This tour stands out by pairing Chicago Prohibition era history with the city’s most famous foods—a rare combination. Tour the fashionable River North neighborhood while sampling local specialties at historic “gangster” hideouts: think of a steakhouse with a secret tunnel, and deep dish pizza in an old “gangster’s” mansion.
- A small-group “gangster” and food walking tour in Chicago
- Visit a historic steakhouse, deep-dish pizza spot, and more
- Travel with a guide: Learn about Chicago’s “gangster” history
- Small group ensures more personalized attention from your guide
What To Expect
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 • Admission Ticket Free
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 • Admission Ticket Free
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 • Admission Ticket Free
Highlight
Confirmation will be received at time of booking
Not wheelchair accessible
Service animals allowed
Near public transportation
Infants must sit on laps
Most travelers can participate
This tour/activity will have a maximum of 15 travelers
Max group – 15
