Chicago · TOUR REVIEWS
Three days or a long weekend, the problem is the same: one lakefront, one river, and far more city than fits. The 15 below are the days out that earn their place, priced and timed, with the full catalogue underneath when you want to dig further.
See Chicago’s skyline from the river on a guided architecture cruise with expert stories, famous buildings, onboard restrooms, and flexible departure times.
“The host of the tour was great! He was very informative and knowledgeable about the city's history. Also, we had great views of the buildings and were able appreciate the beauty of the architecture.”
Cruise all three branches of the Chicago River, hear lively architecture stories, and see icons including Marina City and the Wrigley Building.
“Well worth the trip. Learned so much about Chicago and the stories behind its architecture. We definitely recommend this during your trip.”
Cruise Chicago’s main, north, and south river branches while expert guides explain 130 years of landmark architecture.
“The tour guide was super engaging and there was a lot of good information. Would definitely recommend.”
Explore Chicago’s Loop through true gangster tales, Al Capone sites, haunted hotels, and ghost stories on a lively two-hour walking tour.
“It was a very cold, windy Chicago night but the tour guide braved it out so we did too--and so glad we did! It was interesting listening to all of the stories about Chicago while wallking around the streets at night. We really enjoyed the tour but will never swim in the water in and around Chicago! Lol”
See Chicago’s landmark towers from the river, with expert architecture guides, open-air views, a heated salon, and a full bar onboard.
“Great experience. So much information was shared about every skyscraper that are build along the riverwalk. The views alone is worth to book this cruise experience.”
Step onto the glass Ledge at Chicago’s Willis Tower for wide city views, hands-on exhibits, and a fast, thrilling look from the 103rd floor.
“Well organised, queues are kept moving and enough time allowed on the ledge”
Cruise all three branches of the Chicago River, hear lively architecture stories, and see skyline icons from a comfortable sightseeing boat.
“This was a great tour. We went in the 8pm cruise and we were able to enjoy a beautiful sunset and then see the buildings lit up. We also got to experience some perfectly timed nighttime features, like building projections and fireworks because of the time we choose. Our guide Brian was great; entertaining and clearly loves his city. Will definitely do this again.”
Explore Chicago’s mob past by coach, with Al Capone sites, the Biograph Theatre, St. Valentine’s Day Massacre site, and Nitti’s vault.
“Great tour guide! Windows of bus were fogged, couldn’t see anything but stories were great! Good length but they need to fix the windows in winter with fogging!”
See Chicago from 1,000 feet at 360 CHICAGO, with skyline and lake views, neighborhood exhibits, CloudBar, 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 for 45 minutes of architecture, live stories, skyline views, indoor shelter, and a smart $28 price.
“The tour was great cold 🥶 but great. Tour was funny and knowledgeable. I would recommend in the warmer months.”
Cruise Chicago’s river and lakefront for 90 minutes of architecture, skyline views, live stories, indoor seating, and practical tips for $45.
“A lot of information in a short time. The guide talked very fast. People were standing blocking the view”
See Chicago’s skyline from the river on a 45-minute family cruise with live architecture stories, indoor seating, open decks, and sunset views.
“Loved it. Great way to see the city. Excellent commentary.”
See Chicago’s top sights from an open-top double-decker bus, with flexible 24, 48, or 72-hour passes and live tracking.
“Easy way to get around and see the city. The app gives you a general idea where the buses are so you can time your stops and reboarding.”
Cruise Chicago’s river and lakefront for 90 minutes of architecture, skyline views, expert stories, and a passage through the historic lock.
“I enjoyed the tour and had a great time on Chicago River and Lake Michigan. The tour guide was great and told us a lot of interesting facts about the architecture and about important people or the history of the city in general. The length of time was perfect and I would definitely recommend to go on this tour.”
Taste Chicago classics, see Loop landmarks, and learn local stories on a three-hour food walk with a free bike or kayak rental.
“This is tough! Our tour guide Fran was absolutely amazing and had great energy, but I’m not sure I would recommend this food tour. My family and I did the Architecture Boat Tour the day before and this shared the same concept- they both had the same exact information, so that became very repetitive. The food itself was also OK. Nothing amazing or worth wild so we were all a bit disappointed because a lot of the reviews said, it’s the best!”
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