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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. 

chicago road trip

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!

road trips from 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.

best road trips USA

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.

Chicago road trips

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.

Road adventures Lake Michigan

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!

Chicago days out

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.

Chicago road trips

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.

Chicago road trip adventures

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.

Chicago road trip

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.

Boyne Mountain Chicago

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: . 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?

chicago road trip

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.

Road trips from Chicago

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.

Road trips through chicago

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!

best road trips starting in chicago

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.

Road trip in Chicago

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.

driving 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.

Day trips from Chicago

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!

Huron-Manistee National Forest

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.

VickyFlipFlop up the Skydeck

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

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.

Photograph: Shutterstock

Lindsay Eanet

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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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Make a quick escape and spend a few nights amidst nature. 

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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.

Sunrise in Sheboygan Wisconsin from my balcony at Blue Harbor Resort

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!

Sign marking the beginning of Route 66, which is one the best road trips from Chicago you can possibly take

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.

Old rusty car that says LA to Chicago on back. Sitting in a field with grass growing around it

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

Elgin History Museum is one of the many reasons Elgin is a good road trip from Chicago

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).

Historic home in Elgin Historic District

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.

Outside of Emmett’s Brewing Co in West Dundee Illinois

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,

Indiana Dunes National Park, Indiana

best road trips starting in chicago

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,

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Round Barn Winery in Southwest Michigan, one of many wineries in Harbor Country

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.

Sculpture with lighthouse in the background at Silver Beach in Saint Joseph, Michigan in Harbor Country

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,

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha Wisconsin frame and lighthouse with Lake Michigan on the horizon. Kenosha is one of many great road trips from Chicago.

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.

Carthage Institute of Paleontology and the Dinosaur Discovery Museum in Kenosha Wisconsin

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,

McHenry County, Illinois

Driving time: 1 hour 30 minutes

Gorgeous pond with lily pads and picturesque bridge at Fel-Pro RRR

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.

Sundae at Julie Ann's Frozen Custard with their signature ice cream truck in the background

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.

Cherry Tree Inn Bed and Breakfast in McHenry County Illinois, where Bill Murray's character stayed in Groundhog Day

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,

Starved Rock State Park

Waterfall in 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

Exterior of Lincoln-Tallman House in Janesville Wisconsin, a must-see when you take a road trip from Chicago

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.

Devil's Staircase on Wisconsin's Ice Age Trail in Janesville

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.

Holiday Light Show at Rotary Botanical Gardens in Janesville Wisconsin

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.

best road trips starting in chicago

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,

Lake Geneva, Wisconsin

Yerkes Observatory in 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.

Mansions on Geneva Lake seen from the mailboat tour

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 .

Black Point Estate on Geneva Lake, an historic mansion with many ties to Chicago.

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,

Milwaukee, Wisconsin

Harley Davidson Museum entrance - one of the many things to do in Milwaukee, an easy road trip from Chicago.

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,

Lafayette, Indiana

Driving time: 2 hours

Haan Mansion Museum of Indiana Art

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.

SAMARA in West Lafayette, Indiana

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,

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

Blue Gate Restaurant in Shipshewana, Indiana, with man-made pond and bushes in foreground and people outside.

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,

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.

Learning how to sail in Sheboygan Wisconsin

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.

A squirrel sits on top of a sculpture of a gnome playing a cello, part of the James Tellen Woodland Sculpture Garden near Sheboygan, Wisconsin

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,

Elkhart Lake, Wisconsin

Dock extending into Elkhart Lake at sunset

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

Historic downtown Galena, Illinois

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.

Long Hollow Canopy Tours in Galena Illinois near Eagle Ridge Resort

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,

Hendricks County, Indiana

Pond at Natural Valley Ranch in Hendricks County Indiana, an easy road trip from Chicago

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,

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

Columbia Street at The Landing in Fort Wayne

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.

Reenactors at Old Historic Fort Wayne

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.

Burrata at Birdie's in Fort Wayne Indiana

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,

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

Captain's Walk Winery in Green Bay Wisconsin

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.

best road trips starting in chicago

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

View of downtown Dubuque Iowa from the top of the Fenelon Place Elevator

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.

Julien Dubuque Monument at the Mines of Spain State Recreation Area in Dubuque Iowa

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.

The world's shortest steepest railroad is the Fenelon Place Elevator in Dubuque Iowa

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.

Lobby of Hotel Julien Dubuque

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,

Brown County, Indiana

Driving time: 4 hours

Brown County Playhouse

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,

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Taking a tour with Sandusky Segwave is a great way to explore Sandusky, Ohio. In this photo, the tour director is pointing out something of interest in a city park.

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.

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 .

Lake Erie Cookie Island Monster at Dipper Dan's 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,

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

Illinois Route 66 sign with the L tracks in the background

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!

Hit the road with dozens of road trips from Chicago. Photo is of a Segway tour in Sandusky, Ohio on the bottom and downtown Galena, Illinois, on the top.

Dang Travelers


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.

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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

best road trips starting in chicago


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!

The top picture is a sweeping view of a valley filled with trees with fall color in Porcupine Mountains Wilderness State Park and the bottom is a lake in Illinois with cypress trees that have orange and green leaves with a text overlay that says the best road trips from Chicago.

  • 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 Time to Visit the Galápagos Islands - June 26, 2024
  • Top 10 Best Things to Do in Banff National Park - June 20, 2024
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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.

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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10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

  • Milwaukee, Wisconsin (1 hour, 30 minutes)
  • Madison, Wisconsin (2 hours, 25 minutes)
  • Grand Rapids, Michigan (2 hours, 47 minutes)
  • Peoria, Illinois (2 hours, 41 minutes)
  • South Bend, Indiana (1 hour, 39 minutes)
  • Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

  • Distance: An hour by car
  • Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

  • Distance: An hour and a quarter by car
  • Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

  • Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

  • Distance: An hour and a half by car
  • Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

  • Distance: An hour and forty minutes by car
  • Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

  • Distance: Around three hours by car
  • Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

  • Distance: Three hours by car
  • Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor university

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

  • Distance: Around three hours and 45 minutes by car
  • Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

  • Distance: Four and a half hours by car
  • Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Fall colors in Traverse City

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

  • Distance: Five hours by car
  • Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

  • Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
  • Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
  • Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
  • Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

The Santiago Calatrava-designed Margaret Hunt Hill Bridge spans Dallas’ Trinity River.

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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 road trip from chicago

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

starved rock state park from chicago

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 500

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

galena roadtrip from chicago

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

Indiana Dunes National Park from Chicago

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

Frederik Meijer Gardens Sculpture Park

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

monona terrace madison wi

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 road trip from chicago

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 state park 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

Wisconsin Dells Road Trip from Chicago

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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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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Your Family Will Love These 30 Road Trips Near Chicago

  • Updated: 04/03/2024

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

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 .

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Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of

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

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

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 .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of

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

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 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.

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 more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI “

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

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

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

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

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

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

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

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. 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 . 

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.

Janice Moskoff in front of doorway in Valletta, Malta. (Credit: Danielle Cassar)

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 . Check out  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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best road trips starting in chicago

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

best road trips starting in chicago

The Meramec Caverns have rich human history as well

best road trips starting in chicago

Monstrocity , photo by Laurie Skriva, [email protected]

best road trips starting in chicago

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.

IMG-20180902-WA0028 (1)

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.

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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.

Pensacola beach

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.

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2 responses to “14 summer road trip ideas from chicago (updated for 2024)”.

wnctravel Avatar

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.

Amit Sharma Avatar

Thanks for the suggestion for Middleboro, KY – will add it to the bucket list.

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Hiking And Camping Road Trip From Chicago To Devil’s Lake State Park, Wisconsin

Hiking And Camping Road Trip From Chicago To Devil’s Lake State Park, Wisconsin

How To Plan A Perfect Road Trip?

How To Plan A Perfect Road Trip?

