The Wicked City: Vice, Crime and Gangsters in Nineteenth-Century Chicago

Chicago's storied underworld didn't begin with Al Capone—it was woven into the city's fabric from its earliest days. On this captivating walking tour through the northern Loop, you'll discover the darker side of 19th-century Chicago, from lawless vice districts to corrupt politicians and early crime bosses. Follow the footsteps of gamblers, gangster predecessors, and saloonkeepers who shaped the city's notorious reputation.

The tour starts at the DuSable Bridge, formerly known as the Michigan Avenue Bridge, where Chicago's first settlement began. You'll walk across the river and into the heart of the old vice districts, including the infamous Sands shantytown where the city's earliest brothels and gambling dens flourished. Along the way, you'll trace the development of Chicago's criminal underworld from its rough-and-tumble frontier beginnings through the emergence of organized crime.

You'll hear about the violent 1855 Lager Beer Riot when German immigrants protested anti-alcohol laws, and explore the notorious hangouts of crime bosses like Sure Thing Michael McDonald, whose gambling empire operated with impunity. The tour ends at the site of Chicago's devastating 1857 fire—a disaster started by an unnamed prostitute that preceded the more famous Great Chicago Fire of 1871.

On this 90-minute journey through Chicago's wicked past, you'll have a chance to:

• Walk through the former Kilgubbin shantytown where generations of criminals and future political bosses got their start
• Learn how prostitution flourished along South Water Street, where farmers came to sell their grain and spend their profits
• Visit the location of the Silver Dollar Saloon, where corrupt alderman Bathhouse Coughlin conducted city business
• Explore The Store, the gambling den that functioned as Chicago's unofficial city hall under crime boss Michael McDonald
• Take a pitstop at one of Chicago's classics - The Billy Goat tavern
• See the spot where the Great Chicago Fire jumped the river, nearly destroying the entire city
• Hear scandalous stories from a recently discovered diary documenting Chicago's vibrant 19th-century gay community
• Stand where the 1857 fire began, when an angry prostitute set her bed aflame after a customer refused to pay

Discover the colorful characters and notorious places that earned Chicago its reputation as the wickedest city in the United States. This walk through history reveals how vice, corruption, and crime shaped the city we know today.