Chicago's Original Gangster Tour Chicago | Tickets & Tours | Headout
All Categories
Best Sellers
Download app
The world on your tapGet the Headout app to get tickets on your phone and access app-only deals. Talk about win-win.

Chicago's Original Gangster Tour


  • Listen to spine-chilling tales of Al Capone and Dillinger
  • Visit the site of the 1929 St. Valentine's Day Massacre
  • See the old gangster hotspots and live the excitement of old jazz-age Chicago


  • Tour Guide


  • Hotel pickup and drop-off
  • Gratuities

Explore the eerie gangster and crime history of Chicago through Crime Tour. Take a ride back to the Prohibition Era of the 1920s and visit the city's most macabre sites. Find out more about the infamous Al Capone and others.

my tickets

Please provide the name under which the reservation was made after reaching the pick up location.

additional information

Please arrive 15 minutes prior to the tour time
This tour is recommended for high school age students or older

Missing any information?
This experience is unavailable
You'll be the first to know when these tickets are back online.
Notify Me
Awesome!We will notify you.
Why Headout?
Trusted platform used by 100K+ people, each month
Get the lowest prices and last minute availability
Discover and connect with 10,000+ experiences
Browse verified reviews and professional photographs
Have a question? Live chat with our experts 24/7
We've served 9 million+ guests and we are here for you
9 million +Happy customers across 10,000+ experiences

5,000+ verified reviews with 90% excellent score

In the mediaFeatured and recommended by the best brands

24 x 7 help CenterHave a question? Live chat with local experts anywhere, anytime