Chicago · TOUR REVIEWS

Chicago’s 15 Best Tours, From the River to the Rooftops

452 tours  ·  from $5 a head

A long weekend or a week in the city, the problem is the same: one river, one lake, too many towers to climb. These 15 are the days that earn their slot, priced and timed, with the full catalogue underneath.

Chicago Architecture River Cruise - Buildings to watch for along the route
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Chicago Architecture River Cruise

1.Chicago Architecture River Cruise

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

Cruise Chicago’s river for about 60 to 90 minutes with a live guide, passing landmarks such as the Wrigley Building, Willis Tower, and Marina City. Choose a departure from Navy Pier or Michigan Avenue. The boat has restrooms and a bar, and dogs are welcome. Guides such as Sam, Jim, and Ashley have led especially engaging trips, though the guide varies.

“Must do in Chicago! Tour operators are funny and knowledgeable. Recommend lining up early so you have your pick of the spots. We chose front row and it felt like you were on a private tour.”

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Chicago River 90-Minute Architecture Tour - Following the river past the city’s landmarks
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Chicago River 90-Minute Architecture Tour

2.Chicago River 90-Minute Architecture Tour

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

Board a Wendella boat at the Michigan Avenue Bridge for a 90-minute narrated cruise along all three branches of the Chicago River. An expert local guide connects buildings such as Marina City, the Wrigley Building and Willis Tower to the city’s architectural story. Choose indoor or outdoor seating, and plan for weather: the best open-air views come with exposure to wind and cold.

“Great experience . Definitely would do it again. Trying to get to know me hundred characters and just made it.”

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Chicago River: 1.5-Hour Guided Architecture Cruise - Marina City and the river’s north and south branches
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Chicago River: 1.5-Hour Guided Architecture Cruise

3.Chicago River: 1.5-Hour Guided Architecture Cruise

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

Cruise Chicago’s main river and north and south branches for 90 minutes, passing landmarks from the Wrigley Building to Marina City and Willis Tower. An English-speaking guide brings the skyline’s 130-year story to life, while you choose an open deck or climate-controlled seating. Local drinks and Garrett’s Popcorn are available to buy onboard.

“This cruise is definitely worth doing. John our guide was first class, very funny and entertaining as well as being informative.”

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Chicago: Gangsters and Ghosts Walking Tour - From Millennium Park to the Palmer House
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Chicago: Gangsters and Ghosts Walking Tour

4.Gangsters and Ghosts Walking Tour

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

Walk about 1.5 miles through Chicago’s Loop with a historian, hearing stories of Al Capone, bootleggers, and reported hauntings at places such as the Palmer House and Congress Plaza Hotel. The tour lasts about two hours, with frequent stops and a refreshment and restroom break. A bus upgrade is available, with one stop at Harry Caray’s Italian Steakhouse.

“This was a very interesting and also funny tour! Our guide Tanner was amazing!!! We had a very good time”

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Chicago Architecture Center River Cruise aboard First Lady - Why the docent matters
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Chicago Architecture Center River Cruise aboard First Lady

5.Chicago Architecture Center River Cruise aboard First Lady

★★★★★★★★★★5.0 · 5,536 reviews · 1 hour 30 minutes (approx.) · from $57

Cruise the Chicago River for about 90 minutes aboard Chicago’s First Lady, with live commentary from a Chicago Architecture Center docent. Look for Marina City, Willis Tower, Navy Pier and more while learning how the river and its buildings shaped the city. There’s an enclosed, climate-controlled salon, an open-air deck and a bar onboard.

“This is led by a knowledgable docent from the Chicago Architecture Center do visitors will learn more than on other tours.”

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Chicago: Willis Tower Skydeck and The Ledge Ticket - The elevator ride leads to the main event
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Chicago: Willis Tower Skydeck and The Ledge Ticket

6.Willis Tower Skydeck and The Ledge Ticket

★★★★★★★★★★4.6 · 4,350 reviews · 45 min · from $42

At Willis Tower’s Skydeck, timed entry takes you through Chicago-focused exhibits and a short theater presentation before the 103rd-floor observation deck. Step onto The Ledge, a glass balcony extending 4.3 feet beyond the building, and use the free app’s viewfinder to spot landmarks. Plan for a brief visit, and aim for opening time or after 5 p.m. to reduce crowd pressure.

“What experience , the views are amazing , defo worth the trip out”

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Chicago: Architecture River Cruise Skip-the-Ticket Line - Three branches, one changing view of Chicago
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Chicago: Architecture River Cruise Skip-the-Ticket Line

7.Architecture River Cruise Skip-the-Ticket Line

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

Cruise all three branches of the Chicago River for a close look at landmark buildings such as Marina City, Willis Tower, and Trump Tower. A live guide connects the skyline to Chicago’s architectural history, while a seasonal cash bar offers drinks for purchase. Expect a 75-minute ride in warmer months and a shorter 60-minute trip from November 1 to April 15.

“Love this cruise! Even if you have done it before, you always learn something new!”

