swimming. After, take a stroll through the charming streets and head to one of the many breweries, or for an evening filled with serenity, head to the Olbrich Botanical Gardens , where Oblrich’s Thai Pavilion is located and is the only one in the US, and the only one outside of Thailand surrounded by a garden.

🚗 Distance from Chicago : 148 miles

🕐 Arrival Time: 2 hr and 23 mi

2. Holland, Michigan

When people think of Holland, what usually comes to mind is the Keukenhof Tulip Gardens in Amsterdam, Holland. However, you don’t need to buy an international plane ticket when another Holland is only a few hours away. This road trip from Chicago will be your new favorite getaway.

While in Holland, you’ll be able to indulge in Dutch experiences such as sprawling tulip gardens , cobblestone streets, and the picturesque Tunnel Park. With over 100 specialty shops, breweries, and restaurants, this is the perfect place to head on a road trip.

🚗 Distance from Chicago : 150.8 miles

🕐 Arrival Tim e : 2 hr 25 min

3. Traverse City, Michigan

One of our favorite Chicago trips, known as the “Cherry Capital” of the world, it’s easy to get lost in the beauty of Traverse City. Stroll along the shoreline at Grand Traverse Ba y and glance at the fluid waves as you take in a majestic sunset.

While there are many things to do in Traverse City, some of our highlights include touring the wineries, scaling a dune at the Sleeping Bear Dunes National Lakeshores, picking out some blum cherries, and immersing yourself in the beautiful lakeside town.

🚗 Distance from Chicago : 318.6 miles

🕐 Arrival Time : 4 hr 55 min

4. St. Louis, Missouri

One of the major cities in Missouri, St. Louis, lies along the Mississippi River and displays an iconic 630-foot Gateway Arch built in the 1960s. St. Louis is a quintessential city to visit, with a vibrant arts and culture scene, lively bars, and acclaimed restaurants.

This is also one of the best road trips from Chicago if you’re a fan of Chicago baseball. With Busch Stadium nearby, schedule your road trip for a game between the Cardinals and the Cubs, one of the best rivalries.

🚗 Distance from Chicago : 298.8 miles

🕐 Arrival Time: 4 hr 28 min

5. Bloomington, Indiana

Bloomington is most notably known as the home for students of Indiana University . Nestled in the rolling hills of southern Indiana, the city has spectacular foliage surrounding the town as you drive in.

Along with the visually stunning scenery , there is vibrant art, spectacular shopping, and notable restaurants—all of which support the thriving local business scene. However, it wouldn’t be right to mention Bloomington without mentioning sports. With the Big Ten, rowdy football and basketball games are an innate part of the town.

🚗 Distance from Chicago : 232.3 miles

🕐 Arrival Time : 3 hr 48 min

6. Columbus, Ohio

Along with Bloomington, Columbus is a celebrated city with a younger population due to the booming tech industry and innovative arts scene. As Ohio’s state capital , it’s one of the largest college campuses in the country.

This is one of the best road trips from Chicago if you’re looking for lively nightlife . Walking down High Street, you’ll be surrounded by reverberating music and packed patios, especially if the Buckeyes are playing.

🚗 Distance from Chicago : 356.5 miles

🕐Arrival Time: 5 hr 27 min

7. Wisconsin Dells, Wisconsin

Situated in southern Wisconsin, the Dells lies on the Wisconsin River in a region of glacier-carved sandstone formation and might be one of the most exhilarating cities on this lift. This is the best road trip near Chicago for any family planning an adventure-filled weekend .

There are numerous theme parks and entertainment centers, including Noah’s Ark Water Park and Mt. Olympus Water and Theme Park, both indoor and outdoor, spanned with waterslides, lazy rivers, rafts, and more! It’s one of the ideal road trips from Chicago for a family outing.

🚗 Distance from Chicago : 193.5 miles

🕐 Arrival Time : 2 hr 59 min

8. Saugatuck, MI

If you’re looking for award-winning beaches , scenic waterways, and verdant dunes, take a road trip to Saugatuck, Michigan. This is the ultimate escape for a quiet, luxurious weekend, with an animated art scene and renowned culinary restaurants. It’s a place that seamlessly switches from exploration to recreation for people visiting—making it one of the best road trips from Chicago.

🚗 Distance from Chicago : 145.8 miles

🕐 Arrival Time : 2 hr 19 min

9. Ann Arbor, MI

While many of the Michigan cities listed here are located along Lake Michigan, Ann Arbor is one the few recognized as an urban oasis in the middle of the state. The downtown scene is from a storybook with a red-brick main street filled with independent bookstores, locally-made candle shops, home goods, and more.

While there’s a lot to do downtown, head outside the city to explore the nature parks surrounding the town, which have some of the most scenic hiking trails.

🚗 Distance from Chicago : 241.3 miles

🕐 Arrival Time : 3 hr 45 min

10. Sheboygan, Wisconsin

Deemed the “Malibu of the Midwest, ” Sheboygan, Michigan, might not have five-foot waves like the West Coast. Still, it’s a freshwater haven for anyone who loves fishing, sailing, and surfing, from outdoor recreational activities like golfing and biking to events and festivals that highlight the art scene, cultural heritage, and vibrant music, it’s no wonder it’s one of the best road trips from Chicago.

🚗 Distance from Chicago : 147.6 miles

🕐 Arrival Tim e: 2 hr 24 min

11. Cincinnati, Ohio

Cincinnati is a beloved Midwestern city—right on the border of Northern Kentucky—some say it’s where metropolitan vibrancy meets Kentucky’s southern flair . From a wild sports fandom, you can catch Joe Burrow throwing a football or Joey Votto singing his bat, all less than a 1/2 mile from each other. However, besides athletics, there are splendid places to explore within Cincinnati, and it’s one of the ideal road trips from Chicago.

🚗 Distance from Chicago : 295.4 mi

🕐 Arrival Tim e: 4 hr 32 min

12. Petosoky, Michigan

Petoskey, Michigan, is one of the road trips from Chicago that will offer beautiful fall foliage . The autumn days are filled with bleeding sunset colors. Whether you’re looking for a Fall Festival , a cider mill, or a cozy brewery, you can find it here.

🚗 Distance from Chicago : 361.3 mile

🕐 Arrival Tim e: 5 hr 44 min

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Where to Road Trip from Chicago: 12 Interesting Destinations

• Date: July 18, 2022
• Time to read: 6 min.

There are a lot of great destinations from Chicago! If you have a day or a week, these interesting cities and attractions are great places to visit  on a road trip this summer. 

When you are planning a vacation on a budget there there three factors to consider:

You have control over all these costs, but gas will cost what gas will cost. You have find something closer to home. 

I have a list of destinations that can be exciting no matter how close or far from home your budget can carry you. 

Day Trips from Chicago

These trips will take about an hour from the city and include some really cool sites to see. 

The Vine Martini and Wine Bar

In Greyslake Illinois The Vine is a very popular bar. The relaxed atmosphere of The Vine makes it a great place to visit from Chicago. 

