Chicago: Gangsters and Food Tasting Walking Tour

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Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious gangster-ridden neighborhoods in Downtown Chicago.


  • Learn the history behind Chicago's most iconic foods and the food tasting venues
  • Taste Chicago staples like juicy steak, hot dogs, and Chicago deep dish pizza
  • Hear stories about Chicago‚Äôs most famous gangsters
  • Enter old gangster hideouts including an old underground tunnel used by Capone
  • See where gangsters relaxed, did deals or maybe met a sticky end


Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era‚Äôs 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‚Äôs deep dish and historic tavern-style ‚Äď as well as prime steak and the world famous ‚ÄúChicago hot dog' all while treading the streets of Capone‚Äôs 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‚Äôs men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000‚Äôs.


Three food tastings Water and soft drinks Expert local guide Tours of old Al Capone hide outs Food & Gangster History in Chicago's River North neighborhood

Important Information

  • The tour is a walking tour about 1 mile long, with 4 stops. Food tastings add up to a good lunch meal Tour departs rain or shine

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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