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Chicago Tours & Trips
Find the right tour for you through Chicago. We've got 56 adventures going to Chicago, starting from just 7 days in length, and the longest tour is 38 days. The most popular month to go is September, which has the largest number of tour departures.
56 Chicago tour packages with 34 reviews
- Coach / Bus
Mackinac Island & the Great Lakes
Chicago, Niagara and New York
- Sightseeing
Toronto, Niagara and Chicago
Rhythms of the Road (including Hammond)
tour took us exactly where we wanted to go with someone else doing the organising!
- In-depth Cultural
Highlights of Route 66
The tour guide, John, made the trip fun, entertaining, and he was so knowledgeable of the route
Chicago to LA
It was a breathtaking tour. I loved that we stopped at so many national parks and in the evening had alone time to process the day. The guide was amazing.
- €150 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.
Chicago Blues
- Christmas & New Year
North East Highlights (7 Days)
- €100 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.
Mackinac Island (Chicago, IL to Southfield, MI)
Chicago to Golden Gate
New York to Hollywood
- Active Adventure
Heartland Harmony
Music City to Windy City
- Festival & Events
Mackinac Island featuring the Grand Hotel and the Tulip Time Festival (Chicago, IL to Southfield, MI)
- Train & Rail
Trans-American Rail Journey (2024)
Reviews of chicago tours.
Clinton Dunn and Kathy in Petosky were exceptional tour guides and we had a teriffic time.
Would’ve loved it to have been longer! An extra night in each main city would’ve been great for extra activities
Very informative with Tour Director’s wealth of information about the whole Tour. Well done John!!
Tours starting from Chicago
- for 10 Days (8)
- to North America (14)
- to USA (14)
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International Versions
- Deutsch: Chicago Rundreisen
- Français: Circuits et voyages au Chicago 2024/2025
- Español: Circuitos y viajes por Chicago 2024/2025
- Nederlands: Chicago Rondreizen 2024/2025
Chicago Tours
Chicago is a sprawling city, comprised of dozens of neighborhoods with unique characteristics and singular attractions. It can be hard to approach exploring the city without an insider’s knowledge of the best way to get to Wicker Park, or the top pizza place in River North. Fortunately, there’s a wide variety of tours available in Chicago to help visitors make the most of their time in the city while easily navigating the best attractions, areas, and cuisines.
For first-time visitors, bus tours are a smart option. They can help you see more of the city than you would be able to via mass transit (without some very complex planning, that is). Bus tours also allow you to see the highlights of the city via a pre-planned route that maximizes sightseeing potential and minimizes driving time. Hop-on hop-off options are key here, too, as they facilitate exploring the city at your own pace, and visiting attractions that pique your interest from the bus. There are even themed bus tours that cover topics like food, drink, and Chicago culture.
Chicago boasts many types of tours beyond the typical bus tour, however. If you’d like to experience Lake Michigan or the Chicago River – two essential components to the city’s identity – then a boat tour is a smart option. You can choose a tour that simply showcases the lake, or one that highlights city architecture. Visitors can also opt to explore the via bike: take a guided tour or explore on your own. Given that Chicago is a very walkable city, it’s unsurprising that another popular type of tour is a walking tour. These are usually themed around a concept like food, drink, pop culture, local legends, and more. The Chicago Architecture Center also runs many architecture-specific tours, and many companies offer guided tours (on foot or via bus) related to culinary concepts.
Whatever kind of tour you’re interested in, you’ll find a number of excellent options in Chicago. Here’s an overview of the most popular tour types in Chicago.
The classic option for exploring Chicago, bus tours come in a variety of styles ranging from guided tours of the North and South Sides to fully-narrated hop-on hop-off tours.
With Lake Michigan and the Chicago River being so important to the city, it’s no surprise that you can tour the city via boat. Choose a theme, or just enjoy the sail.
Explore the city in an eco-friendly way by making your way through the parks and trails of Chicago on two wheels. Take a self-guided tour, or opt for the full experience.
Walking Tours
In spite of its massive size, Chicago is the ideal city for a walking tour. Explore a neighborhood, a theme, a concept, or a story on these guided excursions.
If you’re interested in Chicago’s culinary scene, then a food tour is a must. They’re organized around neighborhoods or cuisines and are perfect for foodies.
Architecture Tours
Chicago’s architectural legacy is among the best in the country. Enjoy the amazing, inspiring buildings that populate the city skyline on an architecture tour.
Tour Companies
Gray line chicago.
Gray Line Tours offers 5 different tour options in Chicago. Popular Gray Line Chicago tours include the Chicago Grand City tour, the Chicago North Side tour, and the Historic Chicago South Shore tour.
Chicago Crime Tours
Takes visitors on guided outings to a number of famous crime scenes. Along the way, guests will learn about Chicago’s history as a hotbed for criminals like John Dillinger, Al Capone, and more.
Bike and Roll Chicago
Offers a variety of guided bike and Segway tours that take visitors to a number of Chicago’s most iconic attractions. They also offer bike rentals by the hour or day.
Tall Ship Windy
Based out of Navy Pier, Tall Ship Windy operates a variety of scenic cruises on its approximately 150-foot schooner. Popular tours include the Lakeside Architecture Sail and the Skyline Sail, with several other options available.
Big Bus Chicago
With their distinctive fleet of open-top, double-decker buses, Big Bus Chicago offers hop-on, hop-off tours that let you choose where and when you stop at a given attraction.
Shoreline Sightseeing
Has been running scenic tours of Chicago along Lake Michigan and the Chicago River for 80 years. Their most popular tours include a river excursion highlighting Chicago’s acclaimed architecture and a lake cruise departing from Navy Pier .
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10 Best Chicago Tours & Trips 2024/2025 - TourRadar. Home. / North America tours. / USA tours. / Chicago tours. Chicago Tours & Trips. Find the right tour for you through Chicago. We've got 56 adventures going to Chicago, starting from just 7 days in length, and the longest tour is 38 days.
The best Tours, Sightseeing & Cruises in Chicago according to Viator travelers are: 90-Minute Chicago River Architecture Tour; 45-Minute Chicago River Architecture Tour from Magnificent Mile; Chicago Architecture River Cruise; Gangsters and Ghosts Tour in Chicago; 360 CHICAGO Observation Deck Admission (Hancock Center)
Take a Chicago tour with a friendly local guide and discover the best the Windy City has to offer. Take a riverboat cruise for a fresh perspective on Chicago's striking architecture. Your guide will point out the world's first skyscraper, whose steel frame revolutionized the building of office towers.
The best tours to do in Chicago with kids are: Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket; Chicago: Navy Pier Centennial Wheel Regular & Express Ticket; Chicago: 45-Minute Family-Friendly Architecture River Cruise; Chicago: Willis Tower Skydeck and The Ledge Ticket; Chicago: Gangsters and Ghosts Guided Walking Tour
Choose a theme, or just enjoy the sail. Bike Tours. Explore the city in an eco-friendly way by making your way through the parks and trails of Chicago on two wheels. Take a self-guided tour, or opt for the full experience. Walking Tours. In spite of its massive size, Chicago is the ideal city for a walking tour.