Right down the street there is a great burger place, Twisted Burger and Emil’s Tavern. A great place to spend the evening with friends. 

Cedar Lake (Indiana) 

Cedar Lake is a great trip for hunting for antiques. The Old Goat’s market is a good first stop and you can enjoy learning about the area at the Cedar Lake Historic Museum. 

There are a number of other antique and resale shops for a day of deal hunting. 

Michigan City

Michigan City is just a short drive from Chicago and you can find Casinos, restaurants, outlet shopping and you will cross state lines! 

If you are not into gambling, the lighthouse museum is a high quality educational trip and the outlet shopping is a great girls trip idea. Michigan city is an exciting day trip from Chicago. 

2-3 Hour Trips from Chicago

A two hour trip is a really good distance for traveling with kids or young babies. Experienced travelers often travel for 2-3 hours max between stops. 

Take a page from their book and stop before you get too tired of driving. 

Menomonee Falls

Menomonee Falls is a beautiful destination. The falls are man made waterfall located in Mill Pond Park. The city was once home to a large sugar mill. 

There are a lot of beautiful walking trails, ponds and river walks to enjoy in Menomonee Falls. There are also sunset beer garden events in warm weather. 

Crane Orchards U-Pick and Corn Maze, Fennville, Michigan 

A great fall destination , the Crane Orchards and Corn Maze in Fennville Michigan is a destination worth the drive. 

Be sure to pack your walking shoes and enjoy picking cherries, peaches, apples and pumpkins in season. You can find their seasonal fruit page to let you know what is available to pick. 

I love marking apple picking on my family’s calendar each fall. It is a beautiful memory and such a fun day. 

Davenport Iowa

Right on the banks of the Mississippi Davenport is a great small city. Davenport is considered one of the Quad Cities. 

This area offers riverfront dining, walking trails, shopping, theater and museums. 

The Adler Theater offers comedian tours, live music and Broadway shows. Follow up your show with a river cruise and dinner. 

This vacation is really shaping up and you drove less than 150 miles! 

Indianapolis, Indiana 

There is a large museum in Indianapolis that contains the best preserved T-rex in existence, your dino lover will never forget this three hour drive out of Chicago. 

The museum associate with the Indianapolis Speedway is engaging even if you have never seen a race. When the track is not in use you can take the bus tour of this iconic track. 

Monument circle in the heart of town hosts a farmer’s market, food trucks, coffee and restaurants. This busy area of town has plenty to see and do. 

3-5 Hour Trips from Chicago

Three to five hours is the longest drive I would recommend that you drive without stopping, but you will feel like you really got away. 

If you are traveling with kids I recommend that you read this post about how to plan stops with kids . 

Bowling Green, OH

Bowling Green is a great place to attend really great events and festivals. The National Tractor Pulling competition is hosted here and the Great Black Swamp Art Festival.

They have a wonderful summer activity calendar that is sure to offer something worth seeing.   

Bloomington, IN

If you would like a slower paced trip, head to Bloominton. The small town feel offers plenty to see and do. 

Art museums, sculpture gardens and science museums offer plenty of things to do for the whole family. 

The Wonder Lab Science Museum is a hands-on science museum for the whole family and it would make a great family event. 

St. Louis, MO

Our family has taken several trips to St. Louis and you can read about our favorite STL destinations in the linked post. There is no limit to what you can do in St. Louis. 

When you visit St. Louis you will want to see the Arch, the gateway to the West. The improved grounds are a lovely place to walk and read more about American history. 

There are also a few foods you will want to try while visiting the city:

Frozen Custard

Toasted Ravioli 

St. Louis Style Pizza

The first time I tried pizza from Imo’s Pizza I was surprised. It is a memorable experience, give it a try. 

6-8 Hour Trips from Chicago

Chicago is a great starting point when you want to explore America. If you can budget to drive six to eight hours you will be able to visit some iconic American cities and attractions. 

Erie has the best city website I have seen. There is so much to do in Erie, water parks, historic tours of Lake Erie and AA baseball. 

Request a guide to Erie on their city website. It will give you the most information about how to spend your time in this vibrant diverse city. 

Nashville, TN

Nashville is an unforgettable trip. There is so much to see and hear in Music City. 

The Nashville Zoo is great day or night. Their night light display is a stunning event and a low stress evening event. 

You may also choose to schedule your trip around their incredible Food and Wine Festival. The city has the best hotels and restaurants for any budget. 

You will want to hear some music and venues abound. Check out the calendars for: 

Storytellers Hideaway

Grand Ole Opry 

Ryman Auditorium 

RCA Studio A 

Mammoth Cave National Park

Mammoth Cave National Park is a beautiful destination for camping, hiking, exploring and soaking in nature. 

National Parks can book up quickly so check out my handy guide to when to book your road trip lodging. 

Large families or large groups will enjoy the flexible lodging options in National Parks. I highly recommend this for a family vacation. 

Niagara Falls

Niagara Falls is a bucket list item for many people and it is just a few hours from Chicago!

This popular international tourist destination should be planned well in advance. Check lodging prices frequently and plan accordingly. 

One tip for creating a low stress vacation plan is to hire a local guide. I highly recommend that you consider planning this trip with a travel agent or local guide company so that you can avoid getting stuck in a crowd and missing the experience you dreamed about. 

Memphis, TN

Memphis is the home of bluegrass, soul music and rock and roll. This is an incredible destination for music lovers. 

This is about as far south as you can drive from Chicago in 8 hours , so if you are looking to warm up Memphis is a great destination. 

Festivals, concert cities and museums are all waiting in memphis. 

They have several immersive art experiences as well as a trolly tour that is sure to delight. 

Planning a Road Trip From Chicago

When you are planning a road trip from Chicago I recommend that you start at WithinHours.com this site will allow you to explore different travel radius options from your city.

This can help you uncover hidden gems that you may never have thought of in your area. 

Follow up with this Road Trip Planning guide with a few printable worksheets that can help you stay organized and on budget.

• What Is a Good Budget For A Family Road Trip?
• Can you Drive Over Hoover Dam? Cost, times and details

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Best Road Trips from Chicago: Exploring the Great Lakes Region

I f you’re looking for an adventure that’s not too far from Chicago, a road trip might be just what you need. The Midwest is full of hidden gems waiting to be discovered, and there are plenty of road trips from Chicago that will take you to some of the best spots. Whether you’re looking for a quick weekend getaway or a longer trip, there’s something for everyone.

One of the best road trips from Chicago is the Great River Road in Illinois. This scenic drive takes you along the Mississippi River and through charming towns like Galena and East Dubuque. You’ll see historic sites, beautiful scenery, and plenty of opportunities for outdoor activities like hiking and fishing. The drive takes about 3.5 hours, making it a great option for a weekend trip.

Another great road trip is to Harbor Country, Michigan. This idyllic shoreline in Michigan’s southwestern corner stretches from the Indiana border to the town of Sawyer and is only 1 hour and 20 minutes from Chicago. Harbor Country is one of the most popular getaway destinations for Chicagoans.

