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Tours & experiences

Chicago: Gangsters and Food Tasting Walking Tour

About this experience

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.)

At a glance

  • Duration: 2 hr

What is included

  • Expert tour guide
  • Meals

Not included

  • Alcoholic Beverages
  • Gratuities

Itinerary and highlights

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

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 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!

Meeting and pickup information

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

Languages and tickets

  • English — Guide
  • Mobile Only

Tour operator

  • Empire Tours - Chicago

Accessibility and practical details

  • 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
  • Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Available tour options

  • Private Tour: An exclusive, private experience created solely for your group!

Traveller reviews and photos

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