Chicago · WALKING TOURS
91 tours
Chicago is a walking city for about seven months a year, and a good guide makes the other five worth the coat. These walks cover the Loop lobbies, the gangster addresses, the food counters and the neighbourhood streets, with distances, durations and prices.
Chicago Loop gangster tales and ghost stories on a 2-hour historian walk. Millennium Park, Palmer House, Riverwalk, and Capone legends.
“Very exotic experience, another good way to know about Chicago history beside just regular tourist spots”
A 3-hour food and walking loop through Chicago classics, Millennium Park sights, and downtown landmarks, plus a free bike or kayak bonus.
“We were combined with the Holiday food tour to make a group of 14 (Christmas Eve). Our guide, Fran, was personable and knowledgeable, and kept the group moving. My husband and I enjoyed the food and the stories--it was a great introduction to the city of Chicago.”
A 2-hour Chicago South Loop walk mixing Al Capone era stories and ghost legends, with stops at iconic landmarks and hotel interiors.
“Sophia was a delight! This was my favorite tour of this trip. So much knowledge and lore crammed into 2 hours. A must for true crime, history, and ghost story fans.”
A small-group Chicago walking tour packing deep-dish, hot dog and Italian beef with Pedway, river views, and top architecture sights.
“The tour guide was very knowledgeable, super friendly, with a great Humor, making even an international guest feeling very comfortable. The tour was very interesting and I learned quite a lot about Chicago and the Chicago food.”
A 2-hour Chicago Loop walk focused on rare interior access, big-name landmarks, and hidden craftsmanship, with a small guided group.
“Ethan our guide did an incredible job. Chicago is such a beautiful city with such a rich architectural history. Was a great way to see things you had no idea were even there.”
A 3-hour Chicago Chinatown food walk with dim sum, hand-pulled noodles, Sichuan heat, Xi’an lamb, and Portuguese egg tarts.
“Jeff was a fantastic guide! The food was so good, the history and side stories were great, lovely group of your attendees, and overall just a wonderful time. Would definitely recommend and would absolutely take another tour with Jeff and/or the tour company!”
Discover Chicago’s secret interiors on a 2-hour Loop walk, seeing domes, mosaics, and engineering stories for $35 a person.
“Talia was an amazing representation of the tour company. They did stellar and I would book again if I saw more buildings. Even in the winter it was well worth the cold.”
Prohibition-era gangster stories plus Chicago classics in a small-group 2-hour food walk for $79, from River North to the Gold Coast.
“We booked this tour for a client and they absolutely loved it! They could not say enough good things about their tour guide, Avery. He was so knowledgeable about the city's history, the architecture, and they said that he was the reason they had such a great tiRead more”
A mob and ghost walking tour in Chicago’s Loop, featuring haunted hotel tales, Capone’s hangouts, and spooky alleys, guided for $34.
“This was a very informative tour led by Alyssa, who is very knowledgeable about all things Chicago!!”
Walk Chicago’s Loop with a certified docent, see iconic landmarks up close, and get CAC gallery admission plus key interior stops.
“Guide was great. Knowledgable and humorous. Happy for questions and open to question. Truly interesting interiors.”
Walk Chicago’s Pedway to secret stained-glass corridors and underground pools, end near Millennium Park, and learn a transit shortcut.
“Colleen was an excellent guide and very friendly. She not only shared her knowledge on the tour, she also gave us tips for where to eat, where to go and what to do in out time in Chicago.”
A 2.5-hour Haunted Chicago Booze and Boos ghost walking tour in Lincoln Park with bar stops, period-dressed guides, and spooky city stories.
“We had a wonderful time with Katie on the tour! She was so knowledgeable on the history of the area and took us to amazing bars! I would absolutely recommend this tour and will be taking it in the other locations as well.”
Chicago gangs and iconic bites on a 2-hour River North walk with three tastings, Capone hideouts, and deep dish pizza.
“The guide Payton was really nice and we had a lovely tour with her. For food there was some steak, a slice of Deep dish pizza and then also chicago hotdog. We were really full afterwards. So there was also enough to eat. And we enjoyed the stories about the gangsters.”
A 2-hour Chicago Loop walk through Golden Age architecture, with Chicago Architecture Center exhibits plus stops like the Tiffany dome and Palmer House.
“Excellent tour with entertaining stories by the guide next to being very informative.”
A fast, small-group Chicago Architecture Center walking tour tracing iconic buildings in time order, with galleries admission included for $35.
“Perfect tour. Well thought out. Loved the history woven in. So interesting that I took notes! And our docent was so approachable and entertained numerous questions from numerous attendees.”
