Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago gangster tour to learn the true story. With an expert historian as your guide, you’ll visit the notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll also stop at former speakeasies, historic hotels, and even crime sites like that of the Saint Valentine’s Day Massacre.

Explore with a historian guide who’s an expert in Chicago gangsters
This private tour offers the most personal sightseeing experience
Choose from a range of departure times all throughout the day
Convenient pickup, drop-off, and private luxury transport included

What To Expect

The Loop

View Crime scenes immortalized in vintage news footage; the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the infamous St. Valentine’s Day Massacre.
30 minutes • Admission Ticket Free

Lincoln (Abraham) Park

Amazing stories of True Crime come to life on this tour. Guests will also have the unique experience of getting to visit many of the old venues that these gangsters used to operate out of. Including old speakeasies and historic hotels. The Chicago Crime and Gangster Tour includes your expert historian Guide and chauffeured Luxury transportation for a 3-hour minimum but the length of the experience can easily be extended at the client’s request.
30 minutes • Admission Ticket Free

Green Mill

Sit in Al Capone’s booth at the Green Mill.
15 minutes • Admission Ticket Free

Biograph Theatre

Visit the location where John Dillinger was shot.
15 minutes • Admission Ticket Free

Holy Name Cathedral

Holy Name Cathedral is part of Chicago’s notorious past. Legend says the hole in the exterior cornerstone stems from the 1926 murder of O’Banion protégé Earl “Little Hymie” Weiss on the church’s steps. To this day, some newlyweds place their finger in the hole for good luck.
15 minutes • Admission Ticket Free

Millennium Park

Take a photo with Cloud Gate, aka “The Bean!”
15 minutes • Admission Ticket Free

Highlight

Confirmation will be received at time of booking
Wheelchair accessible
The lux minivan can take between 13 to 28 people
Stroller accessible
Near public transportation
Most travelers can participate
This is a private tour/activity. Only your group will participate

Include

Hotel pickup and drop-off
Transport by private vehicle

Exclude

Gratuities