Best Fall Color Road Trips From Chicago

Best Fall Color Road Trips From Chicago

Summer Picnic – Gilson Park Beach And Bahai Temple Combo At Wilmette

Summer Picnic – Gilson Park Beach And Bahai Temple Combo At Wilmette

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12 Super Road Trip Destinations from Chicago for Spring Break

Sunday, january 23, 2022.

12 Super Road Trip Destinations from Chicago for Spring Break

12 Super Road Trip Destinations from Chicago Perfect for Your Next Adventure

With warmer days hopefully upon us soon, time is here to think about road trips! I am sharing a few of my favorites within a range of distances.  Happy trekking!

Within 3 Hours

Galena, Illinois: Downtown Galena enchants with one of the most beautiful historic districts in the USA. The bustling downtown full of shops, wineries, eateries and history beckons wanderers. Nearby hiking experiences are plentiful and treat to fantastic views of the Mississippi including from one of our favorites, Mississippi Palisades State Park . The Ulysses S. Grant is home is one of our favorites to tour and includes so many authentic family artifacts. While in Galena, wander over to nearby Dubuque, Iowa for a trip up the Fenelon Place Elevator. 

Madison, Wisconsin: Wisconsin's state capitol, Madison , unfolds an amazing opportunity for a family getaway. The Wisconsin State Capitol Building is striking and quite an interesting place to tour. Don't forget to step out on one of the balconies for a view. A plethora of hiking opportunities exist in and around the city including Lakeshore Nature Preserve, Blue Mound State Park, Devil's Staircase and Pheasant Branch Conservancy. Olbrich Botanical Gardens enchants in all seasons. Chazen Museum of Art, Madison Children's Museum and Wisconsin History Museum all add to any itinerary. We also love nibbling at the bakeries in Madison including Madison Sourdough and Batch Bakehouse. 

Quad Cities, Illinois and Iowa: The Quad Cities incorporates a number of Illinois and Iowa communities saddling the striking Mississippi River. A wealth of nature activities can be enjoyed including hiking and bird watching on Sylvan Island, at Black Hawk Historic Site, at Illiniwek Forest Preserve and more. Putnam Museum and Science Center, Figge Art Museum and Quad Cities Botanical Center offer more avenues of discovery. Don't forget to pick up ice cream at Whitey's or Lagomarcino's. For the over 21 crowd, hit the Quad Cities Ale Trail. We love the wealth of activities available and return to the Quad Cities again and again!

Within 6 Hours

Columbus, Ohio: Columbus has been one of our favorite cities to wander. We love German Village full of historic buildings and small businesses. Visiting Schmidt's Restaurant rewards with fabulous and authentic German fare. (My favorite is the German chocolate pie.) Museums include the Center of Science and Industry with a dinosaur gallery, Columbus Museum of Art and Central Ohio Fire Museum. We also enjoy visiting the Columbus Zoo and Aquarium which has one of the best African savanna experiences I have viewed.

Grand Rapids, Michigan:   Grand Rapids is home to one of my favorite botanical gardens and sculpture parks, Frederik Meijer Gardens & Sculpture Park. the grand scale sculptures are breathtaking and the gardens awe especially the Japanese garden. We also find the Grand Rapids Public Museum and Grand Rapids Art Museum fascinating. We usually pair a trip to Grand Rapids with a trip to Lake Michigan's shore often at Grand Haven. I am totally a beach lover in all seasons and often prefer spring for visits because there are fewer visitors. Rosy Mound Natural Trail in Grand Haven is one of our cherished nature highlights.

Hocking Hills, Ohio: Hocking Hills State Park in Ohio fascinates with a cache of unique hikes exploring canyons, caves, cliffs, waterfalls and much more. We love renting a cabin in the region for a little nature respite away from it all.

Louisville, Kentucky:   Louisville offers a great launching point for a Kentucky vacation. Museums including the Louisville Slugger Museum & Factory and Frazier History Museum present venues entertaining a range of interests. Churchill Downs is iconic. Louisville Mega Cavern bestows a venue for weaving through ropes courses and sliding along ziplines underground. The food scene includes so many of our favorites including Mark's Feed Store and Homemade Ice Cream and Pie Kitchen. The Camberly Brown and Seelbach hotels sweep you back to old hospitality. Of course, bourbon is a must for the 21+ crowd.

Shawnee National Forest: Shawnee National Forest in Southern Illinois welcomes travelers to unique hikes with unparalleled views. The forest includes a remarkable 289,000 acres of nature adventures to experience. Hiking, camping, horseback riding, biking, fishing, climbing, boating and more forge incredible nature experiences in some of the most unique settings of the Midwest.

St. Louis, Missouri:   St. Louis is an ideal location for a little getaway right along the mighty Mississippi River. The City Museum, St. Louis Science Center, St. Louis Zoo and St. Louis Art Museum among others inspire discovery. Of course, visitors must check out the Gateway Arch! Eating on 'The Hill' will treat you to fantastic Italian fare. You will also be near Cahokia Mounds where you can learn about the Mississippian Mound Builders. Additionally, you can head to St. Charles or Ste. Genevieve for a little French colonial history. When in St. Louis, one must also take an Anheuser-Busch Brewery Tour.  So many avenues of exploration make St. Louis a fabulous destination.

Within 8 Hours

Minneapolis and Saint Paul, Minnesota:   Minneapolis and Saint Paul have always been a favorite locale to visit. I love that there are spaces to admire nature right in Minneapolis and St. Paul including Minnehaha Falls, Chain of Lakes and Shadow Falls. Plus, there are tons of hiking opportunities nearby in Minnesota and Wisconsin. Mill City Museum and the Museum of Russian Art are two of my favorite museums in the Midwest. A walk along the Stone Arch Bridge and a peek at flour mill ruins provide an interesting look at Minneapolis. Como Zoo Conservatory in nearby Roseville treats to magnificent floral displays in all seasons. The region is populated with local microbrews adding tasting experiences.

best road trips starting in chicago

Omaha, Nebraska: Perched along the Missouri River, Omaha offered us a wonderful starting point for a few nature adventures including Platte River State Park, Lewis and Clark Monument Park, Heron Haven and more. We loved walking around the Old Market, peeking into the Passageway and more. The city includes a wealth of museums such as the Durham Museum, Joslyn Art Museum, Omaha Children's Museum present a wealth of adventures.  For a truly unique scene, visit Hollywood Candy which not only delights with tons and tons of candy but includes a vintage pinball arcade, movie memorabilia, a '50s diner, vinyls and so much more!

Pittsburgh, Pennsylvania: Pittsburgh is a fantastic vacation choice for any season. The city's range of museums inspires any wanderer. The National Aviary is a wonder that should not be missed. Several rooms are free-fly, so you will have all sorts of interesting birds freely flying and roaming. Andy Warhol Museum, Heinz History Center, Carnegie Museum of Natural History and more will invite exploration. Don't forget to take the Duquesne Incline up to the top of Mount Washington for a view. We have to take in this view EVERY time we are in the city. Wander the Strip District for all sorts of foodie treats and shops. Hiking, river views and more will entice nature lovers. Every trip to Pittsburgh welcomes us to new experiences.

12 Super Road Trip Destinations from Chicago Perfect for Your Next Adventure

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best road trips starting in chicago

The Best Road Trips From Chicago To Take This Spring

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.

Tori Levy

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

Madison, Wisconsin, USA downtown skyline at dusk on Lake Monona.

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

Windmill in Holland Michigan - An authentic wooden windmill from the Netherlands rises behind a field of tulips in Holland Michigan at Springtime.

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

fall foliage surrounding Downtown Traverse City Michigan with a lake in the background

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

St. Louis, Missouri, USA downtown cityscape on the river at dusk.

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

iew of Kirkwood Street across from the college campus of Indiana University Bloomington (IU), a major public research university located in the US midwest.