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Chicago Crime and Mob Bus Tour - The Biograph Theatre and Dillinger’s last stop
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Chicago Crime and Mob Bus Tour

8.Chicago Crime and Mob Bus Tour

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

The Chicago Crime and Mob Bus Tour takes you from Pearson Street through River North, the Loop, Lincoln Park, and other neighborhoods tied to Chicago crime. An English-speaking guide shares stories of Al Capone, Bugs Moran, John Dillinger, and more, with photo stops at sites such as the Biograph Theatre and a visit to Harry Caray’s mini mob museum.

“Jamie was a great guide, very comedic, informed, prompt, and a great photographer too! It was nice being able to stop and learn about some of the history of Chicago. I highly recommend!”

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Chicago: 360 CHICAGO Observation Deck Ticket - Chicago’s neighborhoods before the skyline
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Chicago: 360 CHICAGO Observation Deck Ticket

9.360 CHICAGO Observation Deck Ticket

★★★★★★★★★★4.5 · 3,173 reviews · 30 min · from $29

At 360 CHICAGO, ride an elevator to the 94th-floor observation deck at 875 N. Michigan for broad views of Chicago and Lake Michigan. The ticket skips the ticket-purchase line, but not security. Explore the Chicago history exhibit and CloudWalk art, stop at CloudBar, and buy the TILT ride separately on site.

“Love the view! It’s worth the money . Love the lounge and sitting areas with great view..”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - Marina City’s corn-cob towers from the water
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Chicago River 45-Minute Architecture Tour from Magnificent Mile

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

★★★★★★★★★★4.5 · 2,924 reviews · 45 minutes (approx.) · from $28

Cruise the Chicago River from the Wrigley Building for 45 minutes of live architecture commentary. You’ll pass the Riverwalk, Michigan Avenue Bridge, Merchandise Mart, Lyric Opera House, and Marina City’s corn-cob towers. Choose an open-air seat or a climate-controlled lounge; guides have included Tess, Zach, Alyssa, and Chris, though the guide varies.

“Great experience. The skyline was beautiful and the tour guide was awesome. This was the highlight of my trip.”

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Chicago Lake and River Architecture Tour - Spot the city-within-a-city buildings
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Chicago Lake and River Architecture Tour

11.Chicago Lake and River Architecture Tour

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

Board Wendella’s boat at the Wrigley Building for a 90-minute cruise along the Chicago River and Lake Michigan. A live guide points out landmark architecture, from the Wrigley Building to Marina City, while you get river-level views and photos of the skyline. Indoor climate-controlled seating and an outdoor deck are available, but spots are first come, first served.

“This was a great tour if you are wanting to many of the buildings and the skyline from the lake. The guide was knowledgeable with the history and construction of the buildings”

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Chicago: 45-Minute Family-Friendly Architecture River Cruise - Guides who make the buildings memorable
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Chicago: 45-Minute Family-Friendly Architecture River Cruise

12.45-Minute Family-Friendly Architecture River Cruise

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

Cruise the Chicago River for 45 minutes, from the Lake Shore Drive area toward Willis Tower and along the South Branch, with live English commentary on the buildings and architects shaping the skyline. You get access to indoor and outdoor decks, climate-controlled seating, and an onboard bar selling local drinks. Sunset trips offer city views in changing light.

“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 - Museum Campus, the river, and Navy Pier
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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

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

★★★★★★★★★★4.0 · 2,191 reviews · 2 hours (approx.) · from $45

Ride a 24-, 48-, or 72-hour Big Bus pass past the Riverwalk, Millennium Park, Navy Pier, and more. Use the app to track buses and find stops, then hop off to explore at your own pace. Digital commentary covers the city, while drivers such as Candace and Felicia have added local tips and personality.

“We loved it. Only thing was that it canceled for Dec 13th we planned on riding it another day for are 24 hrs pass. Candice was bad driver she was a 10 put of a 10”

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Chicago: 1.5-Hour Lake and River Architecture Cruise - The riverfront’s changing skyline
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Chicago: 1.5-Hour Lake and River Architecture Cruise

14.1.5-Hour Lake and River Architecture Cruise

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

Wendella’s 90-minute cruise pairs the Chicago River’s landmark buildings with wide skyline views from Lake Michigan. An English-speaking local guide points out sights such as Marina City, the Wrigley Building, Willis Tower, and the lakefront museums. Choose open-air or climate-controlled seating, and watch the boat pass through the Chicago Lock.

“This was an outstanding tour and I learned a lot about Chicago, a city I grew up by. The architecture as fascinating. I definitely recommend taking the combined river/lake tour. I do recommend that literature about the tour provide recommendations for parking.”

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Chicago Favorites Ultimate Food and Walking Tour - Hot dogs, Italian beef and the art of eating neatly
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Chicago Favorites Ultimate Food and Walking Tour

15.Chicago Favorites Ultimate Food and Walking Tour

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

Walk about 1.25 to 1.5 miles through downtown Chicago with a local English-speaking guide, stopping for deep-dish pizza, a Chicago hot dog, Italian beef, Garrett’s popcorn and a sweet treat. You’ll pass landmarks such as Millennium Park and the Chicago River. The tour lasts about three hours, includes food, and comes with a two-hour bike or kayak rental to use within three days before or after.

“Very fun, informative, and delicious tour of Chicago with our great guide Gabe, who was super personable and humorous. Highly recommend!”

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