You’ll find picturesque beaches, quaint towns, and plenty of opportunities for outdoor activities like hiking and biking. Whether you’re looking for a relaxing beach vacation or an active adventure, Harbor Country has something for everyone.

Understanding Road Trips

Going on a road trip can be an exciting and memorable adventure, but it requires some planning to ensure a successful trip. In this section, we’ll discuss the importance of planning and choosing the right vehicle for your road trip.

Importance of Planning

Planning is crucial for a successful road trip. By planning ahead, you can ensure that you have everything you need for the trip and avoid any unexpected surprises. Here are some things to consider when planning your road trip.

• Route: Decide on your route and plan your stops and attractions along the way. Use online maps or road trip planning websites to help you plan your route.
• Accommodations: Book your accommodations in advance to ensure you have a place to stay each night. Consider staying in hotels, motels, or even camping if you prefer.
• Budget: Plan your budget for the trip, including food, gas, and any activities or attractions you plan to visit.
• Packing: Pack everything you need for the trip, including clothes, toiletries, snacks, and any necessary equipment or supplies.

By planning ahead, you can ensure that your road trip is enjoyable and stress-free.

Choosing the Right Vehicle

Choosing the right vehicle for your road trip is also important. You want a vehicle that is comfortable, reliable, and can handle the terrain and weather conditions of your route. Here are some things to consider when choosing a vehicle.

• Size: Consider the size of your group and the amount of luggage or equipment you’ll be bringing. Make sure the vehicle has enough space to accommodate everything comfortably.
• Fuel Efficiency: Choose a vehicle that is fuel-efficient to save money on gas during your trip.
• Comfort: Look for a vehicle that is comfortable to ride in for long periods of time. Consider features like air conditioning, comfortable seats, and plenty of legroom.
• Reliability: Choose a vehicle that is reliable and has a good track record for safety and performance.

By choosing the right vehicle, you can ensure that your road trip is comfortable, safe, and enjoyable.

Remember, planning ahead and choosing the right vehicle are key to a successful road trip. With a little preparation, you can have a memorable adventure on the open road.

Chicago: The Starting Point

If you’re looking for a great starting point for a road trip, look no further than Chicago. This bustling city is located in the heart of the Midwest , making it the perfect jumping-off point for exploring the region. Whether you’re looking for natural beauty, historic sites, or big-city excitement, there’s something for everyone within a few hours’ drive of Chicago.

One of the best things about starting your road trip in Chicago is the sheer number of options available to you. From the city itself to the surrounding suburbs and countryside, there’s no shortage of things to see and do. Plus, with major highways like I-90 and I-94 passing through the city, it’s easy to hit the road and start your adventure.

If you’re interested in exploring the city before you hit the open road, there’s plenty to keep you busy. Take a stroll through Millennium Park and snap a selfie in front of the famous Bean sculpture. Visit the Art Institute of Chicago to see some of the world’s greatest works of art. Or take a stroll down the Magnificent Mile for some world-class shopping.

Once you’re ready to hit the road, you’ll find plenty of options for road trips from Chicago. Head north to explore the shores of Lake Michigan, or head south to experience the rolling hills of southern Illinois. Or, if you’re feeling ambitious, head west to explore the Great Plains and the Rocky Mountains.

No matter which direction you choose, you’re sure to find plenty of adventure and excitement on your road trip from Chicago. So pack your bags, hit the road, and get ready for an unforgettable journey through the heart of America.

Midwest Gems: Stops to Make

If you’re planning a road trip from Chicago, the Midwest offers plenty of hidden gems to explore. Here are a few must-see stops to add to your itinerary.

Milwaukee, Wisconsin

Just a two-hour drive north of Chicago, Milwaukee has something for everyone. Known for its breweries and cheese curds, the city also boasts beautiful lakefront views, historic architecture, and a thriving arts scene. Be sure to check out the Milwaukee Art Museum, the Harley-Davidson Museum, and the Pabst Mansion.

Minneapolis, Minnesota

A six-hour drive northwest of Chicago, Minneapolis is worth the trip. The city is home to numerous parks and lakes, including the famous Chain of Lakes. Minneapolis is also known for its food scene, with plenty of trendy restaurants and food halls to check out. Don’t miss the iconic sculpture garden at the Walker Art Center.

Fargo, North Dakota

If you’re up for a longer drive, Fargo is a unique destination to consider. The city is known for its friendly locals, quirky attractions, and rich history. Check out the Fargo Air Museum, the Plains Art Museum, and the iconic woodchipper from the movie Fargo. And of course, don’t forget to take a photo with the famous “largest buffalo statue” in nearby Jamestown.

No matter which Midwest gems you choose to visit, you’re sure to find plenty of charm, culture, and adventure along the way.

Scenic Routes to Consider

If you’re looking for a scenic road trip from Chicago, you have plenty of options to choose from.

Great River Road

The Great River Road is a scenic byway that follows the Mississippi River from its headwaters in Minnesota to the Gulf of Mexico. The Illinois portion of the Great River Road runs for 550 miles along the western border of the state. The road takes you through charming river towns, past historic sites, and offers stunning views of the Mississippi River.

Some highlights of the Great River Road in Illinois include:

• Galena : This charming town is known for its historic architecture, quaint shops, and scenic views of the river.
• Mississippi Palisades State Park : This park offers hiking trails, camping, and stunning views of the river from its bluffs.
• Nauvoo : This historic town was once the headquarters of the Church of Jesus Christ of Latter-day Saints. Today, it’s a popular tourist destination with historic sites and beautiful views of the river.

Lake Michigan Circle Tour

The Lake Michigan Circle Tour is a 1,100-mile scenic route that takes you around Lake Michigan. The route passes through four states: Illinois, Indiana, Michigan, and Wisconsin. The Illinois portion of the tour takes you along the eastern shore of Lake Michigan, from Chicago to the Wisconsin border.

• Chicago : The tour starts and ends in Chicago, a world-class city with plenty of attractions to explore.
• Indiana Dunes National Park : This park offers 15 miles of sandy beaches, dunes, and hiking trails along the southern shore of Lake Michigan.
• Illinois Beach State Park : This park offers swimming, hiking, and camping along the shores of Lake Michigan.
• North Point Lighthouse : This historic lighthouse in the town of Lake Bluff offers stunning views of the lake and surrounding area.

No matter which route you choose, you’re sure to find plenty of scenic views and interesting attractions along the way.

Preparing for the Journey

Before embarking on your road trip from Chicago, it’s important to prepare for the journey ahead. This includes packing essential items and ensuring that your vehicle is in good condition.

Packing Essentials

Packing for a road trip requires some planning to ensure that you have everything you need without overpacking. Here are some essential items to consider bringing with you:

• Maps or a GPS device : Even if you have a GPS device, it’s always a good idea to bring a physical map as a backup.
• Snacks and drinks : Pack non-perishable snacks and drinks to keep you fueled up during your journey.
• First Aid Kit : It’s always better to be safe than sorry. A basic first aid kit can come in handy in case of minor injuries.
• Comfortable clothing and shoes : Pack comfortable clothing and shoes that are appropriate for the weather and any activities you plan to do.
• Entertainment : Bring books, music, or games to keep you entertained during long stretches of driving.