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

Columbus, Ohio, USA skyline on the Scioto River with tall buildings and green grass

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

downtown of the Wisconsin Dells, which is a major tourist attraction in the US state of 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

Sunset over the water on Lake Michigan at Saugatuck Michigan

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

Historic Michigan Theater, built in 1928, located on East Liberty St in Downtown, Ann Arbor

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

Beautiful walkway through the natural sand dunes along the Great Lake shores. The Kohler Andrea park is in the area around Sheboygan and Wilson Wisconsin. Small trees and Juniper bushes along path.

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

Cityscape of Cincinnati's Roebling bridge.

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

best road trips starting in chicago


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15 Ultimate Road Trips from Chicago

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


best road trips starting in chicago

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

road trips from chicago- starved-rock

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

indiana dunes park- road trips from chicago

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

lake geneva

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.

balloon race-road trips from chicago

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

Saugatuck- road trips from chicago

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

wisconsin state capitol

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

lighthouse road trips from chicago

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

woolen mill-cedarburg

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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best road trips starting in chicago

From the Editor

Midwest travel.

My name is Christine Zwolinski and I'm your mom friend around town. I live in chicago with my husband manny and two children, Noah and Mila!

best road trips starting in chicago

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Great Road Trips from Chicago this Spring!

March 12, 2024.

Road trip season is officially here! Here is a list of great Chicago road trips you can do a day or long weekend. Many of these make family trips and a weekend couples trip, all 6 hours or less from Chicago.

If you are looking for some road trip essentials like travel pool toys and things to keep kids entertained on trips, you can see my shopping guide here !

Mall of America, Bloomington, Minnesota

Although this might be a short flight away, I know many people who have driven it. We just did Mall of America in Minnesota and it’s like Vegas – but for kids. There is SO much to do. Not only is there the Nickelodeon Universe, there are lots of other attractions like Sea Life (the underwater 360 tunnel is really cool), Crayola experience (great for younger kids), Lego attraction, Flyover America, and more. There are hotels connected to the mall – JW Marriott and Radisson Blu. We stayed at the JW and it was great, plus they have an indoor pool. You can see my reel here of some of the things we did! 

best road trips starting in chicago

Galena, Illinois

One of our most favorite getaways is Galena ! It’s great for families, a romantic getaway, or a relaxing girls’ weekend. This charming southwestern Illinois city is an easy drive – just a little over 3 hours from Chicago.

  • Grab a coffee at Trolley Depot Coffee & Tea and take the trolley on a scenic, historic tour of Galena where you’ll see many of the original early nineteenth-century buildings.
  • You can do yoga with or take a walk with goats, and then shop the small boutiques & cafes that line the main streets.
  • I love Bread and Vine or Otto’s for breakfast, brunch, or lunch.
  • Durty Gurt’s for lunch or dinner.
  • Stroll to Isabella Ltd for beautiful gifts & home decor.
  • Check out Poopsies for the ultimate toy store.

If you’re a golfer and/or want to get away from the hustle and bustle, I recommend staying at the sprawling Eagle Ridge Resort & Spa. It is a bit of a drive to Main Street, so if the majority of your plans center around shopping and dining, I would suggest staying closer to town!

The Irish Cottage Inn & Suites is a boutique hotel about 3 minutes from downtown with friendly staff, onsite dining, and has been recently renovated. There are also plenty of AirBnb’s to choose from right on the main strip.

best road trips starting in chicago

Sheboygan, Wisconsin

Sheboygan is a lake resort town, where a summer stay is the star but with an indoor water park at Blue Harbor Resort, it’s the perfect all-season getaway! The resort also has mini golf, an arcade, outdoor swimming, nightly campfires, and beaches. Stay in the hotel for easy access to the amenities and restaurants, or get a villa down the beachside with your own kitchen, living room, and multiple bedrooms. Sheboygan is great for families, girls’ getaways, and couple trips. If you’re traveling with younger children, Bookworm Gardens is a must-see. And, definitely make sure you eat at Field to Fork Cafe !

Milwaukee, Wisconsin

Milwaukee is incredibly close to Chicago which makes it an easy day trip! MKE serves up great restaurants with lots of shopping! You can brewery hop or walk around downtown. Visit Broadway Paper (paper and gift store) and MOD GEN (gorgeous plants), and then brunch at the popular and delicious Sweetdiner ! This can be done in a day or stay for the weekend! I’ve taken the Amtrak there and it’s such an easy ride!

best road trips starting in chicago

Starved Rock, Illinois

I recently went to Starved Rock, Illinois, and had the best time! It is about 2 hours away from Chicago and a pretty easy road trip! It’s great for hiking with or without the kids. However, I would recommend taking older kids because part of the trail is pretty difficult. It took about one hour each way to complete one hike. Then, there is a restaurant we grabbed lunch at on the top of Starved Rock. It was pretty good and had pretty views of the canyon!

best road trips starting in chicago

 Oregon, Illinois

We took a family road trip to Oregon, Illinois three years ago and stayed at @pinecreekescape cabins. cabins. These are log cabins across from White Pines State Park. Check out the Bison at Nachusa Grasslands where you can see Bison roam free. It’s pretty cool! Or hike the White Pines State Park, which has beautiful hiking paths and a playground for the kids. We picked up steaks from a local butcher and grilled them that night along a campfire. If you are looking to get outside and be one with nature, this is the trip for you!

best road trips starting in chicago

Rockford, IL

Rockford, Illinois is just about 100 miles northwest of Chicago. We love to stroll through and see the 12 acres of gardens, waterfalls, ponds, and tea house at the Anderson Japanese Gardens. When you’re ready to fill your belly, head over to The Norwegian, which is only a 3-minute drive from the Gardens. They serve delicious drinks, brunch, and dinner in the summer. Don’t skip the Danish pancake balls and homemade jam! Walk off your meal and shop next door at the cutest mid-century modern shop, Rooted, for gifts and home decor. 

If the weather is good and you’re there on a weekend, check out The Top Rooftop Bar & Lounge at Embassy Suites for views of the historical downtown, drinks, and apps! If you’re visiting with kids, make sure to check out Discovery Center Museum for a totally fun, interactive experience.

best road trips starting in chicago

Lake Geneva, Wisconsin

Lake Geneva is a popular lake town with so much to do! There are magic shows for tweens+, a historical museum, boat and jet ski rentals, boat tours (the mailboat is particularly cool), a skate park, a disc golf course, a safari(!), and golfing galore. The water park at Timber Ridge, @timberridgelodge , part of @grand_geneva , is great for littles! You can also take a walk or bike ride by the lake and then grab something yummy at one of the downtown restaurants. 

Saugatuck, Michigan

One of my favorite road trips is to Saugatuck, Michigan! It’s about 3 hours away from Chicago and there is so much to do! There are dune rides, great restaurants, beaches, ferry ride shops, & art galleries! I have two full blog posts here – for families or a couples trip to the area.

best road trips starting in chicago

New Buffalo, Michigan

Roughly 90 minutes from Chicago, New Buffalo, Michigan is a super fast drive and you can stay the day or the weekend. Public beach, small shops, coffee shops, wine trail (almost all but 1 allow kids), check out some breweries in the area, hike the dunes or Galien River, etc. There’s a full blog post here .

best road trips starting in chicago

Holland, Michigan

Lastly, is Holland, Michigan . It’s just the cutest little town! There’s so much to see and do between the dunes, the beach, the tulips, and the windmills! Downtown Holland has many great restaurants and shops. Don’t miss Lemonjello’s for college shop vibes, coffee and pastries, The Holland Peanut Store, an old-school candy shop, Neli’s Dutch Village , a Netherlands theme park with a great gift shop, and Deboer Bakery for amazing cronuts. For dinner, we love New Holland Brewery , Boatwerks (the only waterfront restaurant in town), and Beechwood Grill.

best road trips starting in chicago

Hopefully, some of these road trip ideas from Chicago will be helpful! Let me know if you travel to any of these great Midwestern cities or tell me where I should go next!

