Tours/Chicago/Chicago: Gangsters and Food Tasting Walking Tour
Viator · group up to 25 pax

Chicago: Gangsters and Food Tasting Walking Tour

4.8(6)Chicago1 hour
VIATOR5.0(1)TRIPADVISOR4.8(5)

Description

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 two types of pizza - Chicago’s deep dish and historic tavern-style – 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 a 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.

Tour Options

Chicago: Gangsters and Food Tasting Walking Tour

Itinerary

30 min

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.

30 min

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.

30 min

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.

Highlights

Expert tour guide
Meals

What's included

Included
Expert tour guide
Meals
Not included
Alcoholic Beverages
Gratuities

Traveller Ratings

4.8
6 reviews
5
5
4
1
3
0
2
0
1
0

Important Information

  • Wheelchair accessible
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Suitable for all physical fitness levels

Reviews(6)

3
368reesag
July 4, 2026
700 out of 10

If I could give more stars, I absolutely would. Peyton was our guide and she nailed it! Funny, friendly, and informative - I could not have asked for a better guide. Food was great! My mom is 81, and we were a little worried about the walking part of it, but it was fine for her too! Enough breaks and a slow enough pace. Please go!!

D
daniellefI5959BK
July 3, 2026
Rain AND shine!

Peyton was a real trooper. It rained for the first half of the tour but she carried on!

Y
Y6666JVcaitlinb
July 3, 2026
Food and friends in the Windy City!

We had a blast! Food was great and Baylor was an excellent tour guide. She was a fantastic storyteller and provided a great experience!

O
O5077MPcamilleh
July 1, 2026
Hot but fun time

Our tour with Baylor was great she was very knowledgeable and friendly.

F
Footprints375947
June 29, 2026
Learn more about the city and eat too!

Great mix of history and food- guide Brailor was great. Historical details were fun and she was knowledgeable.

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