Vehicle Maintenance

Before hitting the road, it’s important to ensure that your vehicle is in good condition.

• Oil change : Get an oil change if it’s due or overdue.
• Tire pressure : Check your tire pressure and inflate them to the recommended level.
• Fluid levels : Check your vehicle’s fluid levels, including brake fluid, coolant, and transmission fluid.
• Brakes : Have your brakes checked to ensure that they are in good condition.
• Battery : Check your battery to ensure that it’s in good condition and fully charged.

By packing essential items and ensuring that your vehicle is in good condition, you can have a safe and enjoyable road trip from Chicago.

Adventures Beyond the Midwest

If you’re looking for a longer road trip adventure, there are plenty of options beyond the Midwest. Here are two popular road trip destinations that are worth the extra mileage.

Rocky Mountain Road Trip

Head west for a Rocky Mountain road trip that will take you through some of the most stunning natural landscapes in the country. Start in Denver, Colorado, and drive through the Rocky Mountains to see towering peaks, crystal-clear lakes, and picturesque valleys. Stop in Boulder for a hike up to the Flatirons or a stroll down Pearl Street, a pedestrian mall with plenty of shops and restaurants.

From there, drive through the Rocky Mountain National Park to see elk, bighorn sheep, and other wildlife in their natural habitats. You can also take a scenic drive along the Trail Ridge Road, which offers breathtaking views of the mountains and valleys below.

Pacific Coast Highway

For a road trip with a coastal view, head west to California and drive along the Pacific Coast Highway. Start in San Francisco and drive down the coast to Los Angeles, stopping at scenic beaches, charming towns, and iconic landmarks along the way.

In San Francisco , take a walk across the Golden Gate Bridge or visit Alcatraz Island. In Big Sur, stop at Pfeiffer Beach to see the famous Keyhole Arch or take a hike through the redwood forests at Julia Pfeiffer Burns State Park. In Los Angeles, visit the Hollywood Walk of Fame or take a stroll down Venice Beach.

No matter which road trip you choose, be sure to pack plenty of snacks, water, and supplies for the journey. And don’t forget to take breaks and enjoy the scenery along the way!

Final Thoughts on the Best Road Trips from Chicago

There are many road trip options to explore from Chicago. Whether you’re looking for a quick weekend getaway or a longer adventure, there is something for everyone.

Some of the most popular road trips from Chicago include heading to St. Louis, Indianapolis, or Milwaukee. These cities offer a mix of urban and outdoor attractions, making them great destinations for families, couples, or solo travelers.

If you’re looking to get out into nature, consider visiting the Indiana Dunes National Park or the Upper Peninsula of Michigan. Both offer stunning natural beauty and a range of outdoor activities, including hiking, biking, and kayaking.

For those interested in history, the Route 66 road trip is a must-do. This iconic highway stretches from Chicago to Santa Monica, California, and offers a glimpse into America’s past.

No matter which road trip you choose, be sure to plan ahead and pack accordingly. Consider renting a car or RV to make the journey more comfortable, and don’t forget to bring snacks, water, and a camera to capture all the memories. Happy travels!

Frequently Asked Questions about Best Road Trips from Chicago

What are some of the best midwest road trips to take from chicago.

Chicago is the perfect starting point for a Midwest road trip.

• St. Louis, MO : This city is known for its beer, blues, and BBQ. It’s only a 4.5-hour drive from Chicago and definitely worth the trip.
• Indiana Dunes, IN : Only an hour away from downtown Chicago, Indiana Dunes became the newest National Park in the United States in 2019.
• Mississippi River Drive to East Dubuque, IL : This drive along the Mississippi River is filled with historical sites and activities. Moline and Rock Island are two cool detours, but East Dubuque is a must-visit for its Chicago Great Western Railway Depot Museum.

What are some day trip options in Southern Illinois from Chicago?

• Starved Rock State Park : This state park is only a 2-hour drive from Chicago and offers beautiful hiking trails and waterfalls.
• Shawnee National Forest : This national forest is known for its beautiful scenery and hiking trails. It’s only a 5-hour drive from Chicago.
• Galena, IL : This charming town is known for its historic architecture and quaint shops. It’s only a 3-hour drive from Chicago.

What are some warm destinations to drive to from Chicago?

• Nashville, TN : This city is known for its live music and southern charm. It’s only an 8-hour drive from Chicago.
• New Orleans, LA : This city is known for its delicious food and lively atmosphere. It’s a 13-hour drive from Chicago, but definitely worth the trip.
• Gulf Shores, AL : This beach town is perfect for a relaxing getaway. It’s a 12-hour drive from Chicago.

What are some great road trips from Chicago for couples?

• Door County, WI : This charming town is known for its beautiful scenery and quaint bed and breakfasts. It’s only a 4-hour drive from Chicago.
• Traverse City, MI : This city is known for its wineries and beaches. It’s a 6-hour drive from Chicago.
• Lake Geneva , WI : This town is known for its beautiful lake and charming downtown area. It’s only a 2-hour drive from Chicago.

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What are some family-friendly road trip options from Chicago?

• Wisconsin Dells, WI : This city is known for its water parks and family-friendly activities. It’s only a 3-hour drive from Chicago.
• Mackinac Island, MI : This island is known for its beautiful scenery and family-friendly activities. It’s a 7-hour drive from Chicago.
• Springfield, IL : This city is known for its history and family-friendly attractions, such as the Abraham Lincoln Presidential Library and Museum. It’s only a 3-hour drive from Chicago.

What are some short road trips that can be taken from Chicago?

• Milwaukee, WI : This city is known for its breweries and museums. It’s only a 1.5-hour drive from Chicago.

The post Best Road Trips from Chicago: Exploring the Great Lakes Region appeared first on Traveling Cheesehead .

10 Road Trips From Chicago That Make Leaving The City Worth It

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Skip Seattle: Visit Its Underrated, Upscale Alternative

Get paid up to $32,000 to move to tuscany, 7 mountain towns in north carolina that have asheville vibes, but better.

Chicago is undeniably one of the best cities to live in America. Even with the city’s convenience, sometimes Chicago feels like a bunch of blocks with no thrill. Summer is the best time to explore the thrill, and moving out of Chicago seems to be the real deal.

Driving away from the chaotic and normal life of the city is an underrated experience that vacationers need to explore more often.

Here are 10 road trips from Chicago worth the effort.

10 Cincinnati, Ohio

In the recent past, the state of Ohio continues to tick all the right boxes in tourism matters. This time around, it is the city of Cincinnati serving some deserved justice to the state. From its natural resources to the beautiful skyline, the thrill in this city is virtually endless. The Ohio River is a tantalizing beauty that vacationers will truly love.

• Driving Time: Five hours

Related: This Is The Best Month To Visit Chicago & Why You’ll Want To Go

9 Galena, Illinois

The beauty of a road trip doesn't solely depend on the distance traveled. The experience matters too. With Galena, it is more about the experience than the traveling time. It is among the most historical cities in modern-day America. The city has stuck with architectural designs from the early 19th century. The city has lived to the billing of one of America’s most conservative regions. Also, the delicacies served in this part of Illinois are worth the drive.

