Chicago: Gangsters and Food Tasting Walking Tour

4.7
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37
Reviews
Recommended by 89% travellers
89% of guests rated this experience 4 stars or higher
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4.7  (37)
Recommended by 89% travellers
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4.7
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37
Reviews
Recommended by 89% travellers
89% of guests rated this experience 4 stars or higher
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4.7  (37)
Recommended by 89% travellers
Available TodayReserve your spot now and join the experience today.
Free CancellationCancel for free up to 1 day before your experience
Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world
Why book with byFood?
Japan's #1 food travel platform
Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT
Duration
2 hours
Group size
Max 15 guests
Language
English
Duration
2 hours
Group size
Max 15 guests
Language
English

Why travelers loved this

4.7
•37 reviews
 US$79.54  per guest
Instant Confirmation
Select Options
Available TodayReserve your spot now and join the experience today.
Free CancellationCancel for free up to 1 day before your experience
Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world
Why book with byFood?
Japan's #1 food travel platform
Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT
Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine and the gangsters who ate it all in one special unique tour! Sample Chicago’s deep dish – as well as prime steak and the world famous “Chicago hot dog" all while treading the streets of Capone’s closest friends and dreaded enemies. Highlights include a visit to an old tunnel used by prohibition gangsters in the basement of one of the establishments; a mansion once used as a brothel for gangsters; the Cathedral where gangsters were gunned down by Capone’s men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000’s. Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)
Expert tour guide
Meals
Alcoholic beverages
Alcoholic Beverages
Gratuities
1
30 minutes · Admission Ticket Free

Harry Caray's Italian Steakhouse

Step into the historic Harry Caray's Italian Steakhouse on West Kinzie Street—a building famously tied to notorious mob boss Frank Nitti. Savor a delicious, perfectly prepared steak tasting while your guide shares captivating tales of Chicago's rich culinary and gangster history. Meat options can be made gluten-free
Step into the historic Harry Caray's Italian Steakhouse on West Kinzie Street—a building famously ti…
2
30 minutes · Admission Ticket Free

Pizzeria Due

Stop at the famous Pizzeria Due on North Wabash Avenue for the ultimate Chicago experience: authentic deep-dish pizza! Savor a mouth-watering slice of this iconic, thick-crusted masterpiece while your guide shares captivating stories of the city's rich culinary and mobster history. Gluten-free option available. Please note: It is cooked in a shared oven with non-GF ingredients
Stop at the famous Pizzeria Due on North Wabash Avenue for the ultimate Chicago experience: authenti…
3
30 minutes · Admission Ticket Free

Mister J's

Stop at Mister J's on North State Street for an authentic, fully loaded Chicago-style hot dog. Savor this quintessential local bite while your guide shares thrilling stories of the city's notorious gangster history. Gluten-free? We've got you covered, just ask for your hot dog served bunless!
Stop at Mister J's on North State Street for an authentic, fully loaded Chicago-style hot dog. Savor…
Meeting Point

71 E Wacker Dr, East Wacker Drive, Cook County Illinois, United States, US, 60601

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Please meet your guide outside "Hoyt's Tavern" 15 minutes before the start time: 71 E Wacker Dr, Chicago, IL 60601, USA.
End Point

822 N State St, North State Street, Cook County Illinois, United States, US, 60610

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Mister J's Hotdogs is where the tour will end
Free cancellation
Cancel up to 1 day before for a full refund.
No refund within 1 day of the experience or no-shows.
4.7
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37 reviews
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37 reviews
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Compass507370September 2026 • TripAdvisor
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Beautiful experience

The history of the Italian and Irish gangster gangs is very captivating and the tastings of local specialties are excellent

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NorthStar17151064659September 2026 • TripAdvisor
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Gangster Food Tour

Guide was very knowledgeable of Chicago history.

F
Flyer57510229247September 2026 • TripAdvisor
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The Outfit Legends

Peyton was a fantastic tour guide. She has a bubbly personality and is well versed in the gangster stories. The food was enjoyable. We had steak, pizza, and a hotdog. The walking was at an easy pace. I would definitely recommend this tour.

D
DeAnna_HSeptember 2026 • Viator
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Gangsters

Enjoy the knowledge you get about the gangsters here from Baylor. Easy walking and yummy tastes for your belly.

R
robertchanelnSeptember 2026 • TripAdvisor
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Great Chicago food

Loved the food choices!! Know before you go that you like the food in the description

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