Chicago
I picked the walking tours that do more than loop Millennium Park. The good guides cover the L tracks, the old banking halls, and the Pedway tunnels under the Loop. Two hours is the standard length, and winter routes simply move underground.
Bask in the mysterious allure of Chicago's past on the 'Gangsters and Ghosts Guided Walking Tour,' where secrets linger and history whispers...
Most Popular★ 4.7“Alan was great, enthusiastic and informative guide. Was well worth the money, great way to explore Chicago and would highly recommend”
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1,697 reviews2 hoursFrom $36by Chicago Gangsters and Ghosts Tours
Discover the hidden gems of Chicago's Loop with our captivating architecture walking tour. Immerse yourself in stunning interiors that will leave you breathless!
★ 5.0“Very informative for everyone. Opened doors to buildings that I would have assumed were not open to the public for casual visiting.”
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1,489 reviews2 hours (approx.)From $35.00by Inside Chicago Walking Tours
Discover the best of Chicago in just one day! Immerse yourself in its vibrant food scene, rich history, and stunning architecture on an unforgettable walking tour.
★ 5.0“Excellent Tour guide. David was so knowledgeable, patient and helpful. I was on a rolator David knew exactly where the elevators were located. By preparing for the locations, it made everyone comfortable.”
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1,153 reviews4 hours 30 minutes (approx.)From $100.95by Intrepid Urban Adventures - USA
With a maximum group size of 15, the Chicagos Secret Interiors Architectural Walking Tour unveils the city's hidden gems, showcasing intricate domes and stunning gardens.
★ 5.0“Avery gave us a lot of good info on the tour and kept the group moving along. It did not overlap at all with a boat tour. We were glad we did this.”
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635 reviewsFrom $35by Chicago River Boat Architecture Tours
Discover the vibrant flavors of Chicago's Chinatown on a mouthwatering food and walking tour. Indulge in authentic cuisine and immerse yourself in the rich cultural heritage.
★ 5.0“Lillian, our guide was very knowledgable and made the tour fun. The food was plentiful and delicious. Would recommend this tour.”
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600 reviews3 hours (approx.)From $79.99by Bobby's Bike Hike - Chicago
Delve into Chicago's hidden architectural gems on the Secret Interiors Architecture Walking Tour, where mysteries and untold stories beckon to be uncovered.
★ 4.9“Our guide Grant was fantastic! My friend and I took the tour on a cold February day and enjoyed every minute of it. Grant is very personable and knowledgeable. The architectural details we saw were stunning. Definitely recommend this tour!”
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498 reviews2 hoursFrom $35by Chicago River Boat Architecture Tours
Discover the thrilling underworld of Chicago's gangsters as you indulge in mouthwatering local cuisine. Join our walking tour today and experience the best of both worlds!
★ 5.0“Loved learning the history of the Irish North and Italian South gangs and the clever ways they stuck it to each other. Pizza was phenomenal, and Harry Carrys basement was so interesting with the tunnels!”
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471 reviewsFrom $79by Chicago Tours
Discover the hidden wonders of Chicago's Underground Pedway and uncover the secrets of the Loop on an unforgettable architecture walking tour. Explore now!
★ 5.0“Great tour with knowledgeable guide! So interesting to learn about the pedway in Chicago! Been to the city multiple times and had no idea there were underground walkways!”
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388 reviews2 hours (approx.)From $35.00by Inside Chicago Walking Tours
Blending Chicago's dark history and eerie legends, the Chicago Mobs and Haunts Walking Tour promises an unforgettable exploration for thrill-seekers, leaving visitors intrigued to learn more.
★ 4.5“It’s just a great tour, takes you around the city hotspots of where things happened in history, the tour guide was very knowledgable about the city”
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383 reviews1 hour 30 minutes to 2 hours (approx.)From $34.00by ExperienceFirst
Discover the hidden gems of Chicago's fascinating history on a captivating walking tour. Uncover the city's historic treasures like never before. Join us today!
★ 5.0“Very informative and guide was very friendly and knowledgeable! Guide accommodating to our needs. Beautiful way to see some of the city.”
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362 reviewsFrom $35.00by Chicago Architecture Center
Step into the mysterious world beneath Chicago's streets on the 'Chicago: Underground Pedway & Downtown Secrets Walking Tour' and prepare to be spellbound by hidden tales waiting to be revealed.
★ 4.7“Great!Kayley was amazing and give us great spots of Chicago”
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268 reviews2 hoursFrom $35by Inside Chicago Walking Tours
Discover the chilling secrets of Chicago's haunted past on our Ghost and Pub Walking Tour. Prepare for spine-tingling encounters and supernatural stories!
★ 5.0“It was such a fun experience!!! Lara was a fantastic guide, very knowledgeable, and friendly! She took us to some really cool bars and told us some great ghost stories! It’s also a great way to check out the city and meet new people! I…”
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266 reviews2 hours 30 minutes (approx.)From $35.87by Nightly Spirits
Yearn for an adventure where the echoes of Chicago's underworld meet the flavors of its culinary scene, igniting a journey filled with intrigue and indulgence.
★ 4.6“Our guide Alan was fantastique and very interesting and funny , the good was very good . Thank you”
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228 reviews2 hoursFrom $81by Chicago Gangsters and Ghosts Tours
Navigate through Chicago's architectural wonders on the 'Treasures of the Golden Age Walking Tour' to uncover hidden stories that will ignite your curiosity.
★ 4.8“The buildings we saw and what we learned about them. The docent was engaging and knowledgeable.”
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206 reviews2 hoursFrom $35by Chicago Architecture Center
Explore the rich history of Chicago on an enchanting walking tour. Discover hidden gems, iconic landmarks, and fascinating stories. Uncover the city's past, step by step.
★ 5.0“My husband and I had a wonderful time at this tour. Our guide was very knowledgeable and fun. I definitely recommend.”
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181 reviewsFrom $35.00by Chicago Architecture Center
I plan Chicago around the water: architecture from the river, skyline from the lake, and deep dish to recover afterward.