Chicago Gangster and Food Walking Tour | 2 hours

472 Reviews | Chicago
Select Date and Travelers
You can select up to 15 travelers in total.
Senior (65-99) Minimum: 0, Maximum: 15
0
Adult (18-64) Minimum: 1, Maximum: 15
2
Youth (7-17) Minimum: 0, Maximum: 15
0
Infant (0-6) Minimum: 0, Maximum: 15
0
Free Cancellation For a full refund, cancel at least 24 hours before the scheduled departure time.
Chicago Gangster and Food Walk
2 Adults x $75.00
$150.00
Approx Total
$150.00

Inclusions / Exclusions

  • Mobile ticket
  • Offered in: English
  • Three Different Tastings (Chicago Prime Cut Steak, Chicago Hot Dog, Deep Dish Pizza)
  • Alcoholic Beverages
  • Tour Guide Gratuity

Overview

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Sample prime steak, deep dish pizza and the world famous “Chicago hot dog" while treading the streets of Capone’s closest friends and dreaded enemies. Even visit an old tunnel used by prohibition gangsters in the basement of one of the establishments! Learn about Chicago's world famous cuisine and the gangsters who ate it all in one special unique tour!

Meeting points

The tour meets outside of "Hoyt's Tavern" next to the Royal Sonesta Hotel, your guide will be waiting for you here!

End point

Open in Google Maps

Ends two blocks from the Magnificent Mile. About a 15 minute walk from where we started.

Itinerary

  • River North

    Chicago's famous River North neighborhood containing many of Chicago's most iconic restaurants, food and gangster history. Travelers will eat at Harry Caray's steak house, an old hideout for Al Capones men with a secret tunnel used by gangsters in the 1920s and 1930s which the guests will see. Also we will have deep dish pizza in an old gangster's mansion that was converted years ago into one of Chicago's most iconic Pizzeria restaurants.

    1 hour

  • Gold Coast

    Try Chicago's iconic "Chicago Dawg" at one of it's oldest serving establishments in the beautiful and historic Gold Coast neighborhood.

    20 minutes

  • Holy Name Cathedral

    On route to one of our food stops we will stop in front of this beautiful church where one of Chicago's most notorious gangsters was gunned down in the 1920s. The bullet holes from the Tommy Gun are still visible in the side of the church today! Hear the story on our tour!

    20 minutes

Sample Menu

Additional Info

  • Service animals allowed
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels

Free Cancellation

June 18100% refund
June 19No refund

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Traveler Photos
Reviews

4.8

472 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews
  • 5 stars
    413
  • 4 stars
    39
  • 3 stars
    9
  • 2 stars
    5
  • 1 star
    6

Reviews by TravelOne travelers

Showing 1-5 of 413 reviews with 5 stars

So Good I Did it Twice!

Published on Jan, 2025

GREAT TOUR! This tour is so good I went a second time when friends came from out of country. Alan was a great tour guide (again!) and I would gladly do it a third time if more first-time to Chicago friends come to town.

perfect combo of food and history

Published on Jan, 2025

It was such a great time, even in the cold it was the perfect mix of great food, great history and great laughs. Allan our tour guide was amazing!

Great fun! Must do

Published on Jan, 2025

I booked this for my 16 year old son and I. Alan was a fabulous guide. Really fun day out even despite the cold - dress warm (in January). Yummy food, great gangster chats and fun group. A Chicago must do in my opinion.

Great Tour

Published on Jan, 2025

We enjoyed this tour. Our guide, Ty, was knowledgeable and funny and the food was great! Fun part of the city to explore. I would recommend this tour.

Give Ty a big Bonus!! He...

Published on Dec, 2024

Give Ty a big Bonus!! He was awesome! Very informative, knew the subject, added his own twist. Chantal and Jill.

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