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  • Destinations

12 Best Road Trips From Chicago

Are you looking for where you should go on a road trip from Chicago?

Chicago is a city of towering skyscrapers, ever-enthusiastic sports fans, thumping music festivals, and cultural richness. While there is a constant juggling of things and adventure activities in Chicago which will keep you occupied. The city is in a prime spot with a lot of road trip options for you to escape to the surrounding destinations within 5 hrs drive. No need to get on the flight. Drive, reach and enjoy the beautiful states around.

So if you are already in Chicago then you should explore these 12 best road trips from Chicago.

1. Geneva, Illinois - 41.7 miles

explore Geneva

Looking for a quick and short road trip from Chicago? The uniquely, charming town is within an hour ride from Chicago. Lining the face of the city are tons of amazing shops, gourmet restaurants, and tree-shaded streets, adding to the beautiful weather and the character of the place. Have a relaxing day at the Fabyan Forest Preserve, indulge in the activities at Peck Farm Park, and take a tour of the Fabyan Villa Museum & Geneva History Museum.

Geneva is one of the popular day trips from Chicago.

Time Taken: 49 minutes approximately

2. Indiana Dunes National Lakeshore, Indiana - 51.9 miles

 Indiana Dunes National Lakeshore

Considered as one of the top places to visit near Chicago in summer, Indiana Dunes National Lakeshore along with the park appeals to families who are looking for a picnic destination from Chicago. Hugging the Lake Michigan is the Indiana Dunes National Lakeshore with its rugged dunes, inviting pastures, and winding rivers, that offers plenty of activities based on the season.

Make a quick stop at the visitor's centers to grab the map of the area and gain info on the terrain.

Go hiking or hire a bike and ride through the trails, take up the Three Dune challenge to climb up the trees, and enjoy the mesmerizing view of the Lake.

Time Taken: 1 hour 2 minutes approximately

3. Harbor Country, Michigan - 72.9 miles

Harbor Country

A group of 8 small towns along the Eastern Shore of the Lake Michigan makes up the Harbor Country. Dotted with plenty of Bread & Breakfast places, beaches, and wineries along with its trademark geographic location, the upscale destination of Harbor Country is one of the popular weekend getaways near Chicago for couples. The tree-lined roads and the beachy feel will surely ease you.

Meander through the soft, sandy beaches decorated with dunes all the way, go on a wine-tasting spree by visiting all the famous local wineries, check out the modern art galleries, visit the theaters in the Three Oaks, and stack your bags with collectibles from antique shops.

Time Taken: 1 hour 13 minutes approximately

4. Lake Geneva, Wisconsin - 83 miles

Lake Geneva

Perched on top of the Geneva Lake, Lake Geneva is a resort city in Wisconsin that welcomes its tourists with its enchanting spas, charming B&Bs, and world-class golf resorts. With its amazing array of activities during the time of winter, Lake Geneva is one of the ideal road trips from Chicago in winter. But Lake Geneva doesn't stop just in winter, it is an all-season destination with activities, events, and wonders for every season.

Camp at the Big Foot Beach State Park, enjoy the history by going on a tour of the beautifully preserved Black Point Estate and Gardens, catch a mesmerizing sunset by the Geneva Lake, hike the Geneva Lake Shore Path, and book for a fantastic show at the Tristan Crist Magic Theatre. Time Taken: 1 hour 26 minutes approximately

5. Milwaukee, Wisconsin - 92.1 miles


Nicknamed the 'Cream City ' for its attractive cream-colored bricks and 'Brew City' for its rich brewing history, Milwaukee is regarded as one of the last-minute weekend getaways from Chicago.

With its waterfront location and its fabulous architecture in place, Milwaukee successfully retains its small big-city like appeal attracting visitors from Chicago on a constant basis. The warmth and the culture in Milwaukee Illinois make it distinctive.

Visit the Discovery World along with your family and kids, understand history at Milwaukee Public Museum, go through the works of art at Milwaukee Art Museum, get a flavor of Pabst Theater, and experience Mitchell Park Horticultural Conservatory & Milwaukee County Zoo.

For motorcycle lovers, a visit to the Harley-Davidson Museum is highly recommended. Time Taken: 1 hour 28 minutes approximately

6. Starved Rock State Park, Illinois - 99.7 miles

best road trips starting in chicago

Rated as one of the most beautiful attractions and top places to visit in Illinois, Starved Rock State Park is a class apart!

Characterized by dozens of canyons within the park ground, Starved Rock State Park attracts over 2 million visitors annually which is a testimony to its popularity and for a complete experience of the place, stay at the logged wooden cabins is a must.

Witness the beauty of the amazing waterfalls that are active in the time of spring and just after a rainfall, go hiking along the nature trails, and soak in the spectacular views.

With plenty of activities for everyone, Starved Rock State Park is one of the best day trips from Chicago with kids. Time Taken: 1 hour 37 minutes approximately

7. Saugatuck, Michigan - 141 miles


Part of the Arts and the Crafts movement of the late 19th century, Saugatuck is an arts colony and a tourist destination in Michigan that needs to be visited by the creators and art enthusiasts.

The fun little harbor village destination is literally charming and is the sweetest of destinations, ideal for a family trip. The laid-back medieval kind of atmosphere will be completely a relaxing experience.

Scan the lengths of the Saugatuck Dunes State Park, visit the Oval Beach Saugatuck on a sunny day and get tanned, go window shopping at the Butler Street, hike to the Mount Baldhead Park, and check out the art galleries.

Time Taken: 2 hours 14 minutes approximately

8. New Glarus, Wisconsin - 145 miles

New Glarus

Interested in getting the flavor of Switzerland in America? Go on a road trip to New Glarus from Chicago, America's Little Switzerland .

Known for its Swiss heritage, old-world architecture, ethnic dining experience, a craft brewery and Swiss-style chalets with flower-filled window boxes, New Glarus is America's Switzerland. Be prepared to hear a lot of yodeling and be on a watch out for the fiberglass cows decorated by the local artists.

Go on a picnic to the New Glarus Woods State Park, take on a guided tour of the New Glarus Historical Museum, get inside the Chalet of the Golden Fleece Museum, hike the Sugar River State Trail, and go wine tasting in the New Glarus Winery. Time Taken: 2 hours 27 minutes approximately

9. Galena, Illinois - 164 miles


Painted with rolling hills, scenically splendid roads, and historically charming sites, Galena is for those who are on a constant lookout for a simplistic location that will take them off their stressful routine offering them refreshment.

Have great fun at the Blaum Bros. Distilling Co, relax at the lush green Grant Park, go on a stroll across the Galena Main Street to shop at the art galleries and the antique store, spend a fun evening at the P.T. Murphy Magic Theater, and go on a exploration of US Grant Home Historic Site. Time Taken: 2 hours 44 minutes approximately

10. Grand Rapids, Michigan - 178 miles

best road trips starting in chicago

Nestled in a hilly, scenic location and easily accessible from Chicago, Grand Rapids in Michigan is renowned for its amazing culture, great food, and urban appeal.

Grand Rapids is named after the landmark river and the small town offers fascinating experiences that will make you think, it is a miniature version of Chicago where managing kids are comparatively easier.

Be amidst the Frederik Meijer Gardens during the spring and fall to enjoy the blooming flowers, take a guided tour of the Grand Rapids Public Museum, go on an adventurous journey to the John Ball Zoo, and make sure to check out the Gerald R. Ford Museum & Grand Rapids Art Museum. Time Taken: 2 hours 47 minutes approximately

11. Door County, Wisconsin - 244 miles

Door County Wisconsin

Adorned by a stunning coastline with the ever-changing leaves in the background, Door County is a popular vacation spot in Wisconsin that is dazzling with its natural beauty. Steeped deep in maritime heritage, Door County comprises plenty of maritime museums and lighthouses that add to the totally different atmosphere of the place.