• Drive Time: Five hours

Related: Chicago, Illinois: Planning The Perfect Weekend

8 Starved Rock State Park, Illinois

The Starved Rock State Park is the best way to experience Illinois' wild side. In fact, this park is worlds apart from anything else in Illinois. From the beautiful vegetation covering the area to the free-flowing waterfalls in the park, vacationers are rewarded greatly for their courage to drive out of Chicago. While at the park, vacationers have multiple activities to explore including hiking and biking. During the warmers months, adventures will have a good time soaking in the waterfall before they dry up.

• Drive Time: One hour 30 minutes

7 Bloomington, Illinois

What is it about college towns that vacationers want to spend more time in those areas yet the population is so high? Well, college towns have a special kind of vibe since they are dominated by youthful individuals. With Bloomington, vacationers have more than just the young people vibe. It is also a great interaction with nature. Surrounded by thick forests and lakes, this neighborhood gifts tourists a lot to explore. Going out fishing in any of the reservoir lakes in the region and bringing the catch back to Chicago is part of the experience that creates a lasting memory.

• Drive Time: Four hours

6 McHenry County, Illinois

McHenry is another perfect escape route from Chicago. It is the place to be for individuals who like visiting parks. But who doesn’t anyway? These parks provide the perfect places for vacationers to interact with nature. Apart from the park, it is the best place to understand what buying local build local means. To them, it is local products first and the rest come second. Enjoy some of the most authentic frozen custard in any of the county's dairy farms.

• Driving Time: One hour 30 minutes

5 Lake Geneva, Wisconsin

What is the best description of the ultimate Chicago road trip? Whether long or short, the quality of a specific road trip boils down to the activities available for the vacationers to explore. The Legendary Lake Geneva needs no introduction as its general appeal speaks volumes. This lake forms a reasonable escape route with multiple activities for vacationers to explore.

4 Springfield, Illinois

Road trips are not a preserve for nature enthusiasts alone. Historians as well have an equal opportunity and that’s what Springfield is all about. One of America’s liberators in President Abraham Lincoln has its roots in this town. One of the must-do activities for vacationers in Chicago is visiting his tomb at the Oak Ridge Cemetery is a great way to connect with American history.

• Drive Time: Three hours

3 Louisville, Kentucky

Louisville is by far the largest city in Kentucky and a great place to visit. Vacationers seeking an escape route away from Chicago find this city to be a great choice. From its incredible shoreline to the multiple distilleries to be explored, this city is indeed a must-visit for road trip enthusiasts.

2 Mammoth Cave National Park, Kentucky

Once again, it is mighty Kentucky doing the magic for Chicago vacationers. It is the world’s largest cave system with more than 400 miles of underground pathways. Also, it is one of the longest road trips away from Chicago. With six hours of driving, this trip would be best pursued for a weekend.

• Drive Time: Six hours

1 South Haven, Michigan

Vacationers driving out of Chicago in search of a better thrill find a good one in South Haven. It is a small port city in Michigan barely two hours away. This city is a bit laid back compared to Chicago’s chaotic nature. From exotic restaurants to relaxed beaches, South Haven automatically becomes the perfect escape route away from Chicago.

• Driving Time: Two hours
• Springfield

Windings to Unwind

Chicagoland’s Best Road Trips and Outdoors Guide since 2020 .

14 Summer Road Trip Ideas from Chicago (Updated For 2024)

From a quick 3-hour Chicago weekend getaway to 16 hours jaunt to the Rockies for seasoned road trip connoisseurs – use this Mega Chicago Road Trip thread to know more about 14 curated, off-beat Summer Road Trip ideas from Chicago – including nearest oceanfront beach from Chicago, dreamy Michigan coast towns, bridge walk under the…

“ We travel not to escape life, but for life not to escape us.” – this anonymous quote succinctly captures the spirit of every family planning their next road trip adventure.

Whether you just want a quick 3-hour Weekend Chicago Getaway or have the tenacity for an epic 16-hour road trip to the Rockies as a seasoned road tripper – this mega road trip blog details 14 Road Trips from Chicago with itineraries, pictures and thoroughly researched Things-To-Do.

The ancient ‘New River’ – as seen from the Endless Wall Trail during Chicago to West Virginia road trip

Criteria for these road trips? Every one of these road trips: – has plenty of activities for both family and friends, whether it is family-friendly touristy spots, nature outings or adrenaline-pumping activities for thrill seekers. – has mine (and many other fellow travelers’) first-hand feedback . This is not one of those posts which is *aggregating* stuff already available from Google or your favorite AI search engine.

Without further ado, in order of the *least* travel time from Chicago –

1. Saugatuck and Douglas (Michigan)

Min Days Required: 2 days. Distance: 200 miles . ETA: 3 hours . Why visit? Saugatuck &Douglas are highly renowned Michigan coastal towns and a great destination for beachgoers, nature lovers and artists .

Find more details here at the official Saugatuck portal. PHOTOLOG

Root Beer Barrel Stand at Douglas

2. Door County (Wisconsin)

Min Days Required: 2 days. Distance: 280 miles . ETA: 4 hours . Why visit? Door County is not just a Fall Colors novelty, it is truly one of the best weekend getaways for Chicago residents – few hours of drive gets you to a series of tourist-friendly, charming coastal Wisconsin towns bordering Lake Michigan. Door Peninsula is juxtaposed with waters of Green Bay on one side and Lake Michigan on the other, leading to smashing waterfront views.

Touristy activities – Cherry and/or berry picking, golfing, local wineries and summer festivals. For Nature Lovers – Biking and hiking at Peninsula State Park (rentals available as well), many other picturesque hiking trails . Tip: Take a ferry to Washington Island and enjoy almost a day of touristy activities – Cherry Train Tour , Hiking around the island, Lavender farm .

Here is the great official website for list of all Door County activities on offer during summer.

3. St Louis (Missouri) and Springfield (Illinois)

Min Days Required: 3 days. Distance: 300 miles . ETA: 5 hours . Why visit?

Touristy spots – The iconic Gateway Arch (don’t miss the ride which takes you all the way to the top of the arch), Monstrocity play area with giant slinky tunnels (thrilling for kids and adults alike), Grant’s Farm. For Nature Lovers – Meramec Caverns, Lone Elk Park (famous for elk, bison and a lot of other wildlife). For Adventurists – Ziplines at Meramec caverns.

The Stalactite formations at Meramec Caverns

The Meramec Caverns have rich human history as well

Monstrocity , photo by Laurie Skriva, [email protected]

The center dome at the Capitol of Illinois

4. Adventure Road Trip to Niagara, WI.

Minimum Days Required: 3 days . Distance: 300 miles . ETA: 5 hours with many breaks along the way. Why visit? Wide assortment of adventure activities for kids and adults, just 5 hours away. Best part is the simplified logistics since lodging, activities and even food is managed by Wildman itself. White-water Rafting – Wildman Resort is one of the nearest and well-managed white-water rafting spots from Chicago. Other adventure activities – zip-lining , paintball, kayaking, climbing. Camping by the Peshtigo River.

