Bullet Holes & Bosses: A Gangster Tour, 20 December | Event in Chicago | AllEvents

Bullet Holes & Bosses: A Gangster Tour

Chicago Mafia History

Highlights

Sat, 20 Dec, 2025 at 07:00 pm

Chicago History Museum

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Date & Location

Sat, 20 Dec, 2025 at 07:00 pm (CST)

Chicago History Museum

1601 North Clark Street, Chicago, IL, United States

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About the event

Bullet Holes & Bosses: A Gangster Tour
Step into the real story of Chicago’s underworld. This gangster bus tour, led by Chicago historian Tony Szabelski and AJTrueCrime takes you deep into the violent past of the city’s most notorious mobsters. You’ll hear the real history behind the outlaw exploits of John Dillinger, the brutal North Side wars with Bugs Moran, and the rise of the Outfit under Al Capone.

The tour also highlights the power and influence of major Outfit bosses, including Frank Nitti, Paul Ricca, Tony Accardo, and Sam Giancana. We’re not revealing our locations ahead of time, but every stop is connected to a pivotal moment in Chicago’s mob history: hits, betrayals, power struggles, escapes, and the stories that built the Outfit’s empire.

This event is built for the ultimate mafia and gangster history fans. If you're interested in joining us please send a message to AJ or Tony.

Date: 12/20
Time: 7:00PM
Cost: $50

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Chicago History Museum, 1601 North Clark Street,Chicago,IL,United States
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Chicago Mafia History

Chicago Mafia History

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Bullet Holes & Bosses: A Gangster Tour, 20 December | Event in Chicago | AllEvents
Bullet Holes & Bosses: A Gangster Tour
Sat, 20 Dec, 2025 at 07:00 pm