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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

“Such an amazing experience! A must see while in Chicago! Tour guide was funny & knowledgeable, I did not realize there was so much history regarding the architecture of Chicago at all! I left the tour feeling so proud to be there exploring the city, that experience really fueled my fire to learn more!”

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

“If is cold dress accordingly Other then that I will definitely go again when it is sunny and hot outside”

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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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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4.Chicago: Gangsters and Ghosts Walking Tour

A historian-led Chicago Loop walk mixing Prohibition-era mob stories and reported ghost sites, with optional minibus upgrade for $52.

★ 5.0

“We had been walking the same area but knowing the history definitely made our trip more interesting. Sophia was great! Congrats on getting engaged Sophia!”

7,155 reviewsFrom $52by Chicago Tours

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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

“The deck where photos are taken, staff can be more consistent with the time limit for each party taking a photo. They have signs posted for two or three minutes for each group. Some staff allowed more time for some groups and rushed other groups off. Not a consistent practice and it is noticeable which…”

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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7.Chicago: Architecture River Cruise Skip-the-Ticket Line

Skip the ticket line for Chicago’s architecture river cruise with a live docent, 40 landmarks, and a cash bar on 3 river branches.

★ 4.8

“It was awesome! Tons of history and architecture! Our guide Victor was amazing and non stop full of information, a little humor and just a ton of knowledge. I could listen to him for hours!”

4,325 reviews1 hourFrom $39by Shoreline Sightseeing

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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

“We had so much fun and learned a lot! Our tour guide Mike was informative and hilarious! Would do this again!”

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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9.Chicago River 45-Minute Architecture Tour from Magnificent Mile

Take a 45-minute Chicago River architecture cruise from the Magnificent Mile with live narration, top-deck views, and major landmarks.

★ 4.5

“Very informative about the architecture of Chicago. Tes, the narrator was fabulous. You could hear every word. Very articulate. She made interesting in 40* weather. 45 minutes was perfect in the cold.”

2,924 reviews45 minutes (approx.)From $28.00by Wendella Tours & Cruises

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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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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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12.Chicago: 45-Minute Family-Friendly Architecture River Cruise

A 45-minute Chicago River family architecture cruise with live English guide, indoor and outdoor decks, and skip-the-line entry for $28.

★ 4.7

“Perfect ending to a looo...ng day walking the Windy City. Learned some fun facts, and really thought 45min were quite alright. Doing this tour during sunset was breathtaking - so many colours! Definitely a nice thing to add to your to-do list.”

2,304 reviews45 minFrom $28by Wendella Tours & Cruises

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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

“Bus drivers were friendly, on time and helpful - knew the best local restaurants and Chicago specialties. The bus also takes you to the 'must-see' sights and attractions of Chicago, even during a winter trip! It felt safe for a female solo traveller and would be fun in groups as well - highly recommend.”

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

“This tour was great! We got to try all the most famous Chicago foods while learning all about the city. Jessika was an excellent guide. She told captivating stories and kept us entertained throughout! We had a great time!”

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

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