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15 Things To Do In Chicago

The best of Chicago.

The 15 most popular things to do in Chicago. Architecture river cruises, the Willis Tower Skydeck, gangster and speakeasy walks, lakefront cruises and the city’s best food tours, all in one place.

15 Things To Do In Chicago

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

“Very interesting and the architecture was beautiful . Alyssa the tour guide was very knowledgeable and had a good sense of humor .”

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

“John was an absolutely fantastic guide. Incredibly informative and so much fun. We traveled from Ireland and he was one of the highlights of á fantastic weekend in á city thst he is clearly and rightly proud of. Well done done John”

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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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

“Willis was a great story teller! Easy to find, the only wish is that we were able to stop in more places. Most of the tour is just walking outside not in actual buildings.”

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

“Had an amazing time on this in depth tour! Guide was upbeat and so knowledgeable, and kept the tour lively the whole time. Nice variety of architecture and local history. Loved the context part showing how each building is in conversation with those around it. Highly recommend!”

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

“We enjoyed our whole visit. Interesting Chicago Experience Museum including a Chicago train. Great views from the Sky deck. Going on the The Ledge was amazing. Only a short queue and although only have 90 seconds you can rejoin the queue and go in as many times as you like. We had plenty of time…”

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

“the tour is about mafia and talk more about jhon dillinger a bank robber and mc Donald selling crak then AL CAPONE the tour don't talk about capone the real gangster i specs to see the places he live or operate this tour is not good and expensive .”

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

“It was a well-organized tour where I had the opportunity to learn, observe, and fully enjoy the experience. Everything was explained clearly, the schedule was well managed, and the overall atmosphere was pleasant and professional.”

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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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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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

“The food walking tour was awesome! Our tour guide, Gabe, was fantastic! He was very informative and a great person to show us around a small part of the city. I wasn't sure if this tour would include enough food, but I was so wrong! At the end of the tour, my wife and I…”

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

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More Things To Do In Chicago

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Explore Chicago

From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.

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