15 Best Walking Tours In Chicago

Chicago, Gangster & Crime Tours, Ghost & Haunted Tours, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Ghosts Walking Tour

/ June 4, 2026

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.

Chicago Favorites Ultimate Food and Walking Tour

/ June 4, 2026

2.Chicago Favorites Ultimate Food and Walking Tour

Taste Chicago classics on a 3-hour walking tour with deep-dish, Italian beef, hot dogs, brownie and popcorn plus a free 2-hour bike or kayak.

★ 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, Gangster & Crime Tours, Ghost & Haunted Tours, Guided, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Ghosts Guided Walking Tour

/ June 4, 2026

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 😁”

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

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Architecture Walking Tours, Chicago, Food, Food & Drink, Historical Tours, Sightseeing & City Tours, Tour Reviews, Tours, Walking Tours

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

/ June 4, 2026

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…”

1,153 reviews4 hours 30 minutes (approx.)From $100.95by Intrepid Urban Adventures - USA

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Architecture Walking Tours, Chicago, Tour Reviews, Tours, Walking Tours

Chicago’s Secret Interiors Architectural Walking Tour

/ June 4, 2026

5.Chicago’s Secret Interiors Architectural Walking Tour

Chicago Loop interiors and skyline views on a 2-hour walking tour with rare access to lobbies, domes, mosaics, and iconic landmarks.

★ 5.0

“Well put together tour, not too long, knowledgeable guide:) interesting places. Definitely would recommend!”

635 reviewsFrom $35by Chicago River Boat Architecture Tours

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Chicago, Chinatown Tours, Food, Food & Culinary Tours, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago’s Chinatown Food and Walking Tour

/ June 4, 2026

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!!!!”

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

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Architecture Walking Tours, Chicago, Tour Reviews, Tours, Walking Tours

Chicago: Secret Interiors Architecture Walking Tour

/ June 4, 2026

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 😊”

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

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Chicago, Food, Food & Drink, Gangster & Crime Tours, Tour Reviews, Tours, Walking Tours

Chicago Gangster and Food Walking Tour

/ June 4, 2026

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!”

471 reviewsFrom $79by Chicago Tours

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Chicago, Gangster & Crime Tours, Ghost & Haunted Tours, Tour Reviews, Tours, Walking Tours

Chicago Mobs and Haunts Walking Tour

/ June 4, 2026

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.”

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

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Chicago, Historical Tours, Tour Reviews, Tours, Walking Tours

Chicago Walking Tour: Historic Treasures of Chicago

/ June 4, 2026

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.”

362 reviewsFrom $35.00by Chicago Architecture Center

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Architecture Walking Tours, Chicago, Tour Reviews, Tours, Walking Tours

Chicago: Underground Pedway & Downtown Secrets Walking Tour

/ June 4, 2026

11.Chicago: Underground Pedway & Downtown Secrets Walking Tour

Explore Chicago’s Underground *Pedway* with an expert guide, secret interiors, and art meaning clues near Millennium Park.

★ 4.7

“The guide was very knowledgeable about the history of Chicago , the buildings and the pedway.”

268 reviews2 hoursFrom $35by Inside Chicago Walking Tours

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Chicago, Ghost & Haunted Tours, Prohibition & Speakeasy Tours, Tour Reviews, Tours, Walking Tours

Haunted Chicago Booze and Boos Ghost Walking Tour

/ June 4, 2026

12.Haunted Chicago Booze and Boos Ghost Walking Tour

Booze and Boos takes you through Lincoln Park pubs and ghost lore in about 2.5 hours with a costumed guide and drink stops.

★ 5.0

“Mallory was wonderful descriptive and enthusiastic. She made sure to connect with everyone and left no one behind :)”

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

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Chicago, Food, Food & Culinary Tours, Food & Drink, Gangster & Crime Tours, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Food Tasting Walking Tour

/ June 4, 2026

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.”

228 reviews2 hoursFrom $81by Empire Tours & Productions (Chicago Gangsters and Ghosts Tours)

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Chicago, Historical Tours, Tour Reviews, Tours, Walking Tours

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

/ June 4, 2026

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!!”

218 reviews2 hours (approx.)From $44.00by WALKIN' WITH COLIN - A*SHOW*ON*THE*GO!

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Chicago, Tour Reviews, Tours, Walking Tours

Chicago: Treasures of the Golden Age Walking Tour

/ June 4, 2026

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.”

206 reviews2 hoursFrom $35by Chicago Architecture Center

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