Chicago Prohibition Walking Tour 2 hr

Walk through Chicago’s Roaring Twenties and separate Prohibition myth from historical reality. This guided Chicago Prohibition Walking Tour connects the city’s famous gangster stories to the politics, reform movements, and social changes that shaped the era.

Begin at Pioneer Court on Michigan Avenue, then follow the story toward the DuSable Bridge and the Riverwalk, with Wacker Drive used when crowds require it. Hear how organized crime gained influence, learn about Al Capone’s rise during the Beer Wars, and revisit the St. Valentine’s Day Massacre with context beyond its Hollywood portrayals. The route also explores Chicago’s jazz legacy and the movement for women’s voting rights.

Along the way, see landmarks including the Chicago Theatre, Palmer House, Chicago Cultural Center, and Carbide and Carbon Building, as well as a location featured in The Untouchables. Stops offer time to hear the stories and take photos. With an English-speaking guide and wheelchair-accessible route, this Chicago Prohibition Walking Tour brings the city’s history to life on the streets where it unfolded. Join the walk to discover the people, places, and stories behind Chicago’s Prohibition reputation.