Go on a sunrise walk along the lake, dive into the sweet delicacy of Montmorency cherries, explore Cave Point County Park on a kayak or drive along the winding roads surrounded by autumn colored trees, head to the Eagle Tower at Peninsula State Park for unparalleled views, and stuff your mouths with cherry-stuffed French toast. Time Taken: 3 hours 41 minutes approximately

12. Huron - Manistee National Forest, Michigan - 254 miles

best road trips starting in chicago

Extending along the peninsula of Michigan, Huron-Manistee National Forest comprises of several acres of land and the expansive grounds of Huron-Manistee National Forest has been a recreational area for the nature enthusiasts.

If you are a lover of nature and are interested in getting connected with nature and establishing a balance, then a picnic to Huron-Manistee National Forest is highly recommended.

Hike through the densely populated forest tracing your way through the trees, camp inside the parking area under the lights and have a peaceful sleep listening to the sweet lullabies of nature, unleash your fishing skills, and go canoeing along the rivers.

Time Taken: 3 hours 53 minutes approximately

Did we miss out on any of your favorite road trips from Chicago? Do let us know in the comments section.

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10 Road Trips From Chicago That Make Leaving The City Worth It


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Think Twice About Carrying Bear Spray This Summer

7 cutest small towns near denver in 2024, the cheapest month to visit las vegas (& budget tips).

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

Nashville, Tennessee, USA downtown city skyline on the Cumberland River.

12 Best Spring Break Road Trips from Chicago

Chicago is known for its world-class museums, including the Field Museum and the Museum of Science and Industry, but after the cold Chicago winter, most people will have exhausted the city's many indoor attractions. That makes spring break the perfect time to take a trip.

Whether you have a day, a weekend, or longer, there's a fabulous choice of spring break trips from Chicago. Drive to Cincinnati, Traverse City, Cleveland or Columbus, follow Scenic Route 61, or chase the sun south the Nashville, Hot Springs or Atlanta.

There's something for everyone in reach of Chicago, with great spring break road trips to suit if you're traveling with children, teens, or childfree. Keep reading to find out some of the best places you can get to from the Windy City this spring break.

Best spring break road trips from Chicago

Chicago makes a great place for a spring break staycation, and with its museums, parks and the attractions around Navy Pier to enjoy you might even be heading there as your main spring break destination. But if you're ready to explore a little further afield after the St Patrick's Day party, or looking for a day trip or two while you spend spring break in Chicago itself, you have some amazing destinations to choose from.

After the long winter, why not head out for an adventure when spring break rolls around again? We've listed some of our favorite spring break destinations, so keep on reading to decide what kind of trip awaits you this spring break.

If you're thinking of taking a road trip from Chicago in another season, check out our Best Road Trips from Chicago article for ideas and inspiration! We also have a detailed guide for traveling from Chicago in winter, if you want to plan ahead.

Day trips (about 3 hours each way)

Chicago sits proudly on the shore of Lake Michigan and is in easy reach of many other great Midwestern cities. That means that even if you're not looking for an overnight stay, you can still take an unforgettable spring break trip and be back home by evening.

1. Indianapolis, Indiana

3 hours 10 minutes from Chicago (180 miles)

Why you should visit: This is the shortest trip on the list, but there's plenty to see in the city whether you're traveling as a family with young kids or taking a break from college.

The Children's Museum is sure to be a hit for younger travelers – it's the world's largest children's museum. With a visit here your spring break can take you to modern Europe, ancient Egypt, or even into space.

Baseball fans might like to time the trip to catch the home opener of the Indianapolis Indians, which usually takes place in early April.

Indianapolis Children’s museum with models of dinosaurs

How to get there: Head out of Chicago on I-90 E then pick up I-65 which you'll follow south past Remington and Lafayette. After around 130 miles on the interstate you'll cross the White River to arrive in downtown Indianapolis.

Our highlights: The Indianapolis Children's Museum will definitely appeal to families on spring break. This huge space has engaging interactive exhibitions covering space travel, history, pop culture, science and technology, and dinosaurs.

Families and college athletes alike will also appreciate the NCAA Hall of Champions, which even has sports simulators where you can try your hand at new activities.

Elsewhere, Indianapolis Museum of Art blossoms in springtime when the thousands of bulbs planted at Newfields' gardens burst into life.

Indianapolis also has breweries, wineries and distilleries which you can visit with the Indy Craft Pass – something that might appeal if you want to party during spring break.

Bonus: You won't be able to see the famous Indy 500 automobile race during your spring break visit, as this usually takes place in May. If you decide to make a return trip to see the race, you'll be in good company – more than half a million people watch from around the Speedway.

Our travel tips: Weather can be variable during spring break, from 32 degrees F right up to 65 degrees. April is one of the wettest months of the year too, so pack accordingly.

2. Springfield, Illinois

3 hours 30 mins from Chicago (200 miles)

Why you should visit: This is a really easy drive out from Chicago, and with its presidential history it's a fascinating contrast to the Windy City. It's also a great place to spend a weekend, especially if you fancy following the Capital City Bourbon Journey.

Springfield is a great family getaway, especially if your kids have started to learn about the country's history.

You can immerse yourself in stories of the country's 16th President, Abraham Lincoln, who lived in the city for many years – his legacy as the country's Civil War-era president is sure to inspire grade schoolers and older teenagers alike, especially when you can visit the places where he lived and worked for real.

Abraham Lincoln Springfield House

How to get there: This is a really simple trip to navigate – just pick up I-55 S from your departure point in Chicago, and follow it all the way to Springfield, Illinois.

Our highlights: You could easily spend the whole trip exploring Lincoln-related sites. There's the Lincoln Home National Historic Site, where he lived until becoming President in 1861, and the unique, interactive Abraham Lincoln Presidential Library and Museum. You can also tour both the old and new state capitol buildings.

Younger kids will enjoy Kidzeum, a colorful museum where they can learn about keeping themselves and the planet healthy. Many of the exhibits are play-based – a perfect pick-me-up if they're getting fidgety after all that history.

With its vintage fighter planes, the Air Combat Museum might also appeal. Check ahead for opening times.

Alternatively, if you need to run off some energy, head to Knights Action Park, where you'll find arcade games, rides and mini-golf.

Springfield isn't just for families though – older visitors might like to follow the Capital City Bourbon Journey, which takes you on a tour of some fabulous bars and restaurants to try locally-produced makes.

Bonus: Springfield didn't invent the corn dog, but it does claim to be the birthplace of the iconic cozy dog – that's a hotdog on a stick covered in tasty batter for out-of-towners. For one of the best in town, head to the Cozy Dog Drive-In.

Our travel tips: Springfield will feel chilly if your spring break falls earlier in the season, with March temperatures rarely topping 50 degrees Fahrenheit. You might even see a little snow.

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Weekend trips (about 5 hours each way)

If you're able to spend a little longer on the road, then some more great destinations are within reach where you spend time relaxing in nature or enjoying the big city buzz of Columbus.

3. Cincinnati, Ohio

5 hours from Chicago (290 miles)

Why you should visit: Cincinnati is a beautiful riverside city which is at the longer end of the one-day range – it's also a great place for an overnight trip. There's plenty going on so it will appeal to visitors of all ages.

If your spring break coincides with Opening Day, come and join the party in Cincinnati. With unbeatable baseball heritage, the first pitch of the season sees the Findlay Market Parade and other events to celebrate the Reds (who always play their opening game at home).

Colorful Cincinnati river front looking from Kentucky with steam boat and ferris wheel.

How to get there: Follow the interstate as far as Indianapolis. You can stop for a break here but if you'd rather head straight to then bypass the city on I-465 which takes you onto I-74. Follow this road all the way to Cincinnati.

Our highlights: Baseball fans should head straight to the Cincinnati Reds Hall of Fame & Museum, where you can also take a tour of the Great American Ballpark.

