Chicago Walking Tours


CHICAGO · WALKING TOURS

12 Best Chicago Walking Tours

The ones worth booking.

The 12 chicago walking tours travellers book the most. We walk you through what each one covers on the ground, who guides it and what it costs, so you can pick the right one before you lace up.

12 Best Chicago Walking Tours

Chicago: Gangsters and Ghosts Walking Tour - Price and time: is $52 a good value for two hours?
Chicago, Chicago Walking Tours, Ghost & Dark History Walks, Tour Reviews, Tours, True Crime & Mafia Walks, Walking Tours

Chicago: Gangsters and Ghosts Walking Tour

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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.

Most Popular★ 5.0

“It was a very cold, windy Chicago night but the tour guide braved it out so we did too--and so glad we did! It was interesting listening to all of the stories about Chicago while wallking around the streets at night. We really enjoyed the tour but will never swim in the water in and…”

7,155 reviewsFrom $52by Chicago Tours

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Chicago Favorites Ultimate Food and Walking Tour - The deep-dish kickoff: where the cheesy legend starts
Chicago, Chicago Walking Tours, Food, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago Favorites Ultimate Food and Walking Tour

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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

“AJ did an amazing job not only bringing us to some amazing food but also telling us about the history of the city as we went, we learned so much we otherwise may have never learned!”

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 - Chicago Riverwalk and Death Alley: gangster legends on foot
Chicago, Chicago Walking Tours, Ghost & Dark History Walks, Guided, Tour Reviews, Tours, True Crime & Mafia Walks, Walking Tours

Chicago: Gangsters and Ghosts Guided Walking Tour

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Chicago's Secret Interiors Architectural Walking Tour - The Loop start: from art deco to the money-canyon feeling
Chicago, Chicago Walking Tours, Hidden Gems & Local Walks, Tour Reviews, Tours, Walking Tours

Chicago’s Secret Interiors Architectural Walking Tour

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Chicago's Chinatown Food and Walking Tour - Price, Timing, and What Makes It Feel Like Value
Chicago, Chicago Walking Tours, Food, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago’s Chinatown Food and Walking Tour

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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

“Chicago is a beautiful city and it’s with filled with so much rich history and I would recommend going to this tour.”

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

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Chicago Gangster and Food Walking Tour - River North Stop 1: Harry Caray’s Steakhouse and the Tunnel Story
Chicago, Chicago Walking Tours, Food, Food & Drink, Tour Reviews, Tours, True Crime & Mafia Walks, Walking Tours

Chicago Gangster and Food Walking Tour

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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 - Route reality: pickup, ending point, and walking pace
Chicago, Chicago Walking Tours, Ghost & Dark History Walks, Tour Reviews, Tours, Walking Tours

Chicago Mobs and Haunts Walking Tour

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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

“Unfortunately was not what I expected. Lots of talking & walking. No actual indoor sight visits just from afar. Guide spoke too fast.”

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

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Chicago Walking Tour: Historic Treasures of Chicago - Starting at 111 E Wacker: The Chicago Architecture Center Galleries Setup
Chicago, Chicago Walking Tours, Historical Tours, Tour Reviews, Tours, Walking Tours

Chicago Walking Tour: Historic Treasures of Chicago

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Chicago: Underground Pedway & Downtown Secrets Walking Tour - Starting at 120 N LaSalle and getting your bearings fast
Chicago, Chicago Walking Tours, Hidden Gems & Local Walks, Tour Reviews, Tours, Underground & Vaults Walks, Walking Tours

Chicago: Underground Pedway & Downtown Secrets Walking Tour

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Haunted Chicago Booze and Boos Ghost Walking Tour - Lincoln Park’s spooky route: John Dillinger and the alley beside the theater
Chicago, Chicago Walking Tours, Ghost & Dark History Walks, Tour Reviews, Tours, Walking Tours

Haunted Chicago Booze and Boos Ghost Walking Tour

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Chicago: Gangsters and Food Tasting Walking Tour - What You’ll Eat on This Tour: Steak, Deep Dish, Tavern-Style Pizza, Chicago Hot Dog
Chicago, Chicago Walking Tours, Food, Food & Drink, Tour Reviews, Tours, True Crime & Mafia Walks, Walking Tours

Chicago: Gangsters and Food Tasting Walking Tour

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