Chicago · WALKING TOURS
39 reviewed
Out of 39 walking tours on this site, these 15 are the ones to book. Prices, durations, and the details that matter are all here, so you can pick in five minutes and get back to the fun part.
A 2-hour Loop walk blending prohibition gangland lore with reported hauntings, led by a historian and ending at Congress Plaza.
“Taka was our guide and she was fantastic! The stories were interesting, her directions were clear, she kept the group on time, and she projected her voice and spoke very clearly in a large group on loud city streets. We would definitely recommend this tour!”
Eat classic Chicago favorites on a 3-hour Loop walk with deep-dish, hot dogs, Italian beef, brownie or gelato, popcorn, and a free 2-hour bike or kayak.
“Awesome tour. Great way to hit the touristy spots without it taking up the whole weekend. Greg was 10/10 and wish he could give every tour.”
2-hour South Loop walking tour with a historian guide for gangster stories, ghost legends, and haunted hotel stops at Palmer House and Congress Plaza.
“Our guide Chris was very clear & easy to understand. Excellent as my husband has a hearing issue, and had no problem hearing & communicating with him. He was informative & entertaining.”
Small-group Chicago walking tour with food bites and big architecture stops, plus history stories and a finish near the Loop.
“Dave was very knowledgeable & friendly. Freezing outside but still was able to provide a great experience both inside & outside! I would do this tour again.”
Chicago’s Secret Interiors tour brings you into rarely accessed lobbies and landmarks across the Loop, for $35 and about 2 hours.
“Ethan was great! I was surprised how many people showed up on a rainy Chicago day. Ethan kept our group engaged and safe as we moved around the city going in and out of some very beautiful buildings. He has extensive knowledge of the city and its architecture and history. I highly recommend!”
Chicago Chinatown food and walking tour with 5 generous tastings, dumplings to Portuguese egg tarts, plus landmark stops like Pui Tak Center.
“Great food on this easy walking tour through Chicago’s historic Chinatown. We learned a little about Chinese history, Chicago history, and enjoyed some really great food.”
2-hour Loop walk through secret Chicago interiors: domes, mosaics, and engineering tricks in iconic buildings for $35.
“The tour was very beautiful, interesting, and informative. Our guide Talia was extremely knowledgeable and made the tour very enjoyable. We’ve lived in the area our whole lives and we learned way more than we thought we would have. Great tour, great guide.”
A 2-hour Chicago River North gangster-and-food walk with steakhouse tunnels, deep-dish pizza, and iconic hot dog stops for $79.
“Taka is a great story teller! We throughly enjoyed our time exploring the city with a fun gangster twist and food. Loved the Chicago Hot Dog the best!”
A small-group mob and ghosts walking tour through Chicago’s Loop, from the haunted Congress Plaza to Capone-linked haunts.
“This tour doesn’t match the description. The content was informative but it seemed fragmented. You had to make your own connections to the theme. Left with unanswered questions.”
A 2-hour small-group Chicago architecture walk linking the Loop’s icons to art deco interiors, with CAC admission included for $35.
“Paul was a great tour guide whose passion for the architecture and history of Chicago’s great buildings was evident. The pace was perfect. I didn’t know the Chicago Architecture Foundation existed, but will definitely sign up for another tour when I return.”
Chicago’s Underground Pedway tour: secret passages, architectural interiors, and art meanings, ending near Millennium Park. 2 hours, $35.
“Great walking tour. Learned a lot and Adam was a great guide. Highly recommended.”
Haunted Chicago Booze and Boos is a 2.5-hour Lincoln Park ghost walk with period-costumed guides and classic pubs. Drinks optional.
“Mallory was wonderful descriptive and enthusiastic. She made sure to connect with everyone and left no one behind :)”
2-hour River North walk with three tastings, deep dish, steak and a Chicago hot dog, plus Capone hideouts and a Prohibition tunnel.
“Guide was very knowledgeable, answered any questions. Tour was very entertaining and funny at times . Would definitely recommend this tour which included fabulous tasting food, great stories and value for money . Cracking tour Thank you Alan”
A 2-hour Golden Age walk in Chicago’s Loop with CAC-trained guides. See the Tiffany dome, Macy’s, and the Palmer House for $35.
“Excellent tour with a phenomenal guide. Ron is very knowledgeable and approachable. We highly recommended this tour to anyone interested in architecture.”
A 90-minute Chicago Architecture Center walking tour of iconic buildings in chronological order, with gallery admission and a small-group guide for $35.
“Very knowledgeable guide. Super personable and answered all questions the group had. Did not feel rushed nor did it feel too long and dragged on”