If you're not in town for Opening Day, there's still plenty to see and do. Cincinnati Zoo holds its popular free Tunes & Blooms sessions on Thursday evenings through April. Enjoy live music among the colorful spring blooms in a family-friendly atmosphere. You can also enjoy the blooms in the daytime if you need to hit the road back to Chicago by the evening.

At Krohn Conservatory, the spring sees the arrival of thousands of butterflies which are fascinating to watch when you visit the tropical glasshouse.

With its Dinosaur Hall and interactive science exhibits, Cincinnati Museum Center is also a great family day out. Head to the Children's Museum for some play-based fun.

Bonus: For many years, the baseball season was officially opened with a first pitch in Cincinnati, whose team, the Reds, was the first in the country to go fully professional.

Our travel tips: The city will be really busy if you do visit for Opening Day, so expect some queues and leave extra time to park (we'd suggest arriving early). Book early if you want to try to get tickets for the game.

4. Traverse City, Michigan

5 hours from Chicago (320 miles)

Why you should visit: This is the only destination on our list that lets you carry on exploring the shores of Lake Michigan.

After the long winter, the wildflowers start to blossom around Sleeping Bear Dunes National Lakeshore, making this a fabulous weekend destination for fans of the great outdoors.

A weathered wooden walkway on the Empire Bluffs Trail is the perfect overlook to see Lake Michigan, the Sleeping Bear Dunes, and the Manitou island

How to get there: The interstate runs parallel to the shore of Lake Michigan most of the way to Traverse City. You'll start out on I-90 E before switching on to I-94. Follow this past Benton Harbor then change onto I-196 where the interstate divides. When you reach Grand Rapids join US-131 and continue north until you reach your destination.

Our highlights: You could spend days exploring the fabulous lakeshore, but seeing as you're only here for the weekend we'd suggest starting at Sleeping Bear Dunes with a hike along the Old Indian Trail or spending some time exploring Old Mission State Park. You can also visit the historic lighthouses – six in all – to enjoy more atmospheric views out across the lake.

It's too early in the year to swim in the lake but kids of all ages will love the huge indoor water park at Great Wolf Lodge.

If you're here without the family, visit a winery or two or taste some of the wine produced along the Traverse Wine Coast at one of the city's tasting rooms or bars.

Bonus: Traverse City is known as the Cherry Capital of the World. Spring break is out of both the cherry blossom and picking seasons, but don't miss the chance to try a slice of cherry pie while you're in town.

Our travel tips: Temperatures often dip below freezing even in April, and this can be a wet time of year, so plan for some indoor activities if you're making a spring trip here.

5. Columbus, Ohio

5 hours 30 mins from Chicago (350 miles)

Why you should visit: Ohio's state capital and largest city is packed full of things to do during spring break. The length of the drive means you'll probably want to stay at least a night (or maybe longer) but there's so much to do when you arrive that you definitely won't be bored.

You'll find a whole host of family-friendly attractions in Columbus, including one of the best science museums in the country at the Centre of Science and Industry.

The Ohio Statehouse in Columbus, Ohio

How to get there: Follow I-65 away from Chicago then at Indianapolis change onto I-70 to head east into Ohio. As you approach Columbus, merge onto I-670 to make your way to the downtown area.

Our highlights: The Center of Science and Industry (COSI) – named "America's number one science museum" – is packed full of interactive and informative exhibits which are guaranteed to keep children entertained for hours.

Another surefire hit with children is the LEGOLAND Discovery Center. It doesn't just appeal to kids, though. There's a 3D cinema featuring Lego characters, as well as the chance to build and explore interactive displays.

Just outside town, Columbus Zoo & Aquarium is another entertaining attraction, and if your spring break coincides with Easter there are extra egg-themed activities and attractions

If you're feeling active, head to Hocking Hill State Park, where you can escape the busyness of the city and hike through a fascinating sandstone landscape.

Staying outside, you can also visit Franklin Park Conservatory & Botanical Gardens, where the spring flowers will be starting to burst into life. It's a relaxing place to escape the hustle and bustle, and if you're traveling as a family children love exploring the tropical conservatory too.

Finally, to celebrate the spring sunshine, round off the afternoon or evening on one of the city's rooftop patios.

6. Cleveland, Ohio

Why you should visit: As well as spending time by another of the Great Lakes, this trip from Chicago to Cleveland also lets you follow one of “America's most scenic drives” with a detour along Indiana's Heritage Trail that starts at Elkhart.

If your spring break falls over the Easter period, come and join in the Dyngus Day celebrations! Held on Easter Monday, this Polish festival includes polka dancing, accordion music and beer tents – a really unique way to spend the spring break whatever your age!

Another interesting event that coincides with spring break is the Cleveland Thyagaraja Festival, a celebration of Indian classical music that brings international stars to the city.

Cleveland, Ohio, USA downtown city skyline and harbor at twilight.

How to get there: From the center of Chicago, join I-90 and keep going. You'll drive all the way across Indiana and then into Ohio, passing to the south of Toledo and Lake Erie before arriving in Cleveland.

If you're following the marked Heritage Trail, leave the interstate at Elkhart then head east on IN-120 to Bristol. Carry on to Middlebury and Shipshewana before looping back around to visit Goshen and Nappanee. Wakarusa is the final stop on the trail, which then passes through Elkhart again before you rejoin I-90 to continue east towards Cleveland.

Taking this detour along the Heritage Trail will add around 2 hours and 30 minutes to your driving time, plus any time for stops in the towns you'll pass along the way.

Our highlights: On your way to Cleveland, take a break from the interstate to travel along Elkhart County's Heritage Trail. Taking you through small towns and beautiful landscapes, you can download a free audio guide which gives you some of the background to this peaceful part of Indiana.

Once you've arrived in the city, you should definitely try out Maple Sugaring if you're visiting in March. This takes place at a number of locations in and around Cleveland.

If you're traveling with children, check out the themed trips on the Cuyahoga Valley Scenic Railroad, which run through April.

If the weather's good enough to spend more time outdoors, go for a longer hike through Cuyahoga Valley National Park where Brandywine Waterfall should be in full flow. You could also spend a peaceful half hour walking through the daffodils that carpet Lake View Cemetery.

Bonus: Cleveland Thyagaraja Indian classical music festival is the biggest festival of its kind that you'll find without visiting India.

Our travel tips: As with some of the other destinations listed so far, spring weather in Cleveland can be unpredictable, ranging from late snow to bright sunshine.

READ MORE - Road Trip from Chicago to Cleveland

Long weekend trips (6-8 hours each way)

There are some fantastic 3-4 road trips that you can take from Chicago. Visit another of the Great Lakes or head south to explore Tennessee's vibrant cities and stunning hills and mountains.

7. Nashville, Tennessee

7 hours 15 mins from Chicago (480 miles)

Why you should visit: Nashville is the first of our road trip destinations where you're likely to be able to enjoy some warmer spring weather, and the first one outside the Midwest.

Nashville is a great place to party , and with live music and warm weather likely to feature, it's perfect for a short spring break road trip from Chicago. It's a straightforward interstate drive south for the weekend, and once you arrive, you can immerse yourself in the party atmosphere until it's time to leave.

It's also a fun place to take children, especially if they're happy to soak in the atmosphere. Many of the live venues on Lower Broadway welcome families during the daytime.

Nashville, Tennessee, USA with colorful neon store signs hang along the bars restaurants and record stores along Broadway Street in downtown Nashville.

How to get there: Although it's a pretty long drive, this 475-mile route is really easy to navigate. Just hop onto I-65 as you exit Chicago to the south, and follow it all the way through Indiana and Kentucky. Just after you cross the Cumberland River, turn onto I-40 to make your way into Nashville's downtown where you'll complete your drive.

Our highlights: You can't visit Nashville without seeing a live show or two, so head to Music Row and take your pick before partying late into the night on Broadway. Some venues host special spring break parties, but if these don't match the kind of vibe you're after there are plenty of other venues to choose from.

