USA · WALKING TOURS IN CHICAGO
This is the shortlist to send a friend: 10 walking tours in Chicago worth the money, each with its price, its traveller verdict and the one thing to know before you commit.
Explore Chicago’s gangster past and ghost stories on a historian-led Loop walk, with stops at the Palmer House, Riverwalk, and Congress Hotel.
“Willis was a great story teller! Easy to find, the only wish is that we were able to stop in more places. Most of the tour is just walking outside not in actual buildings.”
Chicago food tour review covering deep dish, hot dogs, Italian beef, landmarks, guide quality, price, weather, and the bike or kayak bonus.
“It's a fun and delicious way to be introduced to local food and history. We loved hearing about the architecture of famous buildings downtown. All of the food was tasty. Our tour guide was fabulous, fun, and well-informed. Highly recommend this introduction to Chicago!”
Explore Chicago’s gangster past and ghost lore on a lively two-hour South Loop walking tour with historic landmarks and expert storytelling.
“Tanner was really nice Guide. It was a good interesting tour, with much of deap facts.”
Taste deep-dish pizza, hot dogs, Italian beef, and Chicago history while walking the Loop, Riverwalk, Magnificent Mile, and Millennium Park.
“Dave was extremely knowledgeable about Chicago. He gave excellent histories about various places and foods. I appreciated his candor and enthusiasm. The places he took us for food were solid and enjoyable. His ability to help us appreciate our surroundings was a pleasure. At times, his stories were sometimes complicated and difficult to follow - alas that is history sometimes. I think shortening the tour by 30-45 minutes would have made it better.”
Explore Chicago’s secret interiors, grand lobbies, mosaics, domes, and Gilded Age stories on this excellent $35 Loop walking tour.
“Grant was terrific! Very knowledgeable and personable! Saw things we would never have found on our own.”
Review of Chicago’s Chinatown food tour, with generous Chinese tastings, local history, easy walking, price details, and practical booking advice.
“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!”
Explore Chicago’s secret interiors, grand Loop buildings, and architectural stories on a lively two-hour walking tour from Union Station.
“The tour was the highlight of my stay in Chicago. I thoroughly enjoyed the walk and appreciated Annie’s outstanding and extremely knowledgeable commentary. I can recommend this tour wholeheartedly.”
Explore Chicago’s Prohibition past while tasting steak, deep dish pizza, and a classic hot dog on a small-group walking tour.
“Give Ty a big Bonus!! He was awesome! Very informative, knew the subject, added his own twist. Chantal and Jill.”
Explore Chicago’s mob past, haunted hotels, and crime-soaked landmarks on a lively 90-minute walking tour with local guides.
“Be prepared to walk and learn. This was a good tour although I wished we had a few more indoor spots only because it was hard to hear our guide sometimes due to traffic. But the historical stories were really interesting. Alyssa was engaging and knowledgeable. Kept the stories entertaining.”
Explore Chicago’s landmark interiors and skyscraper history on a two-hour architecture walk from the CAC to the Cultural Center.
“Our tour guide John was extremely knowledgeable about the history and architecture of Chicago. We’re very glad we did the tour.”
Every kind of American day out, and the best of each.