Check out the full blog with pictures and itinerary here .

5. Put-in Bay (Ohio)

Minimum Days Required: 3 Distance: 320 miles . ETA: 6 hours with couple of breaks. Why visit? Quaint Ohio island village on Lake Erie with a ton of family fun/adventure activities. You can also combine it with Cedar Point Amusement Park at Sandusky. Touristy spots – Benson Ford Ship House , Underground Perry Cave adventure , local wineries, tour train, butterfly house.

Tip: Also check out the official portal here with infodump on tons of activities.

6. Traverse City, Sleeping Bear Dunes, River Tubing (Michigan)

Minimum Days Required: 3 Distance: 360 miles . ETA: 7 hours with couple of leisurely breaks. Why visit? A perfect intermix of water, sand and urban activities. Touristy spots – Traverse City has something for everyone – vineyards and wineries, dozens of beaches, food and entertainment. For Nature Lovers – Sleeping Bear Dunes with its emblematic bluffs, dunes and the eponymous Dune Trail to Lake Michigan; canoeing, kayaking and floating at the natural lazy river – Platte River ; Biking, paddle-boarding, kayaking, sunset-sails as organized by The River Outfitters and finally, all the camping options. Tip: Try to merge your road trip with one of the many scenic drives MI has to offer.

7. Cuyahoga National Park (Ohio)

Minimum Days Required: 3 Distance: 380 miles . ETA: 7 hours with couple of leisurely breaks. Why visit? A lesser known national park but with all the perks. Touristy spots – Cuyahoga Valley Scenic Railroad. For Nature Lovers – Brandywine falls, Biking across the historical Ohio/Erie canal Towpath trail and finally, The Ledges Trail , a moderate 1.8 mile hike abundant of vivid rock formations and cliffs, making it truly one of a kind.

Check out the detailed blog with itinerary and pictures here .

8. Red River Gorge (Kentucky)

Minimum Days Required: 4 Distance: 440 miles . ETA: 8 hours with couple of leisurely breaks. Why visit?

Rock Climbing /rappelling – Red River Gorge or The Red as it is called, is known for the best climbing crags in the nation, perfect for rock climbing/rappelling. Underground Kayaking – an exhilarating experience of Kayaking in almost pitch dark in a forgotten underground mine, accompanied by chilling temperatures even when its 90 degrees outside the cave.

Red River – A water fest for the kids: boasting of activities like Cliff jumping, Kayaking, River Tubing. Scenic Overlooks, trails, scenic drives, streams. Bonus: Cumberland falls (also known as Niagara of the South ) is couple of hours away from Red River Gorge area and the only place in the Western Hemisphere where you can see a moonbow in action.

Check out the full blog with detailed itinerary and pictures here .

9. Mackinac Island

Minimum Days Required: 3 Distance: 440 miles . ETA: 8 hours with couple of leisurely breaks. Why visit? Touristy spots – Mackinac Island is truly one of a kind – with no cars allowed inside, most of the island is preserved as the state park and offers a ton of historical, touristy and nature-friendly activities. No wonder it attracts a bazillion tourists each year. For Nature Lovers – The 8.2 mile bike trek around the island with serene Lake Michigan views, is as good as it gets . You can also visit Tahquamenon Falls State Park , known for hosting a series of waterfalls plunging into Lake Superior. For those looking a natural swimming holes, you can also take a dip in the Lower Falls at Tahquamenon, a family-friendly swimming site. Tip: Mackinac Island bifurcates Upper and Lower Peninsula, which gives you a unique opportunity to travel up north to places like Pictured Rock and Soo Locks. . If you want to savor Lower peninsula, you can visit Traverse City and some of other favorites – river tubing at the Platte River and the scenic M31 highway tracing through Elk Rapids, Charlevoix and Petoskey.

A monarch taking its flight, at Wings of Mackinac Butterfly Conservatory

10. New River Gorge at Fayetteville (West Virginia)

Min Days Required: 4 Distance: 570 miles . ETA: 9 hours . Why visit? Adventure activities – white-water rafting, bridge walking, ATV rides, rock climbing, rappelling and a lot more. A Nature Lover’s paradise – Trails, scenic drives, panoramic vistas, ancient forests, rivers. Endless Wall Trail is voted #1 trail in the nation in many polls – I have never seen such stunning views accessible via a gentle 2.3 mile out-and-back hike. And all this while, you would hike through the ancient Hemlock forest rich in local flora. Long Point trail comes a close second, another gentle hike with dazzling views of the symbolic New River Gorge bridge.

Check out the full blog detailing our road trip here .

Tip: The key to visit so many places in a short trip (3-4 days) and not rush through the things, is to simplify the logistics. I stayed and booked most of these adventure activities directly from Ace Adventure Resort whom I found very reliable and resourceful. Would highly recommend Ace Adventure for any of your visits near the area – their Wipeout style water park over an *actual* lake is a kids paradise.

11. Smokey Mountains National Park

Minimum Days Required: 4 Distance: 600 miles ETA: 11 hours with multiple breaks Why visit? Plenty of Touristy spots for family – Gatlinburg downtown including Skylift, the Little River Scenic Drive , Pigeon Forge’s amusement parks – huge hit with kids. For Nature Lovers – Plenty of hiking options, notably – Laurel Falls, Gretto Falls, Clingmans Dom – highest point at Smoky with stunning views, Cades Cove – your best chance at live bear sighting. For Adventurists – Rafting (we did it with kids as young as 8 at the Lower Pigeon River), Zip-Lining, River Tubing at The River Rat Main Outpost.

Check out the full blog with itinerary and pictures here .

Smokey 101 – The SkyLift Bridge (Don’t miss the night view)

12. Chattanooga and Nashville (Tennessee)

Distance: 630 miles . ETA: 11 hours with couple of leisurely breaks. Why visit?

Touristy spots – The Rock City which boasts a vantage point where you could see 7 states, Ruby Falls (underground waterfall), Lookout Mountain (known for the epic Civil War battle), Incline Railway (one of the steepest funicular railway incline in the world), Point Park . You can also visit Parthenon in Nashville on the way to Chattanooga. For Nature Lovers – We did the Cherokee Falls trail in Cloudland Canyon State Park. Detailed list of all trails is here. For Adventurists – Ziplines at Ruby Falls.

13. Pensacola (Florida) and Gulf Shores (Alabama)

Distance: 900 miles . ETA: 14 hours with a few short breaks. Why visit? One of the closest ocean fronts from Chicago, Pensacola/Gulf Shores area is renowned for its pristine white sand beaches rich in quartz.

Touristy spots – Fort Pickens , Scenic Highway 30A , Okaloosa Island Fishing Pier , Pensacola Naval Air Station – home of the Blue Angels , Crabs , Fort Morgan .

