These destinations are designed to give you a glimpse of what once was, and introduce you to the infamous world of gangs and bootlegging.

A Gangster's Guide to Chicago

A Gangster’s Guide to Chicago

There are few reminders left that Chicago was once the home to the world’s most infamous gangsters like John Dillinger and Al Capone. Chicago was the perfect place for them to thrive, since the police force at the time was almost non-existent. Fortunately, that is no longer the scene in Chicago, but many gangster destinations still remain. So if you’re looking for a little notorious history lesson, hop on flights to Chicago and visit some of the famous sites and haunts of these gangs, as well as one of the many speakeasy-themed bars that remain from the Prohibition Era.

aerial view of downtown chicago

The Valentine’s Day Massacre

One of the most infamous episodes in Chicago’s history occurred on February 14, 1929. On this day, seven gangsters were killed within a garage in Lincoln Park. Known as the St. Valentine’s Day Massacre, this event allegedly began when Al Capone’s gang killed seven men. The assassins tricked the gangsters by dressing as police officers. While the goal of the assassination was to kill “Bugs” Moran, the assassins arrived too early to kill him. The original building is gone, but it is still an interesting place to visit.

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Mount Carmel Catholic Cemetery

No gangster tour would be complete without a trip to this cemetery. Placed in the Hillside neighborhood near Chicago, this cemetery is the final resting place of Al Capone. You’ll also find the burial sites of the Terrible Genna brothers and “Deany” O’Banion.

Union Station

Union station, Chicago

Today, Union Station is the home of Amtrak and Metra. Moviegoers may recognize this train station as the filming site of the gangster movie The Untouchables. While the actual incident and location were entirely fictionalized in Hollywood, it’s still an interesting stopping point for gangster fans –well worth searching out affordable flights to Chicago ASAP!

Biograph Theater

Placed at 2433 North Lincoln Avenue, the Biograph Theater is where the FBI once laid a trap for John Dillinger. When he left the movie theater, he pulled a weapon on the agents, and was gunned down. While it is currently the site of the Victory Gardens Theater, this location is also where Johnny Depp filmed Public Enemies.

RELATED: If you’re a true history buff then you’d definitely want to read more about the Best Museums to Check out in Chicago!

Tommy Gun’s Garage

If you want to experience the underbelly of 1920s Chicago first hand, visit Tommy Gun’s Garage. Designed with Prohibition furniture and décor, this speakeasy is a dinner theater that is set within the Prohibition era. Flappers, gangsters and old music are installed within the dinner theater for a more realistic ambiance. A little cheesy and a lot of fun, Tommy Gun’s Garage is worth a trip.

From Prohibition dinner theaters to the site of the Valentine’s Day Massacre, Chicago is filled with historic relics of the past. While the city has taken on a safer, law-abiding atmosphere, gangsters are a major part of Chicago’s history. So what are you waiting for? Start looking for cheap flights to Chicago to get a glimpse of what once was — the infamous world of gangs and bootlegging.

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