The Lexington Hotel in Chicago was a grand ten‑story hotel built in 1892 that later became infamous as the headquarters for gangster Al Capone during the Prohibition era, when bootlegging and organized crime flourished in the city. From 1928 to 1931, Capone and his crew operated out of the hotel’s upper floors, using it as a base for running illegal liquor operations and other rackets during the dry years of the 1920s. After Prohibition ended and Capone was imprisoned, the Lexington’s reputation declined, and the building was eventually demolished in 1995, but its history remains a compelling part of Chicago’s Prohibition story.

The Green Door Tavern in Chicago is one of the city’s oldest bars, with origins dating back to 1872 and a storied connection to Prohibition. During the 1920s, when alcohol was outlawed nationwide, the Green Door gained a reputation as a hidden speakeasy, offering illicit drinks behind its unmarked door and drawing patrons eager to beat the dry laws. Today, the tavern embraces its legacy with a historic atmosphere, making it a must‑visit destination for visitors seeking authentic Chicago nightlife and Prohibition‑era history in a classic neighborhood setting.

The Green Mill in Chicago is a legendary bar with deep roots in Prohibition-era history. Established in 1907, it became a favorite hideout for mobsters and jazz musicians during the 1920s, offering illegal speakeasy-style drinks and live music. Today, the Green Mill continues to celebrate its historic Chicago Prohibition past, making it a must-visit spot for those exploring the city’s nightlife and history.