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The ones worth booking.
The 15 Chicago tours travellers book more than any others, with the operator, the running time and the real price set out on each one.
Guided Chicago River architecture cruise with live commentary, skyline views, and pet-friendly comfort for one hour to 1.5 hours.
“It was a wonderful experience !! Punctual start, Great guide, lots of information and amazing views!”
A 90-minute guided cruise on the Chicago River with close skyline views, indoor warmth options, and $45 guided architecture stories.
“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”
A 1.5-hour Chicago architecture cruise with expert guides, open-air or climate-controlled seating, and local cash-bar snacks.
“The Chicago river cruise was a fun activity. Elisa, the tour guide, did a good job informing and entertaining us on Chicago architectural history. There was also a climate controlled bar for those who feel cold in the middle of the cruise.”
Chicago Loop tour mixing gangster history and ghost stories with a historian guide, iconic stops, and optional minibus upgrade for $52.
“Taka was our guide and she was fantastic. We had such a good time, she was a very good story teller, loud and clear. Lots of interesting information. We learned alot and had a lot of fun.”
Chicago Architecture Center’s First Lady river cruise shows Willis Tower, Marina City, and more in 90 minutes with live docent commentary.
“I’m really glad I took the tour. It’s a great way to spend 90 minutes if you want to learn more about Chicago during a short trip. The guide was fantastic, she knew so much about Chicago’s history, especially the river, the bridges, and the buildings. The bar was great too: warm and cosy, and…”
Step onto Willis Tower’s glass **The Ledge** for skyline views, Chicago-themed exhibits, and a tight, efficient 45-minute visit with timed entry.
“Very well organised and very few people actually visiting the experience (Feb 11th)….so no queuing! You walk through an interesting history segment first and then after some more photo opportunities enter the lift upto the Skydeck. The day we went was gloriously sunny and the view was spectacular. The Ledge was really weird at first…”
Skip the ticket line for a 60–75 minute Chicago architecture cruise across all three river branches with live narration and optional cash-bar drinks.
“this tour was really nice, enjoyed very much, tour guide was great 😁”
Ride Chicago’s mob route by coach with a lively guide, great photo stops, and quick visits tied to Al Capone and John Dillinger.
“Incredibly interesting and such a cool tour!! Our tour director Maddie is a fantastic story teller and it was so cool to learn who all these people were. 2nd time in Chicago and learned more on this tour than anything else! Highly recommend!”
Skip the line at 360 CHICAGO. Ride up fast to the 94th-floor deck for skyline views, CloudBar, CloudWalk, and optional TILT.
“So worth every penny! Please go atleast 30 mins earlier, people get there super early”
45-minute Chicago River architecture cruise from the Magnificent Mile with live guide narration, great photo angles, and climate-controlled comfort.
“Lots of information. You can stay inside downstairs or be up on the deck to look up at the buildings. Just the right length of tour. Very convenient.”
Skip the ticket desk and ride up 1,000 feet in 40 seconds for 360° Chicago skyline views, Lake Michigan sights, and optional TILT.
“Great views of Chicago in every direction. Would definitely recommend as a must-do when visiting this fabulous city!”
Cruise Chicago’s river and Lake Michigan for 90 minutes of live architecture narration, skyline views, and landmark spotting from Wendella.
“Very informative. Bring a small blanket- it was chilly. But if you’re hot, you could sit on the blanket. The chairs were pretty uncomfortable.”
A 45-minute Chicago River architecture cruise with live family-friendly narration, indoor and outdoor decks, and a cash bar. From $28.
“The tour and the guide were fantastic. Everything was clear and engaging, we didn’t even notice the time flying by. As a small extra, having an audio guide in other languages would be a great addition.”
A flexible open-top Chicago bus pass that covers the big sights fast, with digital commentary, frequent hop-on stops, and easy app tracking.
“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.”
Cruise Chicago’s architecture by river and Lake Michigan in 90 minutes, with expert guides, Chicago Lock passage, and deck or indoor seating.
“I really liked the detailed explanations he gave about the view of the city from Lake Michigan and the various buildings seen from the Chicago River.”
