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15 Best Walking Tours In Chicago

The best of Chicago.

The 15 best walking tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.

15 Best Walking Tours In Chicago

Chicago: Gangsters and Ghosts Walking Tour - Meeting point and timing: how to start smoothly
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Chicago: Gangsters and Ghosts Walking Tour

1.Chicago: Gangsters and Ghosts Walking Tour

A historian-led Chicago Loop walk mixing Prohibition-era mob stories and reported ghost sites, with optional minibus upgrade for $52.

Most Popular 5.0

“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”

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Chicago Favorites Ultimate Food and Walking Tour - Route and pacing: 1.25–1.5 miles, Pedway in winter
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Chicago Favorites Ultimate Food and Walking Tour

Chicago: Gangsters and Ghosts Guided Walking Tour - The Chicago Riverwalk and Death Alley: spooky stories in a place with real weight
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Chicago: Gangsters and Ghosts Guided Walking Tour

3.Chicago: Gangsters and Ghosts Guided Walking Tour

Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.

4.7

“This tour was good cool information about the city's history, our tour guide Adam was very funny and attentive throughout would definitely recommend 😁”

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Chicago in a Day: Food, History & Architecture Walking Tour - The Chicago Pedway: see downtown Chicago the way locals do
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Chicago in a Day: Food, History & Architecture Walking Tour

4.Chicago in a Day: Food, History & Architecture Walking Tour

Deep-dish, hot dog, Italian beef and Chicago skyline stories on a small-group 4.5-hour walk with the Pedway and The Bean.

5.0

“John, the tour guide, deserves a 7 but I can't give this tour a 5 for a few reasons that will go overlooked if I just give it a 5. There has to be a few changes. I'm normally generous with my ranking but that doesn't usually inspire change. What should be known and considered…”

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Chicago's Secret Interiors Architectural Walking Tour - Stop 1–3: The Loop’s money core, Financial Canyon, and Union Station
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Chicago’s Secret Interiors Architectural Walking Tour

Chicago's Chinatown Food and Walking Tour - Phoenix Restaurant: The Dumpling Start That Sets The Tone
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Chicago’s Chinatown Food and Walking Tour

6.Chicago’s Chinatown Food and Walking Tour

Taste regional Chinese dumplings, noodles, Sichuan heat, and Portuguese egg tarts on a 3-hour Chinatown walk with landmark stops.

5.0

“This is a great tour of ChinaTown in Chicago. The food was delicious and we were stuffed! The tour guide Greg, was excellent. Plenty of breaks during the tour. Highly recommend this tour!!!!”

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Chicago: Secret Interiors Architecture Walking Tour - Union Station Meeting Point: Where Your Route Really Starts
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Chicago: Secret Interiors Architecture Walking Tour

7.Chicago: Secret Interiors Architecture Walking Tour

Chicago Loop secret interiors tour: $35, 2 hours from Union Station to iconic landmarks. Learn how light and structure shaped the city.

4.9

“Great tour, saw amazing interiors that we would not otherwise have known about. Annie was the perfect guide - friendly, knowledgeable and had great recommendations for food & drink in Chicago. Highly recommend 😊”

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Chicago Gangster and Food Walking Tour - River North at Harry Caray’s: steak plus the basement tunnel story
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Chicago Gangster and Food Walking Tour

8.Chicago Gangster and Food Walking Tour

Prohibition-era gangster stories meet Chicago food in 2 hours. Small-group walk with Harry Caray steak, deep-dish pizza, and dawgs.

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!”

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Chicago Mobs and Haunts Walking Tour - Before You Go: Timing, Weather, and Hearing the Stories
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Chicago Mobs and Haunts Walking Tour

9.Chicago Mobs and Haunts Walking Tour

Chicago Mobs and Haunts walking tour mixes Capone hangouts, haunted hotels, and ghost stories in the Loop for $34 in under 2 hours.

4.5

“This tour doesn’t match the description. The content was informative but it seemed fragmented. You had to make your own connections to the theme. Left with unanswered questions.”

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Chicago Walking Tour: Historic Treasures of Chicago - Start strong: Chicago Architecture Center galleries and a docent intro
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Chicago Walking Tour: Historic Treasures of Chicago

10.Chicago Walking Tour: Historic Treasures of Chicago

Historic treasures of Chicago on a small-group 2-hour walk: CAC galleries, Wrigley Building views, Palmer House lobby, Cultural Center.

5.0

“Rainy day so my son and I debated going. Glad we participated as the docent Beth was excellent. Knowledgeable, interesting and responsive to our questions. Fascinating blend of design and Chicago history.”

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Chicago: Underground Pedway & Downtown Secrets Walking Tour - Part One: How the Chicago Pedway Works Under Full Blocks
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Chicago: Underground Pedway & Downtown Secrets Walking Tour

Haunted Chicago Booze and Boos Ghost Walking Tour - Lincoln Park in motion: Dillinger lore and spooky corners along the route
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Haunted Chicago Booze and Boos Ghost Walking Tour

Chicago: Gangsters and Food Tasting Walking Tour - Price and Time: What You’re Really Paying For
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Chicago: Gangsters and Food Tasting Walking Tour

13.Chicago: Gangsters and Food Tasting Walking Tour

Chicago gangster food walk with Capone-style tunnel access, River North stories, and tastings of deep dish pizza, steak, and a Chicago hot dog.

4.6

“Alan our guide was excellent! Great stories, knew the city, knew the history and was just alot of fun. Very good at his job. Highly recommend this tour with Alan.”

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Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Marquette Building: skyscraper swagger, inside-and-out
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Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

14.Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

A small-group Chicago walk mixing big-name art, iconic skyscrapers, and humor, ending at the Chicago Cultural Center.

5.0

“Colin took us to beautiful architectural sites that even long time Chicagoans likely never admire. He was informative, articulate and moved at a good pace for our group of 8. I highly recommend this tour to even the most seasoned Chicago residents!!”

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Chicago: Treasures of the Golden Age Walking Tour - Meeting at Chicago Architecture Center and getting extra value from the exhibits
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Chicago: Treasures of the Golden Age Walking Tour

15.Chicago: Treasures of the Golden Age Walking Tour

Golden Age Chicago Loop architecture walk with a CAC-certified guide, Tiffany dome, Macy’s on State, and a glimpse inside Palmer House.

4.8

“Weather was perfect, so …. 😀 Guide John was excellent, informative. Love the Chicago Architecture Inst-guided toured - very interesting and professionally done.”

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More Walking Tours In Chicago

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