For Nature Lovers – Bayou Marcus Birding Trail , Northern Terminus of Florida National Scenic Trail , Tarkiln Bayou Trail (known for Pitcher plants ).

Water sports should definitely be on the menu as well. Tip: Nashville area would be a perfect pit stop for this road trip. You can also visit Parthenon on the way.

14. Rocky Mountains National Park

Distance: 1000 miles . ETA: 16 hours, best to span it across 2 days. Why visit? With 400+ miles of mountain environments, 300 miles of pristine hiking trails, sparkling alpine lakes, waterfalls, gushing rivers, meadows and towering mountain peaks, the Rockies tick all the boxes for an epic road trip!

Other Touristy activities – Camping, ATV rides, White-water rafting , driving up or taking a train to Pikes Peak (one of the highest motor-able roads in America), drive to Trail Ridge Road, Bear Lake, Lilly Lake and finally, Garden of the Gods.

Here is the super helpful NPS portal for list of all activities on offer.

Here is the full blog detailing our road trip. Tip: The weather at the Rockies could be quite shifty, it snowed heavily right before our Memorial Day trip. Please check the official weather updates here.

Vistas like above is a routine sight at the Rockies!

That’s all there is!

If you made it this far, hopefully you found your next road trip adventure from Chicago.

Like what you see? View our X or Reddit exploits.

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3 responses to “14 summer road trip ideas from chicago (updated for 2024)”.

Awesome post — I’ve been over that bridge and it is wild! If you go that way again, check out Middleboro, Ky— it’s just a mountain town, but it was build in an asteroid crater about ten miles wide.

Thanks for the suggestion for Middleboro, KY – will add it to the bucket list.

Wonderful ideas for our future road trips!

We have only visited the Pictured Rocks, and Tahquamenon Falls (from your list) while having a road trip around Lake Huron, few years ago. Upper Michigan is a beautiful area, we love it!

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9 Best Road Trips to Take in Illinois

Illinois , often known for its large cities like Chicago, has much more to offer for those seeking a scenic and historical road trip. Stretching from the Great Lakes to the Mississippi River, Illinois has a variety of landscapes, from rolling farmlands and dense forests to winding rivers and ancient mounds. Its history, deeply tied to the rivers that border and cross it, along with its role as a major transportation hub, has left the state dotted with landmarks that span centuries. From the prehistoric civilizations at Cahokia Mounds to the historic significance of Route 66, these are the nine top road trips to take in the Prairie State.

The Great River Road

The Great River Road in Illinois is part of a much larger route that follows the Mississippi River from its headwaters in Minnesota down to the Gulf of Mexico . The Illinois portion begins at the state’s northern border near East Dubuque and winds its way south to the junction with the Missouri border near Cairo. This picturesque drive spans roughly 550 miles, tracing the river's path and offering a direct connection to nature and small-town life along the Mississippi River. It’s a journey that typically takes two to three days, depending on how long you spend exploring each stop along the way.

Galena is an essential stop, home to the Ulysses S. Grant Home and a well-preserved 19th-century downtown along the Galena River. Further south, Pere Marquette State Park near Grafton has striking overlooks and hiking trails at the confluence of the Illinois and Mississippi Rivers. Cairo, once a vital river town, is the place where you'll find the Customs House Museum and Fort Defiance Park, where the Mississippi River and Ohio River meet.

Route 66 Scenic Byway

The Illinois stretch of Route 66 , the "Mother Road," runs from Chicago to St. Louis , spanning approximately 300 miles. It’s a journey through nostalgia, with stops at roadside diners, quirky museums, and landmarks that evoke mid-century Americana. This route offers a deep dive into the culture and history of the American road trip, with attractions that span decades of automotive and cultural history.

Pontiac is a key stop, home to the Route 66 Hall of Fame and Museum, where murals and exhibits celebrate the highway’s history. In Litchfield, the Ariston Café, one of the oldest restaurants along Route 66, serves as a living monument to the road's culture, while the Litchfield Museum adds context to the town's connection to the highway. At the end of the Illinois journey, the Chain of Rocks Bridge is a unique perspective on Route 66, with its famous bend over the Mississippi River and views of the St. Louis skyline.

Starved Rock State Park Road Trip

Starved Rock State Park entrance, Illinois. Editorial credit: Sanya Kushak / Shutterstock.com

A road trip to Starved Rock State Park typically begins in the Chicagoland area and spans roughly 100 miles west to the park near Utica, Illinois. Known for its dramatic canyons, waterfalls, and hiking trails, Starved Rock is one of Illinois’ most popular outdoor destinations. The trip is an ideal mix of nature, history, and small-town vibes. It’s a perfect weekend getaway that immerses travelers in the natural beauty of Illinois.

Stop at Matthiessen State Park for a taste of the region’s canyons and waterfalls, with its less-crowded Dells area providing a peaceful alternative to the more popular Starved Rock. Just outside the park, the town of Utica is worth a visit for its local charm and history, including the LaSalle County Historical Museum and its connection to the Illinois and Michigan Canal. Starved Rock itself is the trip's centerpiece, with 13 miles of trails winding through glacially-carved canyons, leading to waterfalls like those in French Canyon and impressive overlooks such as Lover’s Leap.

The Lincoln Highway

The Lincoln Highway in Illinois runs 179 miles from the Indiana border near Lynwood to the Iowa state line at Fulton. As the first transcontinental highway, it played a crucial role in connecting small towns across the country. Driving this stretch gives travelers a sense of early 20th-century American road travel and highlights key historical towns along the way, making it a meaningful journey for history enthusiasts and road trip lovers alike.

A quaint stop is Dixon, home to the Ronald Reagan Boyhood Home, where visitors can explore the early life of the former president. Ashton has a unique Lincoln Highway interpretive site with its iconic “Gazebo,” where travelers can learn about the road’s impact on local communities. Finally, Fulton’s Dutch Windmill and Riverfront Park are a historical endpoint at the Mississippi River, connecting the highway’s history with the region’s rich immigrant heritage.

Meeting of the Great Rivers Scenic Byway

The Meeting of the Great Rivers Scenic Byway spans 33 miles along the Mississippi River, Missouri River , and Illinois River , beginning in Alton and stretching to Pere Marquette State Park. This route follows the natural river systems that have shaped Illinois’ landscape.

A must-see stop is the Lewis and Clark State Historic Site in Hartford, where visitors can explore the replica of Camp River Dubois, the starting point of the explorers' journey. Grafton has a charming river town atmosphere, with opportunities for riverboat cruises at Grafton Harbor to experience the convergence of the rivers firsthand. Another important stop is the National Great Rivers Museum in East Alton, which highlights the engineering and environmental impact of the Mississippi River through interactive exhibits and a guided tour of the adjacent Melvin Price Locks and Dam.

Ohio River Scenic Byway

The Ohio River Scenic Byway runs 188 miles along Illinois’ southeastern border, from New Haven to Cairo, following the path of the Ohio River . This route shows a glimpse into early American commerce and the role the river played in shaping both the economic and cultural history of the region. The byway connects small towns that were once vital to river trade, making it a drive rich in historical significance.

