The 15 Best Chicago Tours & River Cruises

1.Chicago Architecture River Cruise

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

See Chicago’s skyline from the river, hear lively architecture stories, and visit multiple branches on this practical one-hour cruise.

“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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2.Chicago River 90-Minute Architecture Tour

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

Cruise all three branches of the Chicago River for 90 minutes of architecture, stories, skyline views, and practical city history.

“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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3.Chicago River: 1.5-Hour Guided Architecture Cruise

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

Chicago’s 90-minute river cruise pairs skyline views with lively architecture stories, open-air seating, climate control, and a cash bar.

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

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4.Gangsters and Ghosts Walking Tour

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

Explore Chicago’s gangster past and ghost stories on a historian-led Loop walk covering Al Capone, haunted hotels, Death Alley, and more.

“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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5.Chicago Architecture Center River Cruise aboard First Lady

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

See Chicago’s skyline from the river on a 90-minute First Lady cruise with Chicago Architecture Center docents, indoor seating, and a full bar.

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

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6.Willis Tower Skydeck and The Ledge Ticket

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

Review of Chicago’s Willis Tower Skydeck and The Ledge, with practical tips on views, timing, crowds, exhibits, price, and photo time.

“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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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, hear lively architecture stories, and see landmarks from a comfortable boat for $39.

“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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8.Chicago Crime and Mob Bus Tour

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

Ride through Chicago’s mob past, from the Biograph Theatre to Nitti’s vault, with lively guides, crime scenes, and winter comfort.

“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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9.360 CHICAGO Observation Deck Ticket

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

See Chicago from 1,000 feet at 360 CHICAGO, with fast elevator access, Lake Michigan views, CloudBar, and optional TILT.

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

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

See Chicago’s riverfront icons on a 45-minute architecture cruise with live narration, indoor shelter, open-air views, and excellent value.

“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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11.Chicago Lake and River Architecture Tour

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

Cruise Chicago’s river and Lake Michigan shoreline for skyline views, lively architecture stories, indoor seating, and excellent photo stops.

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

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12.45-Minute Family-Friendly Architecture River Cruise

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

See Chicago’s skyline from the river on a 45-minute family cruise with live architecture commentary, indoor seating, and sunset views.

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

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

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

See Chicago’s top sights from an open-top Big Bus, with flexible 24, 48, or 72-hour passes, audio commentary, and live bus tracking.

“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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14.1.5-Hour Lake and River Architecture Cruise

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

See Chicago’s landmark buildings from the river and lake on a lively 90-minute cruise with expert guides, open-air decks, and skyline views.

“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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15.Chicago Favorites Ultimate Food and Walking Tour

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

Taste Chicago classics, hear Loop stories, and see Millennium Park on a relaxed three-hour food walk with a free bike or kayak rental.

“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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