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The 15 Best Chicago Tours & River Cruises

73 tours  ·  from $24

Chicago invented the skyscraper and then built a river through the middle of them to look at it from. These 15 cover the architecture cruises, the gangster walks and the deck tickets, priced and timed.

Chicago Architecture River Cruise - Chicago’s architectural turning points
Boat Tours in Chicago, Chicago Tours, Cruises & Boat Tours, Tour Reviews

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 the Chicago River with an expert guide, passing the Wrigley Building, Willis Tower, John Hancock Center, Marina City, and more. Choose a Navy Pier or Michigan Avenue departure, enjoy onboard restrooms and a full bar, and bring your dog along. Expect a 60 to 90-minute ride, depending on the season and option.

“When booked they said there was a below deck to stay warm from the extreme cold in Chicago. Only flaps cover window below. It was freezing from the temperature and wind. They sold merch to warm peeps. For example flimsy blanket and gloves. Which looked like they were from the dollar store. The tour guide spoke so fast we lost interest after 12-15 minutes because we couldn’t understand him. We spent first 20 minutes asking each other what he said. Sounded like reading from a script. No fun facts no humor, no nuggets we could tell people about. Finally we gave up and turned on football game from our device.…”

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Chicago River 90-Minute Architecture Tour - Finding Wendella at the Wrigley Building
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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 Wendella at the Wrigley Building for a 90-minute cruise through all three branches of the Chicago River. An expert guide explains Chicago’s architecture as you pass Marina City, Willis Tower, Merchandise Mart, the Riverwalk, and more. Choose climate-controlled indoor seating or an open-air upper deck.

“So cold in winterX dont suggested and please make it in summer time, i cant enjoy it at all because my fingers and toes felt nothing and i went to the indoor lower deck after one hour on the upper outdoor upper deck”

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Chicago River: 1.5-Hour Guided Architecture Cruise - Setting out from the DuSable Bridge
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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 with guides such as John, Sarah, Alex, and Scotty D. See the Wrigley Building, Marina City, Willis Tower, Aqua, and more from open-air or climate-controlled decks, with local drinks and Garrett Popcorn available onboard.

“Unreal tour guide, super knowledgeable. Stunning views, great day out.”

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Chicago: Gangsters and Ghosts Walking Tour - Starting in the Loop: speakeasies, tunnels, and mob headquarters
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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 guide, hearing true crime tales and ghost stories tied to the Palmer House, Riverwalk, Chicago Theatre, and Congress Plaza Hotel. Guides such as Taka, Sophia, Tanner, and Avery are known for clear storytelling. A minibus option is also available.

“The guide had a loud voice so everyone could hear and she spoke fast and clear. The tour was interesting, so happy I booked it”

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Chicago Architecture Center River Cruise aboard First Lady - The Chicago Architecture Center connection
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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 90 minutes aboard Chicago’s First Lady while a Chicago Architecture Center docent explains the city’s buildings, bridges, and past. You’ll pass Marina City, Willis Tower, Navy Pier, and 150 North Riverside. Cynthia, Laura, Amy, Russell, Nick, and Mark are among the guides praised for lively talks.

“Evening was the perfect time to view the architecture along the river and Amy was a great tour guide.”

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Chicago: Willis Tower Skydeck and The Ledge Ticket - The fast ride to the 103rd floor
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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

Visit the 103rd-floor Skydeck at Willis Tower, walk onto The Ledge’s glass balconies, and explore Chicago exhibits on the way up. Your timed ticket includes the observation deck, theater presentation, WiFi, and a viewfinder app. Allow about 45 minutes, or longer if lines are light.

“It was super fun! The museum was cool to walk through, the views were incredible and standing on the ledge was definitely a once in a lifetime experience.”

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Chicago: Architecture River Cruise Skip-the-Ticket Line - What you see from the boat
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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

Join Shoreline Sightseeing for a 75-minute Chicago architecture cruise, or 60 minutes from November 1 to April 15. A live guide such as Chicago Bob, Juan, or Jeremy points out about 40 landmark buildings while you ride all three river branches. A cash bar operates on most boats.

