Private Chicago Gangster and Prohibition History Tour
Discover Chicago's infamous gangster past on a private, fully customized tour of the city's historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events from the 1920s and 1930s. Start at the Biograph Theater, where John Dillinger was shot, then visit the site of the St. Valentine's Day Massacre, a pivotal moment in the rise of Al Capone. Explore the Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray's Italian Steakhouse, all tied to Chicago's mob history. Conclude in the Chicago Loop, discovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible door-to-door itinerary, this private tour offers an immersive and exciting look at the city's dramatic gangster history.