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“Unreal tour guide, super knowledgeable. Stunning views, great day out.”
Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.
“Great experience with Alan, he was so good at explaining everything and had loads of info and knowledge to share”
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.
“Really enjoyed our guide Joel's enthusiasm and love for the museum and Chicago. Learning the milestones of the museum's collecting its most famous collections and pieces, and the stories behind them was fascinating. Well worth the 2.5 hour tour!!”
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.
“Got a great macro and micro view of the Art Institute with our trusty guide Heath. It was perfect in pace, depth, and tone.”
90-minute Chicago River sunset cruise with included cocktails, award-winning architecture commentary, and 100-year-old bascule bridges.
“Complimentary water/coffee/lemonade and availability of adding on alcoholic drinks is nice. Great tour guide & architectural info.”
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.
“Funny tour guide. Gave a lot of information. Great tour. They drove by many attractions and had good stories for it.”
90-minute Chicago River architecture cruise with expert narration, open-air top deck views, and free coffee, lemonade, snacks. $57.
“The tour said snacks included but when we asked they said they ran out of snacks (cookies). Good thing they still have the drinks.”
A 2-hour private Art Institute tour with skip-the-line access, an expert guide, and major masterpieces tailored to your interests in Chicago.
“Joe was an amazing guide. Informative and very interesting! Explained the history of the artist as well as the painting.”
Sunset views from Chicago’s open-top bus: Museum Campus skyline, Millennium Park, Art on the Mart, and a live English guide.
“Very good 🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝🔝✈️✈️✈️✈️✈️✈️✈️😀💓😀💓💓💓💓✈️✈️✈️✈️✈️✈️✈️✈️✈️✈️✈️✈️✈️✈️✈️😀😀💓💓”
Skip-the-line Art Institute tour: enter 30 min early, see Picasso and Hopper with an expert, satisfaction guaranteed, $90.
“Great. All went well. Excellent museum artefacts, knowledgeable guide and very nice people in the group- you can’t ask for more.”
2-hour guided street art walk in Wicker Park, Bucktown, and Logan Square. Learn artists stories and watch art made in real time.
“Très belle marche pour découvrir d'autres quartiers de la ville ainsi que l'art de la rue. Merci!”
A private custom walking tour of Chicago with a local guide, flexible route, museum exteriors focus, and practical city advice for your day.
“El Guia tenia buena voluntad, pero falto de motivacion, iniciativa y conocimientos...esperabamos algo mas que un paseo con poco contenido de historia y anecdotas...”
Downtown Chicago TV and movie sites walking tour: Willis Tower, Auditorium Theatre, Ocean’s 11, The Dark Knight, and more in 2 hours.
“ABSOLUTE WORSE ........ First they NEVER notified me that the pickup and dropoff had changed. I had to call 5 minutes before the tour was to leave because no one showed up at the Meeting Place and was told everyone was notified by email and when I told her that we had not been notified…”
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.