“The tour leader was very knowledgeable about the history of Chicago from a waterfront viewpoint. He had the audience entertained as the we caught the beautiful sunset. This tour is a MUST.”

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Chicago Crime and Mob Bus Tour - The Biograph Theatre and John 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

Board a climate-controlled coach at 163 E. Pearson Street for a 1.5 to 2-hour tour of Chicago’s crime past. Guides such as Jay, Dane, Jamie, and Sophia share stories of Capone, Dillinger, Bugs Moran, and more, with photo stops at the Biograph Theatre and Harry Caray’s mob museum.

“Very informative. Harry Caray’s place was awesome. The different stops were really cool as well. I would recommend to anyone interested in Chicago crime history.”

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Chicago: 360 CHICAGO Observation Deck Ticket - The lower concourse sets the scene
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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

Ride one of North America’s fastest elevators to the 94th floor of 875 N. Michigan for wide views of Chicago, Lake Michigan, and four states. Explore the lower concourse exhibits, CloudWalk art, CloudBar, and the Magnicity app. TILT is optional and costs extra on site.

“This was so much fun to see the whole city and have a romantic drink at the beautiful bar! They have great souvenirs for sale and the Tilt experience looked fun but I didn't try it myself. Our bartender (can't remember her name) was on point with her service and added some personality and humor to the night, she even recommended our dinner spot which was excellent (Doc B's)!! I love the top of the Hancock - it's iconic Chicago and Cloud Bar 360 is worth the price! The souvenir photos (order and pay to take home) they take of you when you walk in are super cute too!! Highly…”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - Choosing between the upper and lower decks
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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 Chicago’s main river and part of the south branch for 45 minutes with live commentary from guides such as Tess, Chris, Zach, or Alyssa. See the Wrigley Building, Riverwalk, Merchandise Mart, Lyric Opera, and Marina City from the water, with indoor seating and a bar onboard.

“Chris was so much fun! He was very informative ! My friends and I booked this experience during the freezing cold and he was such a trooper ! We had so much fun !”

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Chicago Lake and River Architecture Tour - Boarding at the Wrigley Building
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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 at Wendella’s Michigan Avenue dock for a 90-minute cruise along the Chicago River and Lake Michigan. A live guide such as John, Kenny, Tess, or Lucas explains the city’s famous buildings, while indoor and outdoor seating, restrooms, and a bar make the ride easy in changing weather.

“Great experience. Tour guide was extremely knowledgeable and funny. Highly recommend going thru the locks and onto Lake Michigan.”

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Chicago: 45-Minute Family-Friendly Architecture River Cruise - From Lake Shore Drive to Willis Tower
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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 from Lake Shore Drive toward Willis Tower and back with an English-speaking guide, open-air and climate-controlled decks, and Chicago beer, spirits, snacks, and hot drinks available to buy. The 45-minute route suits families, with children under four riding free.

“Well managed, knowledgeable and witty guide, comfortable ride, value for money”

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - Grant Park and the city’s open space
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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

Use a 24, 48, or 72-hour Big Bus Chicago pass to explore 11 stops from the Riverwalk and Willis Tower to Navy Pier and the Magnificent Mile. Ride the full two-hour loop, hop off at museums and parks, and use the app for live bus locations, route details, and self-guided walks.

“Pros Frequent busses, Good route around downtown Nice interior Friendly staff Reasonable prices Cons Limited commenting on architecture and surrounding places Seats were slippery and not comfortable Some got hit by tree branches in upper deck”

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Chicago: 1.5-Hour Lake and River Architecture Cruise - Starting beneath the Wrigley Building
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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

Cruise from Michigan Avenue up the Chicago River, through the Chicago Lock, and onto Lake Michigan. Guides such as Lucas, Kenny, Jack, and Sarah bring Chicago’s architecture to life, while you enjoy open-air or climate-controlled seating, restrooms, and a cash bar.

“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 - Evening route: Gino’s East, the Water Tower, and city lights
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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 1.5 miles through Chicago’s Loop with an English-speaking guide such as Gabe, Fran, Jessika, or Kevin. Taste deep-dish pizza, a Chicago hot dog, Italian beef, Garrett popcorn, and a brownie or gelato, then use the included two-hour bike or kayak rental within three days.

“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!”

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