A great all-year-round attraction that's a must-see in Nashville is the Country Music Hall of Fame. If really you want to immerse yourself in the heritage of Music City, you can carry on to the Johnny Cash Museum, RCA Studios or the Grand Ole Opry House.

When you're ready to take a break from wall-to-wall music, head to the Cheekwood Estate where the springtime Cheekwood in Bloom event sees over 100,000 tulip bulbs filling the peaceful gardens with bursts of color.

Just outside the city, Treetop Adventure Park is great for couples, groups and families alike – test your nerves as you travel across bridges, ropes and ziplines high up in the canopy (children must be over 7 to take part, and an adult has to climb with them).

Bonus: Book a stay at the Gaylord Grand Ole Opry Resort to enjoy a host of springtime activities for families.

Elvis recorded dozens of songs in Nashville, and with so many live acts performing in the city, you might one day be able to say you saw the next big music star before they were famous.

Our travel tips: This part of Tennessee is known for its spring tornadoes. It's unlikely that you'll see one but watch out for local advisories while you're in town.

Even this far south you'll need to pack warm clothes as the evenings will be cool and the weather can still sometimes be unsettled, especially in early spring.

READ MORE - Road Trip from Chicago to Nashville

8. Knoxville, Pigeon Forge and Gatlinburg

8 hours from Chicago (550 miles)

Why you should visit: With the mild Tennessee spring weather in your favor, you can leave your winter gear behind and enjoy time in the great outdoors on this trip.

The Great Smoky Mountains will be bursting with color in the spring, from the lush new leaves on the trees to the carpet of wildflowers.

In between the winter snow and sometimes humid summer heat, spring break is the perfect time to lace up your hiking boots and explore. If you need to keep teens or older kids entertained too, the fun attractions at Gatlinburg and Dollywood will be just the ticket.

Great Smoky Mountains, Tennessee, USA taken at sunset with the horizon over the Great Smoky Mountains from Morton overlook on the Newfound Gap Road in Gatlinburg, Tennessee.

How to get there: Follow the route toward Cincinnati along I-65 and I-74, then take I-275 to bypass the city itself. You'll cross the Ohio River to enter Kentucky, then follow the interstate south towards Lexington. Continue along I-75 and you'll reach Knoxville around an hour after crossing the state border into Tennessee.

To reach Pigeon Forge and Gatlinburg, take I-40 out of Knoxville then turn south on TN-66. From Sevierville, turn onto Parkway which takes you to both towns. This part of the trip will add just over an hour to your drive time.

Our highlights: While you're in Knoxville, enjoy the city's nightlife under the beautiful dogwood blossoms, and check out April's Chalk Walk which sees colorful art on sidewalks across downtown.

When you're ready to head out of town, make for Great Smoky Mountains National Park where trails and lookouts are abundant, or follow the Newfound Gap Road for a spectacularly scenic drive through the mountains.

Just outside nearby Pigeon Forge, Dolly Parton's Dollywood amusement park is a firm favorite with visitors of all ages.

Thrill seekers should definitely head to Gatlinburg's Mountain Coaster, which races rollercoaster-style down the side of the mountain, or Smoky Mountain Ziplines, where you can get a whole new view of this beautiful part of the world.

Bonus: Great Smoky Mountains National Park receives more visitors than any other national park in the United States – more than 11 million a year.

Our travel tips: Because of its popularity the roads into the national park can feel a little crowded at busy times, especially during spring break. Parking lots fill up and you might hit traffic delays. Visit early in the day or in the evening if you want to avoid the crowds – you're also more likely to see wildlife at these times.

READ MORE - Road Trip from Chicago to the Great Smoky Mountains National Park

Longer trips (Over 8 hours each way)

While a drive of this length probably won't suit spring breakers with young families, this is a great time to take an adventure with older children or to hit the road with a group of friends.

Whether you're heading south for the sunshine or taking in the views on a scenic drive through Minnesota, stop off to explore the towns and cities along the way to add to the fun.

9. Chattanooga, Tennessee

9 hours 20 mins from Chicago (610 miles)

Why you should visit: Built around the Tennessee River and overlooked by Lookout Mountain, Chattanooga is a city where you can easily combine active adventures with big-city entertainment.

For a longer spring break trip, stop in Nashville as well to enjoy even more of Tennessee's southern charm and hospitality.

Attractions in Chattanooga put on special events as part of the Spring Break Safari, making the city the perfect family spring break destination. There are child-focused art, science and nature activities on the itinerary, as well as the chance to explore caves, ride the Tennessee Valley Railroad or visit the Tennessee Aquarium.

Seven States Stone at Rock City viewpoint atop of iconic Lookout Mountain, Georgia. The city of Chattanooga Tennessee is nearby.

How to get there: Follow I-65 all the way to Nashville, where you'll merge onto I-24 after a brief stretch on I-40 as you cross the city. I-24 then takes you all the way to Chattanooga, crossing the Tennessee River Bridge then dipping into Alabama for about a mile before you complete your journey in the far south of Tennessee.

Our highlights: Tennessee Aquarium is one of the stops on the Spring Break Safari and the world's biggest freshwater aquarium. Check out the penguins, otters, and alligators, as well as plenty of underwater favorites.

The Creative Discovery Museum is a firm favorite with younger children. It features fun, interactive science-based exhibitions that will keep them entertained for hours.

Another must-see in Chattanooga is Ruby Falls, a waterfall and cave system which sits under Lookout Mountain. The mountain itself towers above the city and if you're feeling energetic you can hike right up to the top for amazing views across Chattanooga and into Georgia.

A great activity for families or groups of friends, you can take a small pedal-powered boat out to enjoy food and drinks on the Tennessee River.

Bonus: Miniature golf was invented in Chattanooga nearly a century ago, so why not play a round during your stay in the city?

Our travel tips: Chattanooga is notorious for its traffic so avoid traveling in the morning or evening rush hours if possible

10. Hot Springs, Arkansas

10 hours 40 mins from Chicago (700 miles)

Why you should visit: As well as being a great spring break destination, you can turn the drive to Hot Springs, AR, into a fabulous longer road trip with stops in Springfield and St Louis along the way.

People have been coming to Hot Springs in search of the healing powers of its naturally heated spring water for nearly 200 years, so if you're in need of some relaxation and downtime during spring break, this is the place to come.

Steaming waterfall with clear green water and trees on the banks

How to get there: Follow I-55 southeast through Illinois, passing Springfield before you cross the Mississippi River at St Louis, Missouri. After following the interstate south out of the city, turn onto US-67 which winds its way through the gently rolling hills of Missouri and into Arkansas.

At the town of Corning, turn right to continue along US-67/US-62, sticking with US-67 when the highways divide at Pocahontas. At Bald Knob the road merges with US-167 which takes you to the state capital Little Rock. Follow I-30 W out of the city, then turn onto US-70 for the final stretch of your drive to Hot Springs.

Our highlights: Top on most people's list in Hot Springs is a visit to a spa or geothermal spring. There are plenty to choose from, depending on whether your want a traditional bathing experience or a full day of pampering and relaxation.

Bathhouse Row is a National Historic Landmark District where 8 historic bathhouses still stand. Most no longer operate as bathhouses, but at Buckstaff Bathhouse you can still experience the same hot spring bathing experience that the first visitors here in 1912 would have enjoyed.

If some of your group are less interested in spa time than others, Adventureworks Hot Springs is a more active alternative. Ride zip lines and tackle a treetop rope course.

Crystal Ridge Distillery offers informative tastings and free tours where you can find out about the history of the moonshine that's traditionally been produced in this part of the country.

Bonus: The mineral-rich water from the hot springs is said to have healing qualities, and there are fountains across the city where you can take a drink or fill a bottle.

