USA · TOURS IN CHICAGO

The 15 Best Chicago Tours & River Cruises

73 tours  ·  from $24 a head

The architecture cruise is the one nobody regrets, and the rest of the city is a good walk. These 15 cover the river boats, the skydecks, the gangster walks and the food, priced and timed, with a note on which run through winter.

Chicago Architecture River Cruise - The skyline from the Chicago River
Cruises & Boat Tours, Tour Reviews, Tours in Chicago

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 with an architecture guide, passing the Wrigley Building, Tribune Tower, Hancock Center, Willis Tower, Marina City, and Aqua. Choose a Navy Pier or Michigan Avenue departure, then enjoy live commentary, skyline views, a restroom, and a full bar. Dogs are welcome, but winter passengers should dress warmly.

“The cruise was fun but could not hear the tour guide over the many screaming babies on board. The tour operators should consider a minimum age requirement. Boat was clean and drinks were great! Crew friendly too.”

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Chicago River 90-Minute Architecture Tour - Finding Wendella at the Michigan Avenue Bridge
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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

Spend 90 minutes cruising Chicago’s three river branches with a trained guide and views of more than 130 years of architecture. Wendella boats offer indoor climate-controlled seating, an open upper deck, restrooms, snacks, and drinks. Guides such as Lucas, Jack, and Alyssa have earned praise for clear, funny narration.

“It's tricky locating your your because different companies get booked thru Viator, and their contact info is not obvious. Learn your provider in advance for your best chance at catching your tour boat. Ours was Wendella; and it was AMAZING. My hubby and I took the 90 min, 3 river architecture boat tour.”

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Chicago River: 1.5-Hour Guided Architecture Cruise - Boarding near the Michigan Avenue 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

Spend 90 minutes with Wendella Tours & Cruises tracing Chicago’s architectural story from the Michigan Avenue Bridge to the river branches. Guides such as John, Sarah, Alex, and Scotty D mix building facts with humor. Choose an open deck or climate-controlled seating, and buy local beer, spirits, and Garrett Popcorn onboard.

“Only option for us on the boat was at the front and it was very hard to hear the guide at times.”

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Chicago: Gangsters and Ghosts Walking Tour - Millennium Park and the Bean
Ghost, Cemetery & Haunted History Tours, Tour Reviews, Tours, Tours in Chicago, Walking Tours

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 Prohibition-era stories and ghost tales at Millennium Park, Palmer House, the Riverwalk, Chicago Theatre, and Congress Plaza Hotel. Guides such as Taka, Sophia, Tanner, and Avery bring clear, engaging storytelling. A minibus upgrade is available.

“Avery our tour guide was great. Highly recommend while visiting Chicago. Light walking and nice stops.”

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Chicago Architecture Center River Cruise aboard First Lady - Boarding, seating, and choosing your best view
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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

Spend 90 minutes aboard Chicago’s First Lady with a Chicago Architecture Center docent explaining the river, skyscrapers, bridges, and city planning. You’ll see Marina City, Willis Tower, Navy Pier, 150 North Riverside, and more from the water. Choose an open-air seat or the climate-controlled salon, and arrive 30 minutes early for first-come seating.

“This was a great tour aboard the First Lady, and the docent, who was a volunteer from the Chicago Architecture Center, was so knowledgable and gave a great tour. He gave the history of Chicago and its architecture and the tour provided a chance for pictures at choice locations. There was plenty of room on the boat. I would highly recommend this tour. Well worth it!”

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Chicago: Willis Tower Skydeck and The Ledge Ticket - Finding the entrance on South Wacker Drive
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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 Willis Tower’s 103rd-floor Skydeck for sweeping views across Chicago and up to four states. Walk onto The Ledge, a glass balcony extending 4.3 feet beyond the tower, then explore exhibits on Chicago’s fire, architecture, neighborhoods, food, and famous faces. Timed entry helps manage crowds, though your photo time on The Ledge is brief.

“Willis Tower and The Ledge offer an unforgettable experience with stunning panoramic views of Chicago. Stepping onto the glass floor of The Ledge is both thrilling and surreal. A must-visit for anyone looking to see Chicago from a breathtaking perspective!”

