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15 Best Chicago Tours & Experiences

The best of Chicago.

The 15 standout tours and experiences in Chicago. The days visitors still talk about long after the trip home.

15 Best Chicago Tours & Experiences

If you would rather see Chicago with a guide, HappyToVisit tallies the best-reviewed Chicago tours, and the official Choose Chicago and Enjoy Illinois sites cover hours and access.

Chicago Architecture River Cruise - Price That Buys Time (and a Real Narrator)
Chicago, Chicago River Architecture Cruises, Cruises & Boat Tours, Tour Reviews

Chicago Architecture River Cruise

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1.Chicago Architecture River Cruise

Chicago Architecture River Cruise with live expert commentary, skyline views, mobile tickets, pet-friendly boats, and about 1 hour on the water.

Most Popular★ 5.0

“Very informative. Ashley was a great guide. They tend to push buying your pictures, buying their drinks and snacks. Wish they had seat warmers for you.”

15,756 reviews1 hour to 1 hour 30 minutes (approx.)From $39.00by Shoreline Sightseeing

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Chicago River 90-Minute Architecture Tour - Indoor vs Outdoor: How to Get the Views You Want
Chicago, Chicago River Architecture Cruises, Tour Reviews, Tours

Chicago River 90-Minute Architecture Tour

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2.Chicago River 90-Minute Architecture Tour

A 90-minute Chicago River cruise with architecture narration, indoor climate control, and major-sight views of Wrigley Building, Marina City, and more.

★ 4.5

“Absolutely fabulous! I think our tour guide was Jack. He was just fabulous! Knowledgeable, funny, answered questions.”

9,629 reviews1 hour 30 minutes (approx.)From $45.00by Wendella Tours & Cruises

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Chicago River: 1.5-Hour Guided Architecture Cruise - Why 90 Minutes Feels Like the Right Amount of Time
Chicago, Chicago River Architecture Cruises, Cruises & Boat Tours, Guided, Tour Reviews

Chicago River: 1.5-Hour Guided Architecture Cruise

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3.Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River 1.5-hour architecture cruise covers main stem plus north and south branches. Expert guides, indoor comfort, deck views.

★ 4.8

“It was the most interesting architecture tour I have ever been!! The tour guide was very charismatic and made us laugh at lot, we explained everything in a very passionate way and we had a blast!”

8,046 reviews1.5 hoursFrom $44by Wendella Tours & Cruises

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Chicago: Gangsters and Ghosts Walking Tour - Meeting point and timing: how to start smoothly
Chicago, Gangster & Crime Tours, Ghost & Haunted Tours, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Ghosts Walking Tour

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Chicago Architecture Center River Cruise aboard First Lady - Price: What $57 Buys You (and Where the Value Really Comes From)
Chicago, Chicago River Architecture Cruises, Cruises & Boat Tours, Tour Reviews

Chicago Architecture Center River Cruise aboard First Lady

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5.Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center cruise aboard First Lady. 90 minutes of docent-led river views of Willis, Marina City, Navy Pier, and more.

★ 5.0

“Russel was an exceptional tour guide. Very knowledgeable. I love that we did this tour day 1 so that traveling throughout the city the rest of the trip I was able to connect points of interest to the tour and knowledge.”

5,536 reviews1 hour 30 minutes (approx.)From $57.00by Chicago Architecture Foundation & Chicago's First Lady Cruises

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Chicago: Willis Tower Skydeck and The Ledge Ticket - Entering Willis Tower Skydeck: lobby flow and security basics
Chicago, Skydeck & Observation Decks, Tickets, Tour Reviews

Chicago: Willis Tower Skydeck and The Ledge Ticket

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6.Chicago: Willis Tower Skydeck and The Ledge Ticket

Willis Tower Skydeck with The Ledge glass balcony in Chicago. Timed entry, museum exhibits, and a thrilling skyline view for about 45 minutes.

★ 4.6

“Willis Tower and The Ledge offer an unforgettable experience with stunning panoramic views of Chicago. Stepping onto the glass floor of The Ledge is both thrilling and surreal. A must-visit for anyone looking to see Chicago from a breathtaking perspective!”

4,350 reviews45 minFrom $42by Skydeck Chicago

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Chicago: Architecture River Cruise Skip-the-Ticket Line - The 3-Branch Route: Buildings You’ll Actually See
Chicago, Chicago River Architecture Cruises, Cruises & Boat Tours, Tickets, Tour Reviews

Chicago: Architecture River Cruise Skip-the-Ticket Line

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Chicago Crime and Mob Bus Tour - Meeting at Pearson Street and Finishing by Water Tower Place
Chicago, Gangster & Crime Tours, Tour Reviews, Tours

Chicago Crime and Mob Bus Tour

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8.Chicago Crime and Mob Bus Tour

A $49 coach tour through Chicago’s mob history with photo stops, mini museum, and story-first guides. 90–120 minutes of crime scenes.