If you happen to be in Hot Springs over St Patrick's Day you can watch “the world's shortest St Patrick's Day Parade”. The event travels less than 100 feet but features several lively Irish-themed entertainment acts.

Our travel tips: Although there are a few natural open-air pools where the hot spring water travels down the mountain, bathing in them is not permitted. You can only soak in the geothermal water at Hot Springs at indoor bathhouses and spas.

11. Highway 61 Scenic Drive

11 hours from Chicago (710 miles)

Why you should visit: This trip takes you right up to Grand Portage on the Canadian border, which is the northernmost point on our list.

Spring is one of the best times of year to see the Northern Lights, which are visible along this route. It's an unforgettable spectacle which is definitely worth the long drive out from Chicago. With the weather still feeling wintery, book into a cozy cabin and enjoy quality time together over spring break.

A Band of Green Northern Lights behind Partly Cloudy Night Skies above Traffic Trails on Highway 61 in Northern Minnesota

How to get there: Follow I-90 W out of Chicago for around 100 miles until you reach Wisconsin, then continue for another 100 miles to merge with I-94. From here the road takes you through Eau Claire before arriving in the twin cities of St Paul and Minneapolis.

Exit the city via I-35 W for a couple of miles, before continuing on I-35 N in the direction of Duluth. The interstate ends here and you'll complete your road trip by following Highway 61 Scenic Drive, which follows the shore of Lake Superior all the way to Grand Portage at the Canadian border.

Our highlights: If there is still snow on the ground, that means you can take a scenic dog sledding trip to explore the wild landscapes of the scenic north shore.

The scenic drive along the North Shore is one of the main attractions of this road trip, so make sure you leave plenty of time to stop and enjoy the views along the way.

If the snow has melted, pack your hiking boots and set out to explore Tettegouche, Temperance River or Cascade River State Parks, which are all easily accessed from Scenic Route 61 along the lakeshore.

At Lutsen you can ski in colder months or, if spring has come early when you visit, head up to the peak via gondola to enjoy stunning views.

Bonus: You can't drive this route without stopping off in Grand Marais to visit World's Best Donuts, a local legend.

Our travel tips: As you might expect this far north, temperatures can be cold especially if your spring break falls early in March. Heavy snow is possible but not guaranteed during March and April, so stay flexible in your choice of activities if you take this trip.

This trip is probably best suited for travelers who can visit a little later in the season if they want to comfortably spend more time outdoors.

12. Atlanta, Georgia

11 hours from Chicago (730 miles)

Why you should visit: Atlanta is the southernmost destination on our list and is an amazing place to visit from Chicago during spring break .

You're almost certain to enjoy some much-needed spring sunshine here, without the large crowds that you'll find further south in Florida or on the coast.

Centennial Olympic Park in Atlanta during twilight hour after sunset

How to get there: Head south through Nashville to Chattanooga on I-65 and I-24. As you enter Georgia just south of Chattanooga, I-24 merges with I-75 which takes you as far as the suburbs of Atlanta.

Depending on your final destination in Atlanta, you'll probably join up with I-85 to complete your journey in the city's downtown.

Our highlights: Families should head straight to Centennial Park, a huge outdoor space which covers the site of the 1996 Olympic Park. The Children's Museum of Atlanta is on the edge of the park too.

Zoo Atlanta is a must-see for visitors of all ages. It's one of the only places in the United States where you can see Giant Pandas, alongside many other endangered species.

There's also a wealth of sites dedicated to modern US history and the Civil Rights movement in Atlanta, including the National Center for Civil and Human Rights and Martin Luther King Junior National Historical Park.

If you're traveling with older spring breakers, Six Flags Over Georgia theme park is a great stop, and sports fans should definitely check out the College Football Hall of Fame.

Bonus: Coca-Cola originated in Atlanta in the 1880s, which is why you'll find the World of Coca-Cola in the city today.

Our travel tips: “Rush hour” in Atlanta lasts all day. Allow plenty of time for your journey if you're using your car to get around the city.

READ MORE - Road Trip from Chicago to Atlanta

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'Not our best night': Tigers start 10-game trip with 5-0 loss against Angels

best road trips starting in chicago

Anaheim, Calif. — This is going to be a long, long trip for the Tigers. Ten games, three cities, across three time zones. Excruciatingly long if the bleary loss Thursday night was any kind of precursor.

"It is frustrating," manager AJ Hinch said after the Tigers were blanked 5-0 by the Angels in the first of four games at Angels Stadium. "It's an opportunity missed to do better. We said this was an important road trip and it's not off to a great start. We have to bounce back tomorrow but certainly disappointed with the day."

The offense was disarticulated by rookie right-hander Davis Daniel. He’d debuted out of the bullpen last season but this was his first big-league start. And the Tigers, with just four hits in eight innings against him, had no answers.

"Not our best night," said Matt Vierling. "He was filling up the strike zone and getting ahead of us. Just throwing a ton of strikes."

He had a lot of Tigers shaking their heads on their way back to the dugout. He was far from overpowering. Off a 91.7-mph four-seamer, he mixed changeups, sliders and a few curveballs. But the Tigers couldn't square much up against him.

"I thought I had a couple of at-bats, too, where I got pitches in the zone and couldn't capitalize on them," Vierling said. "He was filling up the zone and we weren't taking advantage of pitches in the zone that were hittable."

BOX SCORES: Angels 5, Tigers 0


The Tigers came out in attack mode. Vierling bounced the first pitch of the game for a single. And they kept attacking early, but weren't doing any damage. The aggressive approach turned passive later. They ended up taking 17 called strikes on Daniel’s fastball.  

"He beat us inside the strike zone with a lot of strikes and a lot of count leverage and a lot of swings that weren't on time," Hinch said. "He continued to be relentless in the zone with strikes because it was working for him."

Riley Greene had two of the team's four hits. He doubled with two outs in the first inning and that was the last time they put a runner in scoring position until the eighth when Wenceel Perez singled and advanced on a ground out. And went no farther.

More: With pitching depth thinning, Tigers may consider sliding Brieske into rotation

Two at-bats with runners in scoring position is not the sign of a healthy offense. Nor was the eight strikeouts and the mild 85.6 mph exit velocity on 18 balls put in play.

Tigers' starter Jack Flaherty attacked the strike zone early, too. But the results were much different.

"They put some good swings on some good pitches and they put some good swings on some balls that I didn't have very good command of," Flaherty said. "I put some guys away when I needed to and got in a good little stretch there. But overall, not really good command of pretty much everything."

Flaherty hadn’t allowed more than three runs in any of his previous nine starts. But he gave up three home runs in the first five innings to an Angels lineup that remains without Mike Trout and Anthony Rendon.

Miguel Sano got a center-cut, 95-mph four-seamer leading off the second inning and swatted it 406 feet into the rocks in center field.

Flaherty got beat with another fat fastball with two outs in the fourth. Willie Calhoun sent a first-pitch heater into the seats in right field.

"You go out and attack and you throw first-pitch strikes, you are going to give up first-pitch homers," Flaherty said. "That's what happened. Willie put a good swing on it. But you want to keep attacking."

After Flaherty gave up a two-out RBI single to rookie Nolan Schanuel in the fifth, Luis Rengifo launched a 3-2 slider into the seats in right, a two-run homer.

Five of six hitters in the fourth and fifth innings attacked first pitches from Flaherty.

"You could see it, they changed their approach and super aggressive on first pitches," Flaherty said. "If you execute those pitches, good things happen. If you don't, things aren't great."

He got the first two outs in the sixth inning, but he was laboring. He gave up a two-out single to catcher Logan O’Hoppe and then threw two wild pitches, both sliders in the dirt.

Right-hander Beau Brieske was summoned to get the final out.

"Bad start, that's about it," Flaherty said.

The loss drops the Tigers to a season-worst seven games under .500 (37-44). But, on the flip side, that 37-44 record is the club's best at the 81-game midpoint in eight seasons.

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