Chicago Gangster and Food Walking Tour
Chicago Gangster and Food Walking Tour
Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Sample pizza; Chicago’s deep dish and historic tavern-style, prime steak, 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!
Book This ExperienceA glimpse of the journey
Your Itinerary
A curated journey through the experience
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 hourThe Magnificent Mile
Chicago's Miracle Mile, arguably one of the most beautiful food and shopping districts in North America. Guests will walk to Magnificent Mile on their way to Garretts Famous Popcorn.
20 minutesGold Coast
Try Chicago's iconic "Chicago Dawg" at one of it's oldest serving establishments in the beautiful and historic Gold Coast neighborhood.
20 minutesHoly 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 1930s. The bullet holes from the Tommy Gun are still visible in the side of the church today! Hear the story on our tour!
20 minutesIncluded
- Lunch - Four Different Tastings (Chicago Cut Steak, Chicago Dawg, Deep Dish Pizza, Garretts Popcorn
Not Included
- Alcoholic Beverages
Good to Know
- Not wheelchair accessible
- Service animals allowed
- Near public transportation
- Infants must sit on laps
- Most travelers can participate
- Paid stay-at-home policy for staff with symptoms
- Contactless payments for gratuities and add-ons
- COVID-19 vaccination required for guides
- This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
- This tour/activity will have a maximum of 15 travelers
- Confirmation will be received at time of booking
Tickets & Cancellation
You can present either a paper or an electronic voucher for this activity.
For a full refund, cancel at least 24 hours in advance of the start time of the experience.