Chicago Gangster and Food Walking Tour

Chicago, US
95% of travellers recommend this
Excellent (469 reviews)

Included

  • inclusion
    Lunch

Excluded

  • exclusion
    Alcoholic beverages
  • exclusion
    Tour guide gratuity

Meeting Point

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

Meeting point

71 East W Wacker Dr, Chicago, IL 60601 , United States

End point

End Point

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

Meeting point

822 N State St, Chicago, IL 60610 , United States

End point

What to expect

1

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.

Duration 60 minutes
2

Gold Coast

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

Duration 20 minutes
3

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!

Duration 20 minutes

The experience can be subject to change due to bad weather or unforseen circumstances. We always endeavour to give you the best possible experience.

Additional Information

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

What our experts say

  • icon
    Try Giordano's for deep dish pizza nearby.
  • icon
    Visit the nearby Magnificent Mile for shopping.
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    Check out the street art in River North.
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    Bring a camera for unique photo ops!
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    Wear comfortable shoes for walking.

More About this Experience

Introduction

Experience the thrilling Prohibition Era in Chicago with the Chicago Gangster and Food Walking Tour. This unique tour takes you through one of the most fashionable and notorious neighborhoods of the time while indulging in Chicago's iconic cuisine. From prime steak to deep-dish pizza and the famous "Chicago hot dog," taste the flavors that made this city famous. As you walk the streets once frequented by Al Capone and his gang, uncover the secrets and stories behind the prohibition era. Get ready to step into the underworld of Chicago and satisfy your taste buds on this one-of-a-kind tour.

What to expect?

On this tour, expect to immerse yourself in the history and flavors of Chicago. Lasting for 120 minutes, the itinerary takes you through different steps of gastronomic pleasure. You'll start in the River North neighborhood, home to iconic restaurants and significant gangster history. Indulge in prime steak at Harry Caray's steakhouse, once an Al Capone hideout with a secret tunnel used by gangsters. Savor deep-dish pizza in an old gangster's mansion turned iconic pizzeria. Then, head to the historic Gold Coast neighborhood to try the famous "Chicago Dawg" at one of the oldest serving establishments. Along the way, stop at the Holy Name Cathedral, where a notorious gangster was gunned down in the 1920s. Take in the sights as you cross the Chicago River, surrounded by stunning skyscrapers.

Who is this for?

This tour is perfect for anyone with a love for history, food, and adventure. Whether you're a local wanting to explore your city in a new way or a visitor looking for an authentic Chicago experience, this tour is for you. It's an opportunity to discover Chicago's culinary heritage while learning about its infamous past. The tour is designed to be inclusive and enjoyable for people of all ages and backgrounds. Whether you're a solo traveler, part of a group, or on a romantic getaway, come join us to uncover the secrets and flavors of Prohibition-era Chicago.

Why book this?

Step back in time and dive into the captivating world of Chicago's gangster history on this immersive food walking tour. Not only will you taste the iconic foods that put Chicago on the map, but you'll also walk in the footsteps of notorious gangsters and visit locations that played a significant role in the Prohibition Era. Let your senses be awakened by the rich flavors, tantalizing aromas, and compelling stories that have shaped this city. With a passionate and knowledgeable guide leading the way, every step will be filled with excitement and intrigue. This tour is a chance to experience the best of Chicago's cuisine while uncovering the hidden tales of its past, making it an unmissable opportunity for both locals and visitors alike.

Good to know

Please note that the total duration of the tour is 120 minutes. The meeting point is in front of "Hoyt's" at the Royal Sonesta Hotel, conveniently located across from the Chicago River. The tour takes you through various neighborhoods, providing not only delicious food stops but also opportunities for sightseeing and exploration. The tour ends just two blocks from the Magnificent Mile, a vibrant area perfect for continuing your Chicago adventures. Don't forget to wear comfortable shoes and bring along your appetite as you embark on this fascinating journey through Chicago's history and cuisine.

Reviews

Feedback from previous participants attests to the exceptional experience offered by the Chicago Gangster and Food Walking Tour. Visitors have raved about the knowledgeable guides, who bring the stories and history to life, making the tour engaging and entertaining. The combination of delicious food and intriguing tales makes for an unforgettable outing. Travelers have praised the selection of food stops, from the legendary Harry Caray's steakhouse to the mouthwatering deep-dish pizza served in a historic gangster's mansion. The opportunity to visit significant locations, such as the Holy Name Cathedral and crossing the Chicago River, has been mentioned as highlights of the tour. Overall, reviews highlight the tour as a must-do in Chicago, providing a unique and immersive experience that blends history, culture, and cuisine seamlessly.

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