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Chicago: Architecture River Cruise Skip-the-Ticket Line - The boarding process and the first view 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

You will cruise all three branches of the Chicago River for 60 to 75 minutes, with a live English or Spanish guide explaining about 40 buildings, from Marina City and Trump Tower to Willis Tower. Guides such as Chicago Bob, Jeremy, Juan, and Kevin add humor and local color. A cash bar is available 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 guides make or break the ride
Tour Reviews, Tours, Tours in Chicago

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

Ride a climate-controlled coach through Chicago’s mob-era neighborhoods with guides such as Jay, Dane, Jamie, and Sophia. Hear stories about Capone, Dillinger, Bugs Moran, and Frank Nitti, stop at the Biograph Theatre and Harry Caray’s vault, and visit the St. Valentine’s Day Massacre site. The tour lasts about 90 minutes to two hours.

“Really fun history of Chicago. Nice thing to do and experience especially on a cold day! Helps you see another side of the Windy city!”

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Chicago: 360 CHICAGO Observation Deck Ticket - Chicago stories 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

Ride one of North America’s fastest elevators to the 94th floor of 875 N. Michigan for wide views over Chicago, Lake Michigan, and four states. You’ll explore a renovated concourse, CloudWalk art, CloudBar, and the Magnicity app. TILT is optional and must be added on site.

“amazing experience staff superb and the views were incredible”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - Picking the right deck for Chicago weather
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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 from the Magnificent Mile along the Chicago River for 45 minutes, with live commentary on the Wrigley Building, Riverwalk, Merchandise Mart, Lyric Opera, and Marina City. Guides such as Tess, Zack, and Chris have earned praise for clear, funny presentations. Choose open-air views or a climate-controlled lower deck.

“It was a nice ride, beautiful views the tour guide explained the history of the buildings and it was about a 45 minute ride”

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Chicago Lake and River Architecture Tour - The Buckingham Fountain of the river corridor
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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

Spend about 90 minutes with Wendella Tours & Cruises, leaving from the Wrigley Building at 400 N Michigan Avenue. A live guide such as John, Kenny, Tess, or Lucas explains Chicago’s famous buildings as you travel the river and Lake Michigan. Choose indoor or outdoor seating, arrive early for the best view, and bring a jacket for the windy lake.

“The Chicago Architecture River and Lake Tour is a must for visitors, as well as locals. We had a great time, and our guide Justin was excellent!”

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Chicago: 45-Minute Family-Friendly Architecture River Cruise - The route from Michigan Avenue 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 the Chicago River for 45 minutes with a live English-speaking guide, passing the Wrigley Building, Chicago Riverwalk, South Branch, and Willis Tower. Choose an open-air deck or climate-controlled cabin, and time your ride for sunset or evening city lights. Guides such as Kenny, Zach, and Alyssa keep the architecture stories lively for adults and children.

“It was nice and short. I liked how they hit the highlights. Love the view from the pier”

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - Stop 2: Willis Tower and Skydeck Chicago
Tour Reviews, Tours, Tours in Chicago, Trolley & Hop-On Hop-Off Tours

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

See Chicago from an open-top double-decker bus on a 24, 48, or 72-hour pass covering the Riverwalk, Millennium Park, Navy Pier, Museum Campus, and the Magnificent Mile. Use the app for live bus tracking, ride the full two-hour loop, or hop off to explore. Digital commentary is included, with optional self-guided walking tours.

“My husband and I enjoyed the big bus tour. It was very convenient in the winter with the snow. The bus was covered so you were protected from the cold and wind. Also they provided headphones so you could listen to the audio tour.”

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Chicago: 1.5-Hour Lake and River Architecture Cruise - Starting near the Wrigley Building
Cruises & Boat Tours, Tour Reviews, Tours in Chicago

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. An English-speaking guide such as Lucas, Sarah, Jack, or Kenny explains Chicago’s architecture with facts and humor. Choose an outdoor deck or climate-controlled cabin, and bring snacks or buy drinks aboard.

“The guide knew every bit of information about the city architecture, I was mesmerized about it all! It was brilliant!”

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Chicago Favorites Ultimate Food and Walking Tour - The Chicago hot dog is a lesson in local rules
Food, Food & Drink, Tour Reviews, Tours, Tours in Chicago, Walking Tours

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 while tasting deep-dish pizza, a Chicago hot dog, Italian beef, Garrett popcorn, and a brownie or gelato. Guides such as Gabe, Fran, Jessika, and AJ mix food with architecture and local stories. A two-hour bike or kayak rental is included for use near your tour date.

“It wss a great experience. MJ knows his stuff. The food is good at nice places. It was better than expected.”

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