CHICAGO · ILLINOIS
The best of Chicago.
The 15 best guided tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Chicago River 1.5-hour architecture cruise covers main stem plus north and south branches. Expert guides, indoor comfort, deck views.
Most Popular“Our tour guide was superb! He was knowledgeable and funny! Great experience! Highly recommend the Chicago River 1.5 hour Guided Architectural Cruise!!!”
Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.
“It was a fun and interesting tour. Baylor was a great and entertaining guide.”
A dark, hands-on Medieval Torture Museum visit in Chicago with an audio guide and a ghost-hunting app for extra chills.
“Super interesting facts brought to you in a wonderfully interactive way. Loved the visual displays with the interactive audio and signs.”
2-hour small-group Segway tour of Chicago from $65. Learn fast, glide past Millennium Park, Buckingham Fountain, Museum Campus, and the lakefront.
“Mike was a great guide!! His instructions were clear, we felt comfortable on the segways right away. Mike's stories were interesting and funny. He took us to some really cool spots. We'll do this again!”
Skip-the-line small-group tour at the Art Institute of Chicago with admission included. See Van Gogh, Hopper, Warhol, and more in 2.5 hours.
“Our guide Joel was amazing! He was very knowledgeable and engaging. The museum is one of the best I’ve seen. It is a can’t miss if you are in the city. Worth every penny!”
Private Art Institute of Chicago skip-the-line guided tour with an expert guide, smart pacing, and a 2.5-hour route through major works.
“Mandy aka Amanda was very knowledgeable and amazing. She was flexible and answered all questions people had. She also gave us few minutes to explore in each room, which I really appreciated.”
90-minute Chicago River sunset cruise with included cocktails, award-winning architecture commentary, and 100-year-old bascule bridges.
“Perfect date night. Friendly staff and beautiful scenery.”
A live-guided sunset ride on a Chicago open-top bus, with night skyline views, Navy Pier to the Loop, and photo stops plus easy downtown logistics.
“BRING A JACKET! Driving down the highway with no roof proved to be extra chilly. Pack something warm just in case. Great for older folks who can’t do walking tours.”
90-minute Chicago River architecture cruise with expert narration, open-air top deck views, and free coffee, lemonade, snacks. $57.
“Jim did an amazing job with the tour guiding! Very informative and clearly passionate about the architecture along the river! The rest of the crew were extremely friendly and helpful, too! Thanks for an amazing river tour!”
A 2-hour private Art Institute tour with skip-the-line access, an expert guide, and major masterpieces tailored to your interests in Chicago.
“Our guides Mark and Michelle were knowledgeable and personable! We learned a lot about the art and had a wonderful time!”
Sunset views from Chicago’s open-top bus: Museum Campus skyline, Millennium Park, Art on the Mart, and a live English guide.
“Not very excited, definetely overpriced, the tour guide was not respectful. Also forgot an expensive scarf on the bus, the stuff even did not try to locate me although the guide asked me where I was from, what hotel I was staying in and what conference I have attended.”
Skip-the-line Art Institute tour: enter 30 min early, see Picasso and Hopper with an expert, satisfaction guaranteed, $90.
“Joe was knowledgeable and very enthusiastic. Great tour. Good with kids.”
2-hour guided street art walk in Wicker Park, Bucktown, and Logan Square. Learn artists stories and watch art made in real time.
“Savoir, explication, intelligence, pointure dans son sujet…. Très bon ! Je recommande!!”
A private custom walking tour of Chicago with a local guide, flexible route, museum exteriors focus, and practical city advice for your day.
“Visite agréable avec guide parlant bien le français… aurions aimé un peu plus d’explications culturelles.”
Downtown Chicago TV and movie sites walking tour: Willis Tower, Auditorium Theatre, Ocean’s 11, The Dark Knight, and more in 2 hours.
“Fun and interesting, the tour gives lots of tidbits from history and from some of your favorite films.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
