Chicago · GUIDED
This is the shortlist to send a friend: 15 guided tours worth the money, each with its price, its traveller verdict and the one thing to know before you commit.
A 90-minute Chicago River architecture cruise with expert storytelling, indoor warmth or open-air decks, and iconic skyline stops plus a cash bar.
“Our guide was first class with his knowledge and interpretation of the Chicago architecture. Combine that with the history and the ability to weave amusing anecdotes, and excellent diction made this a trip out of the ordinary.”
Chicago South Loop gangsters and ghosts guided walk with a historian, inside hotel stops, Riverwalk and Death Alley stories, 2 hours.
“Bailor was our guide and she’s the best! Super interesting and fun. We were happy to learn new things of Chicago.”
A spooky 1.5-hour torture museum in Chicago with an audio guide and a ghost-hunting app, plus plenty of photo-ready, interactive displays.
“Very enlightening museum with a well done audio tour. We are very fortunate to be in more civilized times!”
2-hour small-group Segway tour of Chicago from 2 E 8th St. Learn to ride and glide past Millennium Park, Buckingham Fountain, and more.
“The great stories were entertaining and the old airport nature preserve was a beautiful surprise! Thank you Mike!”
Skip-the-line Art Institute of Chicago guided tour with a small group, 2.5 hours of key artworks, and an expert-led highlights circuit.
“Great way to get a highlights tour of the Art Institute. Bernie was a wealth of information and a great guide to the museum. If you don't have a lot of time in Chicago this is a wonderful introduction to the attraction”
A private, skip-the-line guided tour of the Art Institute of Chicago, covering major works and stories in 2.5 hours.
“Samantha was knowledgeable, quite insightful, and animated just enough to keep our attention and desire to learn focused.”
Sunset cocktail cruise on the Chicago River with award-winning docents. See 50+ buildings, 100-year bridges, and city lights in 90 minutes.
“I had a great experience, the staff was friendly and the tour guide was very informative, I learned a lot of interesting facts about the buildings and had a good time sightseeing with a drink in my hand. 5 out of 5 stars”
See Chicago’s skyline lit up on an open-top sunset bus with a live guide in English or Spanish, plus great photo stops.
“Excellent way to see Chicago…the guide was humorous, knowledgeable and extremely informative. It was definitely a great experience.”
90 minutes on an open-air Chicago Riverboat with docent narration, free coffee and snacks, and views of 50+ major buildings.
“Jim packed a lot of information into 90 mins — we learnt a lot! The views were spectacular and many Chicagoans have confirmed since that its the best way to see the city. Complementary water, lemonade and coffee was a welcome touch.”
Private 2-hour Art Institute of Chicago tour with skip-the-line entry, expert guide, and major works, plus time to explore more after.
“Marlin was an excellent guide with flexibility for our interests guiding us through the art museum tour with authenticity, highlights, and fun.”
Ride an open-top double-decker on Chicago’s sunset skyline loop, with a live guide and big views from Museum Campus to Millennium Park.
“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 with an art expert at Chicago's Art Institute, early entry, small groups, and a 150-minute highlight tour. $90.
“Joe was knowledgeable and very enthusiastic. Great tour. Good with kids.”
2-hour guided street art tour in Chicago, walking Wicker Park, Bucktown, and Logan Square with mural stories and live artists.
“Savoir, explication, intelligence, pointure dans son sujet…. Très bon ! Je recommande!!”
A private, customizable Chicago walking tour with a local guide, tailored sights, optional museum time, and practical insider tips in your language.
“Service sublime notre guide Bart nous a bien expliqué l’histoire de Chicago le tout dans un français parfait :) une visite à faire on aurait du prendre davantage de temps que 2h je recommande vivement cette visite en français de l’histoire de Chicago”
Walk Chicago’s top TV and movie filming stops with a guide, hitting Willis Tower, Ocean’s 11, The Dark Knight, and more in 2 hours.
“It was a great tour and are tour guide was awsome he talk a lot on and about the TV and movie history”
Every kind of day out in the city, and the best of each.
