Ever wanted to walk in the footsteps of major league gangsters with colorful nicknames like Al “Scarface” Capone, Frank “the Enforcer” Nitto, or “Greasy Thumb” Jake Guzik? How about big time flesh peddlers and saloon keepers like the Everleigh sisters, Victoria Shaw, or Mickey Finn? On this walking tour, you’ll go back in time to Chicago’s ragtime and jazz eras to do exactly that. Along the way, you’ll hear stories about the assorted pimps, procurers, madams, and slumlords who ran the ill-famed Levee Red Light vice district, and the bootleggers, traffickers, card sharks, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit.” This circular walk takes you through Chicago’s Motor Row and Prairie districts, leading you to or telling you about sites including: • Saloons like the original Bucket of Blood and Mickey Finn’s • Brothels and bagnios, both posh and fleabag • Speakeasies like Al Capone’s Four Deuces and Hymie Jacobs’ • A dance hall which served as the center of a vast white slave trade • Several of Capone’s “headquarters” including the infamous Lexington hotel • Hourly hotels that catered to transient sex workers who were known as “roomers” • Capone’s Depression-era “soup kitchen” for the unemployed No soup kitchens for you! There are plenty of cafes, restaurants and bars along this 1.5 mile trip for quick or lengthier stops, and Chinatown is a few blocks away. Join me on this tour and discover why early twentieth-century Chicago had the largest Red Light vice district in the entire world, and the most notorious Prohibition gangsters and mob connections!