On Foot · CHICAGO WALKING TOURS
Every trip has one free morning too few. These 13 walking tours in Chicago earn the slot, priced and timed so you can decide in minutes and get back to packing.
Explore Chicago’s Loop through true gangster tales, ghost stories, Al Capone sites, and haunted hotels on a lively two-hour walking tour.
“Taka was so incredibly knowledgeable. She taught me so many things about Chicago. I had no idea and I’ve been living in Chicago. Almost my whole life. The way that she tells a story was so intriguing and engaging. She really made everyone in our group feel included Read more”
Taste deep dish, hot dogs, Italian beef, brownies and popcorn while exploring Chicago landmarks on a relaxed 3-hour walking tour.
“Fun, funny, and informative guide (Gabe)!! Learned a lot about the food, history, and architecture of Chicago! Nice variety of delicious food!”
Explore Chicago’s gangster past and ghostly legends on a two-hour South Loop walking tour with historic landmarks and lively storytelling.
“It was a fun and interesting tour. Baylor was a great and entertaining guide.”
Taste Chicago classics, from deep dish to Italian beef, while exploring Loop architecture on a three-hour small-group walking tour.
“Our guide Danny was excellent. He had so much information to share with the group about Chicago in general, several famous buildings, the restaurants we visited and the food we ate. At the beginning, he had all of our names memorized and kept good track of us throughout the tour. The food was a great representation of famous Chicago treats and I learned so much from him.”
Explore Chicago’s secret interiors, domes, mosaics, and engineering feats on a lively two-hour Loop walking tour.
“We visited places on this tour that we would never have known about or seen on our own. Talia did a wonderful job and was very knowledgeable.”
Explore Chicago’s Pedway, secret passages, public art, and hidden interiors on a practical two-hour walking tour for $35.
“A very interesting tour, it would be very difficult to find your way on the Pedway without a guide and Heath was a fun tour guide”
Taste steak, hot dogs and two Chicago pizzas while exploring Capone-era hideouts and River North mob stories on this lively two-hour walk.
“it was brilliant, very enjoyable. Baylor was a great guide!”
Explore Chicago’s Golden Age architecture on a two-hour CAC walking tour featuring Tiffany glass, grand hotels, department stores, and expert guides.
“Learned a lot about the history of Chicago and its buildings.”
Explore Chicago’s Prohibition bars by foot or bus, with sharp stories, historic venues, drink tips, and practical advice for a $47 tour.
“Wonderful tour! Jonathan Knotek was our tour guide. He reached out the day before and advised the details on where to meet. He was extremely knowledgeable, witty & truly made the trip worth every penny. I was a little surprised to be picked up in a school bus but the driver was really sweet and added a bit of humor to the trip. The stops had amazing drinks & the food at Lucky’s was some of the best Italian food we ever had. Would highly recommend!”
Taste five Chicago classics, explore downtown with a local guide, and add a free bike or kayak rental to your $84 food tour.
“Fantastic tour! Excellent history whilst walking around Chicago. Food was awesome and so much of it!”
Taste five Chinese specialties, explore Chicago Chinatown landmarks, and learn the neighborhood’s stories on this generous three-hour food tour.
“Jeff did an amazing job with the food, culture, and history of Chinatown. Ate some of the best food ever and learned a lot! I traveled by myself and he made me feel welcomed and everyone in my group made me feel like part of their family! I would recommend this tour to anyone looking for an inside route to great food and learning about Chinese history.”
Taste Chicago hot dogs, deep-dish pizza, and Italian beef while exploring Loop history on a small-group food walk.
“Delicious food, we were shown places we would otherwise never have found ourselves. The guide was very friendly, enthusiastic and informative on many topics, not just about food 🙂”
Explore Chicago’s landmark architecture on a 90-minute CAC walking tour, with expert guides, city stories, and exhibit admission included.
“Spectacular and very educational tour. Our guide was fantastic!!”
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