What Are the Famous Gangster Sites in Chicago?

Are you a fan of gangster history? Do you want to know about the famous gangster sites in Chicago? Well, you’ve come to the right place. In this article, we will take a trip back in time to explore the notorious world of Chicago’s gangsters. From the underground speakeasies to the hidden gambling dens, we will uncover the secrets of the Windy City’s criminal past. So, put on your fedora and join us as we delve into the history of Chicago’s most infamous gangster sites.

The Green Mill Cocktail Lounge

One of the most famous gangster sites in Chicago is the Green Mill Cocktail Lounge. Located in the Uptown neighborhood, this historic jazz club was a favorite hangout spot for gangsters during the Prohibition era. It served as a meeting place for notorious figures such as Al Capone and his associates. The Green Mill still stands today, preserved as a reminder of Chicago’s glamorous yet dangerous past.

The St. Valentine’s Day Massacre Site

No discussion of Chicago gangsters would be complete without mentioning the St. Valentine’s Day Massacre site. On February 14, 1929, seven members of the North Side Gang were brutally murdered at a garage located at 2122 North Clark Street. This infamous event marked the peak of the gang wars between Al Capone’s South Side Gang and the North Side Gang led by George “Bugs” Moran. The site of the massacre is now a tourist attraction, allowing visitors to step back in time and learn about this tragic event in Chicago’s history.

The Biograph Theater

The Biograph Theater is another famous gangster site in Chicago. On July 22, 1934, the notorious bank robber and gangster John Dillinger was shot and killed by federal agents outside the theater. Dillinger had just watched a movie at the Biograph when he was recognized and apprehended. The theater still operates today, serving as a reminder of the city’s connection to organized crime during the 1930s.

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The Lexington Hotel

The Lexington Hotel played a significant role in Chicago’s gangster history. It was the residence and headquarters of Al Capone, the most notorious gangster of the 1920s. Capone operated his criminal empire from the hotel, using it as a base for his illegal activities. While the original Lexington Hotel no longer exists, its legacy lives on, attracting tourists eager to explore the world of Al Capone and the Chicago Outfit.

Union Stockyards

The Union Stockyards was not only a famous gangster site but also a major hotspot for illegal activities during the Prohibition era. This vast meatpacking complex served as a cover for bootlegging operations and other criminal activities. Gangsters like Al Capone controlled the supply and distribution of illegal alcohol, using the Union Stockyards as a hub. Although the stockyards are no longer in operation, their historical significance can still be felt in Chicago.

The Palmer House Hotel

The Palmer House Hotel has a rich history intertwined with Chicago’s gangster past. It was a popular meeting place for gangsters and politicians alike. The hotel’s Empire Room was a favorite spot for high-profile gangsters to socialize and enjoy live entertainment. While the original Palmer House Hotel was destroyed in a fire, it was later rebuilt and continues to be a prominent landmark in the city.


Chicago’s gangster sites offer a fascinating glimpse into the city’s criminal history. From the Green Mill Cocktail Lounge to the St. Valentine’s Day Massacre site, each location carries a unique story of the city’s notorious past. Whether you’re a history buff or just curious about the world of gangsters, a visit to these famous sites is a must. So, pack your bags and get ready to immerse yourself in the captivating world of Chicago’s gangsters.

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