Chicago Mobsters and Movies Walking Tour

Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then shows you how the very same streets turned into movie magic. Walk the same corners seen in 'The Untouchables' and 'Public Enemies,' and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both.
Your guides aren’t just storytellers—they’re trained true crime historians, film buffs, and Chicago insiders who bring every scene to life. Step inside exclusive interiors where real mobsters plotted and Hollywood crews once brought the Windy City to the Silver Screen. We take you deeper into the story than any other tour can. Expect vivid tales, insider trivia, and behind-the-scenes stories that make Chicago’s gangster past feel as real as the movies it inspired.

Meeting Point

238 N State St

238 N State St, Chicago, IL 60601, USA

Corner of State Street and Wacker Drive. Your host will be standing in front of Chase Bank.

What's included:

• Souvenir Photos

Not included:

• Tip/Gratuity for Tour Guide

What to expect:

Duration: 1 hour, 30 minutes

238 N State St

238 N State St, Chicago, IL 60601, USA

The Chicago Riverwalk is one of Chicago's most famous and filmed landmarks. Hear you will explore a few mob stories and movie locations that still stand along the famous riverwalk.

15 minutes

River North

Chicago, Illinois

Discover underground tunnels used by the Chicago Outfit, and visit where John Dillinger saw his girlfriend for the very last time. Movie locations will include 'The Dark Knight' and 'The Fugitive.'

10 minutes

The Picasso

50 W Washington St, Richard J. Daley Plaza Civic Center, Chicago, 60602-1305, Illinois

This icon of the city is also the filming location for some of Chicago's most famous movies. We will revisit those scenes from 'The Fugitive,' 'The Blues Brothers,' and 'Ferris Bueller's Day Off' as we also explore true crime legends that have lurked in this corridor of power.

10 minutes

The Rookery Building

209 S La Salle St, , Chicago, 60604-1219, Illinois

Chicago's business district is also the backdrop for some of the most exciting Chicago movie scenes, ranging from 'The Dark Knight' to 'The Untouchables.' We will see beautiful architectural interiors as we uncover famous Chicago mob characters along the way.

15 minutes

The Art Institute of Chicago

111 S Michigan Ave, Chicago, 60603-6110, Illinois

We will talk about the history of the Art Institute and Chicago's cultural mile as it relates to some of the most famous crimes in Chicago history. We will also talk about how to make the most out of a visit to the Art Institute to visit art pieces used in famous movies.

15 minutes

The Chicago Theatre

175 N State St, , Chicago, 60601-3623, Illinois

This city landmark has rich Al Capone history, as well as the filming location for countless live music and comedy albums. As a filming location it has also captured audiences in 'Public Enemies,' and 'The Dark Knight.'

10 minutes

Chicago Cultural Center

78 E Washington St, , Chicago, 60602-4801, Illinois

We end the tour at the filming location of the climactic scene for 'The Untouchables,' a perfect blend of Mobsters and Movies. We visit the architectural wonders inside the former Chicago Public Library, including the largest Tiffany glass dome in the world, and other art exhibits.

10 minutes