Chicago Walking Tours


CHICAGO · WALKING TOURS

15 Best Chicago Walking Tours

The ones worth booking.

The 15 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.

15 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

“Taka our guide was very knowledgeable about the history of area. The tour was managed time wise and we were all able to know what we were doing and stay together. I learned a lot about the area that I had never knew about before. She spoke so everyone could hear her in the busy…”

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
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Chicago Favorites Ultimate Food and Walking Tour

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Chicago: Gangsters and Ghosts Guided Walking Tour - Chicago Riverwalk and Death Alley: gangster legends on foot
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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
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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

“Our guide did a great job and provided a good mix of cultural information, history and descriptions of the food. Everything was delicious and opened us up to a new part of town!”

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
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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

“Had a great tour with Baylor. We were the only ones on this tour so had all of her knowledge directed at us only. Interesting tour and Baylor was very chatty and friendly!”

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

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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 is a fantastic way to get into the unique history of Chicago’s iconic buildings. Highly recommend for history buffs and architectural aficionados. Our guide Russelll, showed his passion for both the buildings as well as the history of Chicago. This is a “ must do” tour while visiting the Windy City.”

362 reviewsFrom $35.00by Chicago Architecture Center

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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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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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Chicago: Gangsters and Food Tasting Walking Tour - What You’ll Eat on This Tour: Steak, Deep Dish, Tavern-Style Pizza, Chicago Hot Dog
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Chicago: Gangsters and Food Tasting Walking Tour

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Chicago Walking Tour: A Walk Through Time - Starting at the Chicago Architecture Center (and What You’ll Get There)
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Chicago Walking Tour: A Walk Through Time

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14.Chicago Walking Tour: A Walk Through Time

A fast, small-group Chicago architecture walk through landmark buildings in chronological order, starting at the Chicago Architecture Center.

★ 5.0

“We were visiting for two days from London- excellent knowledgeable walking guide. Loved all the quirky facts about various iconic buildings. Added bonus to be able to view the foyer of the Automobile association building.”

181 reviewsFrom $35.00by Chicago Architecture Center

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