★ 4.5

“Great narration about mobsters. Only stop to get out of bus to see where John Dillinger was killed and Frank Nitti’s vault.”

3,186 reviews1 hour 30 minutes to 2 hours (approx.)From $49.00by Chicago Crime Tours and Experiences LLC

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - Where you meet the boat at the Wrigley Building
Chicago, Chicago River Architecture Cruises, Sightseeing & City Tours, Tour Reviews, Tours

Chicago River 45-Minute Architecture Tour from Magnificent Mile

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Chicago: 360 Chicago Observation Deck General Admission - Getting In Smoothly: Skip the Ticket Desk, Expect Security Lines
Chicago, Observation Decks, Skydeck & Observation Decks, Tour Reviews

Chicago: 360 Chicago Observation Deck General Admission

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10.Chicago: 360 Chicago Observation Deck General Admission

Skip the ticket desk for fast access to 360 Chicago’s 94th-floor views, Lake Michigan panoramas, and optional TILT upgrade.

★ 4.4

“Wow! Wow! Wow! The views from the observation deck were out of this world- almost literally. I went at sunset and got some amazing photos. Great family activity, even though I went by myself. I bought tickets at the top for The Tilt and the extra $10 was worth it. Security was quick and the…”

2,534 reviewsFrom $30by 360 Chicago Observation Deck

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Chicago Lake and River Architecture Tour - Stop 1: Chicago River—history, water engineering, and classic skyline angles
Chicago, Chicago River Architecture Cruises, Lake Michigan Cruises, Tour Reviews, Tours

Chicago Lake and River Architecture Tour

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11.Chicago Lake and River Architecture Tour

One-and-a-half-hour Chicago architecture boat tour with live narration, River and Lake Michigan views, skyline photos, and climate-controlled seating.

★ 4.5

“Visiting Chicago from Ireland for first time with friends and this was an excellent way to kick off the holiday. Gives you good view of Chicago, learn a bit of history from your guide, indoors available if it’s cold. Overall perfect and price was perfect too very happy with it. Drinks were available on board…”

2,308 reviews1 hour 30 minutes (approx.)From $45.00by Wendella Tours & Cruises

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Chicago: 45-Minute Family-Friendly Architecture River Cruise - From Lakeshore Drive to Willis Tower: The Route You’ll Float Through
Chicago, Chicago River Architecture Cruises, Cruises & Boat Tours, Tour Reviews

Chicago: 45-Minute Family-Friendly Architecture River Cruise

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - Stop-by-stop: what to expect, why each stop matters
Chicago, Hop-On Hop-Off & Bus Tours, Sightseeing & City Tours, Tour Reviews, Tours

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

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

Hop-on, hop-off Big Bus Chicago gives you open-top views, audio commentary, and easy stops at top sights with 24/48/72-hour flexibility.

★ 4.0

“There was no working heat on our second bus upstairs. We froze waiting for the bus to arrive since they were only running each hour and times were way off. No one would communicate back with me on when they would arrive or how far away anyone was for our pick up location. They sign…”

2,191 reviews2 hours (approx.)From $45.00by Big Bus Tours - USA

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Chicago: 1.5-Hour Lake and River Architecture Cruise - Boarding at 400 N Michigan Avenue: what to know before you line up
Chicago, Chicago River Architecture Cruises, Cruises & Boat Tours, Lake Michigan Cruises, Tour Reviews

Chicago: 1.5-Hour Lake and River Architecture Cruise

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Chicago Favorites Ultimate Food and Walking Tour - Route and pacing: 1.25–1.5 miles, Pedway in winter
Chicago, Food, Food & Culinary Tours, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago Favorites Ultimate Food and Walking Tour

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15.Chicago Favorites Ultimate Food and Walking Tour

Taste Chicago classics on a 3-hour walking tour with deep-dish, Italian beef, hot dogs, brownie and popcorn plus a free 2-hour bike or kayak.

★ 5.0

“AJ did an amazing job not only bringing us to some amazing food but also telling us about the history of the city as we went, we learned so much we otherwise may have never learned!”

1,962 reviews3 hours (approx.)From $84.99by Bobby's Bike, Hike & Food Tours - Chicago

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