America · CHICAGO TOURS
The shortlist to send a friend: 15 chicago tours worth the money, each with its price, its traveller verdict and the thing to know before you pay.
See Chicago’s famous buildings from the Chicago River on a guided architecture cruise with live commentary, restrooms, and pet-friendly fun.
“The tour guide was great! Loved his insight, knowledge, and personality. It wasn’t always easy to hear him as other passengers We’re on their phones or talking to each other loudly.”
A 90-minute Chicago River architecture cruise with Wendella, expert narration, and great views of Marina City, the Wrigley Building, and more.
“Loved loved this tour ! So much history and a funny host!! Really enjoyed hearing all about Chicago’s history and the history of the river ! Great views and lots to see !”
Skip the line for a 90-minute Chicago River architecture cruise with expert guides, indoor or open-deck seating, and a cash bar.
“Great way to see another view of the city. Our Guide Sarah was very knowledgeable. She clearly loves her job.”
A 2-hour Loop walk with a historian, gangster lore, and ghost stories at real downtown landmarks, plus an optional minibus upgrade.
“Very exotic experience, another good way to know about Chicago history beside just regular tourist spots”
Chicago Architecture Center River Cruise aboard First Lady: 90 minutes of docent-led skyline storytelling, comfort on two levels, and skyline photos by the river.
“Yes please, add to Cart. Amazing history lesson and current affairs in the city of Chicago. This was a fantastic tour with an incredibly knowledgeable docant. And they have a bar on the boat for the win.”
Willis Tower Skydeck and The Ledge ticket with timed entry, Chicago exhibits, and a glass balcony view from 103rd floor.
“We had so much fun, I love sky deck this is my fourth time’s going there.”
Skip the ticket line on a Chicago River architecture cruise covering all three branches with live docent narration and a cash bar.
“It was a lovely tour and all employees were professional and friendly. Really enjoyed the Chicago architecture tour!”
Chicago mob bus tour with coach views, photo stops, Biograph Theatre and St. Valentine’s Day Massacre sites, plus a mini mob museum.
“Lots of great info and stops bring it all to life. Recommend highly. Our guide was full of extra tidbits and interactive.”
360 CHICAGO lifts you 1,000 feet above Michigan Avenue for 30 minutes of skyline and Lake Michigan views, plus the TILT upgrade.
“Super fun. I recommend buying the observation deck/tilt/sip ticket ahead of time, rather than a la carting when you get there. This would have saved us some money.”
A 45-minute Chicago River architecture cruise with live English narration, great views from top or covered decks, and strong value at $28.
“The tour was very interesting and I would highly recommend. We went in early January and it was absolutely freezing. If I were doing it again I would stay in the lower climate controlled area then come out to take pictures near the end of the tour.”
A 90-minute Chicago architecture cruise with live narration on the river and Lake Michigan shoreline views from Wendella.
“This experience was really great! What made it Fun and Exciting was the commentator telling us all about the history of Chicago architecture. John was really funny and had the crowd laughing. If you take this tour, go with John.”
45-minute Chicago River architecture cruise with live guide, indoor and outdoor decks, skyline views, and cash bar snacks and drinks at $28.
“Sarah was a great guide with a lot of interesting facts about the Chicago architecture. The 45 minute tour was just enough time to get a feel for the history of the city. The boat was comfortable and there were lots of seats for the guests. Highly recommend this tour.”
Big Bus Chicago hop-on hop-off pass covers downtown icons like Millennium Park and Navy Pier, with audio, frequent buses, and flexible 24 to 72 hours.
“Audio poor. Only one driver explained things. Some staff were crabby. It was a nice way to see the city. Gave coupons for ice cream but didn’t tell us where the ice cream museum was to get some. Would say it was good way to see city so worth in that way. Expensive for what you got.”
A 90-minute Chicago River and Lake Michigan architecture cruise with expert guide, Chicago Lock passage, and deck or climate seating for $44.
“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.”
Eat Chicago classics on an easy 3-hour Loop walk, see Millennium Park and the Pedway, then use a free 2-hour bike or kayak.
“Go hungry, plenty to eat. Our Tour guide was funny, entertaining, and very knowledgeable about Chicago.”
Every kind of day out, and the best of each.
