Chicago · GUIDED
The 15 best guided tours you can book today, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.
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 gangster past and ghost lore on a historian-led South Loop walk through Death Alley, the Riverwalk, and haunted hotels.
“Sophia was very informative and very friendly! Was a last minute book and we enjoyed it, especially the Palmer brownie!”
Explore Chicago’s Medieval Torture Museum with realistic displays, an audio guide, hands-on exhibits, and a ghost-hunting app.
“What a unique museum in the city of Chicago. Fun yet gruesome experience. Thanks for a great adventure.”
Review of Chicago’s 2-hour Segway tour, with Millennium Park, Buckingham Fountain, Museum Campus, guide tips, value, drawbacks, and booking advice.
“It was a great tour, Mike Artur guide was awesome funny and very informative. We would totally recommend it”
See the Art Institute of Chicago’s greatest works with a small-group guide, skip the line, and make sense of the museum in 2.5 hours.
“Balanced tour with an expert guide who appreciated art. Enthusiastically explained the art. Recommend to anyone.”
Explore the Art Institute of Chicago with a private guide, skip-the-line entry, major masterpieces, art stories, and a flexible 2.5-hour route.
“Got a great macro and micro view of the Art Institute with our trusty guide Heath. It was perfect in pace, depth, and tone.”
Cruise the Chicago River at sunset with cocktails, expert architecture commentary, glowing skyscrapers, and century-old bridges.
“A great tour our guide was very informative. A great way to learn and see more about Chicago”
See Chicago’s skyline after sunset from an open-top bus, with live stories, Navy Pier, the Magnificent Mile, Millennium Park, and Museum Campus.
“Excellent way to get a good overview and history of Chicago, especially if this is your first time here. Extremely knowledgeable guide.”
Cruise the Chicago River for 90 minutes, seeing 50-plus skyscrapers with expert narration, free drinks and snacks, and superb city views.
“My husband and I throughly enjoyed the tour! Our guide was very knowledgeable and funny.”
See Chicago’s greatest artworks on a private, flexible Art Institute tour with skip-the-line entry, expert guidance, and all-day museum access.
“Best way to experience the Art Institute of Chicago. So much to see and do, it’s always best to rely on an expert. Joel provided us with all the highlights, including the behind the scenes insights like how the piece was acquired. That allows you to truly experience and appreciate the art. Bonus your ticket is good all day, leave for lunch and come back to experience more at your leisure.”
See Chicago glow at sunset from an open-top bus, with skyline views, a live guide, Museum Campus, Michigan Avenue, and the Bean.
“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.”
See the Art Institute of Chicago before opening with an art expert, small group access, Picasso, Hopper, Cassatt, and more in 150 minutes.
“Mandy was a great tour guide! Very knowledgeable and entertaining! Such a great must see tour!”
Explore Chicago street art on a two-hour walk through Wicker Park, Bucktown, and Logan Square with local artists, history, and live creativity.
“Très belle marche pour découvrir d'autres quartiers de la ville ainsi que l'art de la rue. Merci!”
Explore Chicago with a private local guide, flexible walking routes, landmark views, museum planning, and useful city advice.
“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...”
Walk Chicago’s movie streets from Ferris Bueller to The Dark Knight on a two-hour morning tour with a local guide.
“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 she said OH you booked through Viator, then she emailed me direction where they were actually meeting and hung up. The guide was so stuck on himself we ended up leaving the tour 20 minutes early along with 4 other people. He spent 1 hour and 30 minutes talking about himself and they movies he…”
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