Key stops include Cave-in-Rock State Park, where travelers can explore the massive cave that once served as a hideout for river pirates. Elizabethtown’s Rose Hotel, built in 1830, is a window into 19th-century river travel, and we recommend you take a walk through its historic district. Another notable stop is Fort Massac State Park in Metropolis, where visitors can explore a reconstructed 1802 fort. It looks into the region’s military history and its strategic location along the Ohio River.

Cahokia Mounds Road Trip

The Cahokia Mounds road trip begins in Collinsville, Illinois, and takes travelers through the heart of one of the largest prehistoric Native American civilizations north of Mexico. The Cahokia Mounds State Historic Site spans over 2,200 acres and contains 80 remaining mounds from the original city, which was at its peak around 1100 AD. This road trip is an opportunity to explore the remnants of this advanced society and gain insights into its archaeological significance, all within the boundaries of Illinois.

An intriguing stop is Monks Mound, the largest earthen structure in North America, towering 100 feet and boasting panoramic views of the site. The Interpretive Center, another key feature, presents exhibits, dioramas, and artifacts that illuminate the daily lives and achievements of the Cahokian people. Finally, a visit to Woodhenge, a reconstructed solar calendar, shows how the Cahokians tracked astronomical events.

Shawnee National Forest Scenic Drive

The Shawnee National Forest Scenic Drive is a network of routes winding through the southernmost part of Illinois, primarily along highways like Routes 45, 145, and 146, but it does not follow a single road. This drive typically begins in Harrisburg, Illinois, and ends near the town of Elizabethtown, covering over 280,000 acres of diverse forestland between the Mississippi and Ohio Rivers. The route showcases the natural beauty of the Shawnee National Forest, passing through dense woods, rock formations, and quiet rural areas.

One important stop along the drive is the Garden of the Gods Observation Trail, where visitors can walk among sandstone formations that have been shaped by millions of years of erosion. Another important stop is at the Bell Smith Springs Recreation Area, where hikers can explore a series of deep canyons, natural stone bridges, and springs. Lastly, Rim Rock Trail is another chance to delve into the forest’s diverse geological features, leading visitors through bluffs and into cool, shaded woodlands.

Illinois Covered Bridges Road Trip

An Illinois Covered Bridges Road Trip typically starts in the town of Chatham and ends in Princeton, taking travelers through the countryside of central Illinois. This route connects several historic covered bridges that date back to the 19th century, each with a well-preserved look into early American craftsmanship. The trip covers a large portion of the state’s rural landscape, making it ideal for those looking to explore Illinois’ history while enjoying a peaceful drive through the countryside.

An interesting stop is the Sugar Creek Covered Bridge near Chatham, built in 1880 and spanning 60 feet across the creek. The Cumberland County Covered Bridge, another key stop, was originally built in 1886 and later reconstructed. It is a picturesque setting for photos and exploration. A stop at the Red Covered Bridge in Princeton is where you want to go to see one of the state’s oldest covered bridges, dating back to 1863, and to enjoy the surrounding countryside that has changed little since the bridge’s construction.

Explore Illinois, One Road Trip at a Time

Whether you're interested in exploring Illinois' nature, historical significance, or a bit of both, there’s a road trip for everyone. The Great River Road offers a sweeping 550-mile journey along the Mississippi River, where you can experience the charm of towns like Galena and the historical importance of river commerce in Cairo. For those more nostalgic for the golden age of American road trips, Route 66 takes you on a journey through mid-century Americana, with quirky museums, roadside diners, and iconic landmarks. Lastly, if you're seeking an escape into nature, the Starved Rock State Park Road Trip immerses you in dramatic canyons, waterfalls, and the quaint town of Utica. Each road trip in Illinois invites travelers to discover the diverse stories that have shaped the state, from its ancient past to its role in modern American history.

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Chicago Memorial Day road, air travel expected to be its busiest in nearly 20 years

Thursday and friday are expected to be the busiest travel day in chicago, both on the roads and at airports, by staff and wire reports • published may 23, 2024 • updated on may 23, 2024 at 9:38 am.

Traveling for Memorial Day? Buckle up, Chicago, and prepare for busy roads and airports.

According to the Federal Aviation Administration, Memorial Day travel this year will be at its busiest since 2010, with more than 53,000 flights nationwide Thursday and more than 50,000 flights Friday.

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At O'Hare International Airport, more than 1.38 million passengers are expected to pass through the airport through Tuesday, the Chicago Department of Aviation said. At Midway, carriers project more than 294,000 passengers during the same time period.

Friday is expected to be the busiest travel day at both Chicago airports, the CDA said, while Thursday is expected to be the busiest nationally, the FAA said.

“This summer travel season is set to be our busiest in years, and O’Hare and Midway are ready to welcome travelers from all over the globe to Chicago," CDA Commissioner Jamie L. Rhee said in a release.

TSA predicts it will screen more than 18 million travelers and airline crew members during the seven-day stretch that begins Thursday, up 6.4% from last year.

“We’re going to break those records this summer,” TSA Administrator David Pekoske said.

American’s chief operating officer, David Seymour, said the airline has beefed up its staffing and technology in preparation for the seasonal rush.

“It’s a long summer, but we’re ready for it. We have the right resources,” he said.

Chicago-based United Airlines is forecasting its biggest Memorial Day weekend, with nearly 10% more passengers than last year. Delta Air Lines expects to carry 5% more passengers this weekend, kicking off its heaviest summer schedule ever of international flights.

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As of 5:30 a.m. Thursday, there were only three cancellations at O'Hare, and two at Midway, according to tracking site FlyChicago . Average delays at both airports were less than 15 minutes, the site showed.

For those planning a road trip, more than 38.4 million people across the country will be joining you, AAA said. Approximately two million of those people will be traveling across Illinois.

According to AAA, its the "most road trips" the agency has ever seen for Memorial Day.

“We haven’t seen Memorial Day weekend travel numbers like these in almost 20 years,” AAA Travel senior vice president Paula Twidale said in a release. "We’re projecting an additional one million travelers this holiday weekend compared to 2019, which not only means we’re exceeding pre-pandemic levels but also signals a very busy summer travel season ahead.”

Transportation data and insights website INRIX noted that drivers leaving Thursday or Friday should plan to hit the road early "to avoid mixing with commuters."

"Travelers going back home on Sunday or Monday should avoid the afternoon hours when return trips will peak," INRIX added.

Overall, travel is expected to be up to 90 percent longer than normal, INRIX said, and Chicago will be one of the most congested metro areas.

According to INREX, Milwaukee to Chicago via I-94 E is predicted to be at "peak congestion" around 4:30 p.m. Sunday. That trip is expected to take approximately two hours and 25 minutes, which is roughly 27% longer than usual, INREX said.

Best and Worst Times to Travel by Car Over Memorial Day

According to INRIX, here are the best and worst times to travel by car over the holiday:

Costco, Target, Aldi: What's open and closed on Memorial Day 2024?

REAL ID in Illinois: Why you'll soon need a different form of ID to board a plane in the US

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