12 Best Chicago Walking Tours

Chicago, Chicago Walking Tours, Ghost & Dark History Walks, Tour Reviews, Tours, True Crime & Mafia Walks, Walking Tours

Chicago: Gangsters and Ghosts Walking Tour

/ June 16, 2026

1.Chicago: Gangsters and Ghosts Walking Tour

Prohibition-era gangster tales and ghost stories across Chicago’s Loop, haunted hotels, and Millennium Park. Historian guide.

Chicago Favorites Ultimate Food and Walking Tour

/ June 16, 2026

2.Chicago Favorites Ultimate Food and Walking Tour

Taste classic Chicago staples on a 3-hour Loop walk with generous bites, Millennium Park sights, and a free bike or kayak add-on.

★ 5.0

“It wss a great experience. MJ knows his stuff. The food is good at nice places. It was better than expected.”

1,962 reviews3 hours (approx.)From $84.99by Bobby's Bike, Hike & Food Tours - Chicago

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Chicago: Gangsters and Ghosts Guided Walking Tour

/ June 16, 2026

3.Chicago: Gangsters and Ghosts Guided Walking Tour

Historian-led Chicago South Loop walk mixes gangster legend and ghost lore, with hotel interiors, Death Alley, and the Congress Hotel.

★ 4.7

1,697 reviews2 hoursFrom $36by Empire Tours & Productions (Chicago Gangsters and Ghosts Tours)

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Chicago’s Secret Interiors Architectural Walking Tour

/ July 28, 2026

4.Chicago’s Secret Interiors Architectural Walking Tour

Chicago’s Secret Interiors walking tour with rare access to landmark lobbies, mosaics, and gardens for about two hours.

★ 5.0

“Grant was an extremely warm, knowledgeable and organized tour guide. He seamlessly lead a group of 15-20 of us from building to building. It was a very cold day but we do spend a good amount of time indoors so the weather felt really manageable. It was really cool tRead more”

635 reviewsFrom $35by Chicago River Boat Architecture Tours

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Chicago’s Chinatown Food and Walking Tour

/ July 30, 2026

5.Chicago’s Chinatown Food and Walking Tour

Chicago Chinatown food and walking tour with dim sum dumplings, hand-pulled noodles, Sichuan heat, Xi’an lamb, and Portuguese egg tart.

★ 5.0

“Great tour experience with AJ! Learned amazing history about the neighborhood and ate some soulful Chinese food.”

600 reviews3 hours (approx.)From $79.99by Bobby's Bike, Hike & Food Tours - Chicago

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Chicago: Secret Interiors Architecture Walking Tour

/ August 5, 2026

6.Chicago: Secret Interiors Architecture Walking Tour

A 2-hour Loop walk inside Chicago landmarks, spotting secret interiors, design clues, and engineering tricks for $35.

★ 4.9

498 reviews2 hoursFrom $35by Empire Tours & Productions (Chicago River Boat Architecture Tours)

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Chicago Gangster and Food Walking Tour

/ August 7, 2026

7.Chicago Gangster and Food Walking Tour

Gangster tales meet lunch in Chicago. River North tunnels, deep-dish pizza, Chicago Dawg, and Holy Name gunfire history on a 2-hour walk.

★ 5.0

“My husband booked a last minute tour and our guide Avery was great! He was so knowledgeable about the history of Chicago and we learned so much. It was so nice meeting new people and exploring a little! I highly reccomend this tour. The food we sampled was also excellent!”

471 reviewsFrom $79by Chicago Tours

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Chicago Mobs and Haunts Walking Tour

/ August 16, 2026

8.Chicago Mobs and Haunts Walking Tour

A 1.5-2 hour Chicago walking tour mixing mob hangouts and haunted alleys, with Loop under the L, Congress Plaza, and the 226 Club.

★ 4.5

“Mitch was a terrific tour guide. Great insider stories about ghosts...and more importantly...the mob within the historical context of Chicago. Learned much and also got to see some of the more interesting architectural and historic Chicago landmarks.”

383 reviews1 hour 30 minutes to 2 hours (approx.)From $34.00by ExperienceFirst

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Chicago Walking Tour: Historic Treasures of Chicago

/ August 19, 2026

9.Chicago Walking Tour: Historic Treasures of Chicago

A 2-hour small-group architecture walk in Chicago’s Loop, with CAC galleries included and highlights like Palmer House and the Cultural Center.

★ 5.0

“This tour was very informative and very interesting. Bob P. did a great job is our tour leader. I would definitely recommend the tour.”

362 reviewsFrom $35.00by Chicago Architecture Center

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Chicago: Underground Pedway & Downtown Secrets Walking Tour

/ September 4, 2026

10.Chicago: Underground Pedway & Downtown Secrets Walking Tour

Explore Chicago’s underground Pedway by guided secret passages, stained glass interiors, and downtown art clues for $35 in 2 hours.

★ 4.7

268 reviews2 hoursFrom $35by Inside Chicago Walking Tours

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Haunted Chicago Booze and Boos Ghost Walking Tour

/ September 5, 2026

11.Haunted Chicago Booze and Boos Ghost Walking Tour

Haunted Chicago Booze and Boos pub crawl in Lincoln Park with costumed guides, three bars, Oz Park stops, and spooky stories.

★ 5.0

“The experience was so much fun! And our tour guide Katie was amazing! We also got to learn about so many cool bars, we even went back to one after the tour was over.”

266 reviews2 hours 30 minutes (approx.)From $35.87by Nightly Spirits

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