Category Chicago Tours

Chicago · CHICAGO TOURS

Chicago Tours: The 15 Best in the City

408 tours

Boats, buses, bikes and two feet: Chicago gives you every shape of tour and no obvious way to choose between them. The 15 below are the strongest running right now, with prices, running times and the reason each one earns its place.

Chicago Architecture River Cruise

Chicago Architecture River Cruise - The Skyline Roll Call: Wrigley, Hancock, Willis, and Iconic River Views

1.Chicago Architecture River Cruise

★★★★★★★★★★5.0 · 15,756 reviews · 1 hour to 1 hour 30 minutes (approx.) · from $39Our pick

A pet-friendly Chicago River architecture cruise with live guide commentary, landmark views, and great value for $39, lasting about 1-1.5 hours.

“Such a great time!! Sam was our guide, and he was phenomenal. He told us the history of not only the buildings, but the city as a whole, and its relation to the nature it resides besides. Sam gave us historical and cultural context behind many architectural styles. He also had some great jokes. The cow puns… udderly hilarious. My friend and I are from Omaha (also called River City by locals), and we wish that our hometown had a river architectural tour like this.”

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Chicago River 90-Minute Architecture Tour

Chicago River 90-Minute Architecture Tour - Boat setup: upper deck for views, lower deck for comfort

2.Chicago River 90-Minute Architecture Tour

★★★★★★★★★★4.5 · 9,629 reviews · 1 hour 30 minutes (approx.) · from $45

Wendella’s 90-minute Chicago River architecture cruise with indoor warmth, big skyline views, and stories from 130+ years.

“The tour and tourguide were great! The time flew by and it was very interesting. If you have someone who needs the elevator to get to the dock, be sure to call the company for detailed instructions on how to get there. The staff was very helpful.”

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Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise - Getting to the dock near 400 N Michigan Avenue and choosing your deck

3.Chicago River: 1.5-Hour Guided Architecture Cruise

★★★★★★★★★★4.8 · 8,046 reviews · 1h 30m · from $44

A 90-minute Chicago River architecture cruise with expert guides, indoor climate comfort, and iconic skyline views for about $44.

“We really appreciate the service—our tour was both enjoyable and meaningful. We loved getting a historical view of the city and listening to such a professional and friendly guide. We actually wanted to leave a tip but didn’t have any cash with us. Having a barcode or QR code option for tipping would be really helpful. We also noticed how friendly the people around us were—they waved and interacted with us, which made the experience even better. Overall, it really changed the way I thought about Chicago.”

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Chicago: Gangsters and Ghosts Walking Tour

Chicago: Gangsters and Ghosts Walking Tour - The First Big Chunk: The Loop Walk With Restrooms and Refreshment Breaks

4.Gangsters and Ghosts Walking Tour

★★★★★★★★★★5.0 · 7,155 reviews · from $52

Chicago Loop gangster tales and ghost stories on a 2-hour historian walk. Millennium Park, Palmer House, Riverwalk, and Capone legends.

“Very exotic experience, another good way to know about Chicago history beside just regular tourist spots”

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Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady - The 90-Minute Value: Why This Cruise Works So Well for First-Time Chicago

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket - Getting there at S. Wacker Blvd, and how the line works

Chicago: Architecture River Cruise Skip-the-Ticket Line

Chicago: Architecture River Cruise Skip-the-Ticket Line - Your route: all three branches and 40 landmark buildings explained

7.Architecture River Cruise Skip-the-Ticket Line

★★★★★★★★★★4.8 · 4,325 reviews · 1 hour - 90 minutes · from $39

Skip the ticket line for a 3-branch Chicago River architecture cruise with live docent narration, skyline views, and optional drinks onboard.

“I recently had the pleasure of joining a boat tour led by our fantastic guide, Dillon, and Captain Albert, and I can't recommend them highly enough! From the moment we set sail, it was clear that we were in for an unforgettable experience. Dillon's enthusiasm and extensive knowledge made the tour both informative and engaging. He shared fascinating stories and insights about the local history and landmarks, making every moment on the water feel special. His passion for the area was contagious, and he encouraged questions, ensuring everyone felt involved. Captain Albert was the perfect complement to Dillon's guiding. His skillful navigation and calm demeanor made us feel safe and…”

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Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour - Meeting at 163 E Pearson, and the simple rule that keeps it smooth

8.Chicago Crime and Mob Bus Tour

★★★★★★★★★★4.5 · 3,186 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $49

Ride Chicago by coach on a crime-and-mob tour with comedy-bent storytelling, photo stops, and a mini mob museum for $49.

“Our host Dane was energetic and entertaining! We learned a lot on the tour and enjoyed the stops. Would recommend to those wanting to know more about Chicago history!”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

Chicago River 45-Minute Architecture Tour from Magnificent Mile - Choosing your deck: open-air views vs sheltered comfort

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour - Getting Comfortable: Seats, Restrooms, and the Wind on Lake Michigan

11.Chicago Lake and River Architecture Tour

★★★★★★★★★★4.5 · 2,308 reviews · 1 hour 30 minutes (approx.) · from $45

A 90-minute Lake Michigan and Chicago River boat tour with live architecture narration and skyline views from Wendella dock.

“Very informative. Bring a small blanket- it was chilly. But if you’re hot, you could sit on the blanket. The chairs were pretty uncomfortable.”

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Chicago: 45-Minute Family-Friendly Architecture River Cruise

Chicago: 45-Minute Family-Friendly Architecture River Cruise - The Route: Lakeshore Drive to Willis Tower, Then Back Past the Riverwalk

12.45-Minute Family-Friendly Architecture River Cruise

★★★★★★★★★★4.7 · 2,304 reviews · 45 min · from $28

A 45-minute Chicago River cruise with live architecture narration, indoor and outdoor decks, and a cash bar, perfect for families.

“Sarah was a great guide with a lot of interesting facts about the Chicago architecture. The 45 minute tour was just enough time to get a feel for the history of the city. The boat was comfortable and there were lots of seats for the guests. Highly recommend this tour.”

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - The Ride Experience: Double-Decker Views, Wi-Fi, and Audio Quality

Chicago: 1.5-Hour Lake and River Architecture Cruise

Chicago: 1.5-Hour Lake and River Architecture Cruise - Boarding near Michigan Avenue, plus the real-seat decision

14.1.5-Hour Lake and River Architecture Cruise

★★★★★★★★★★4.7 · 2,050 reviews · 1h 30m · from $44

Chicago’s architecture cruise mixes river views and Lake Michigan skyline time, includes expert narration, and features an onboard cash bar. From $44.

“We had the BEST guide of all time! A lovely tour with so much to learn - would absolutely tell a friend to try this when they visit Chicago.”

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Chicago Favorites Ultimate Food and Walking Tour

Chicago Favorites Ultimate Food and Walking Tour - Price and value: $84.99 for a real Chicago meal plus extras

15.Chicago Favorites Ultimate Food and Walking Tour

★★★★★★★★★★5.0 · 1,962 reviews · 3 hours (approx.) · from $84

A 3-hour food and walking loop through Chicago classics, Millennium Park sights, and downtown landmarks, plus a free bike or kayak bonus.

“We were combined with the Holiday food tour to make a group of 14 (Christmas Eve). Our guide, Fran, was personable and knowledgeable, and kept the group moving. My husband and I enjoyed the food and the stories--it was a great introduction to the city of Chicago.”

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