At the dawn of the 20th century, Chicago was booming with industry, immigrants, and innovation, but also with vice, crime, and corruption. Between 1900 and 1920, the city developed a reputation as one of America’s most notorious centers of organized vice. Gambling houses, brothels, and saloons flourished, often under the watchful eye—and protection—of the Chicago Police Department.
This era highlights the deep entanglement between politics, policing, and the underworld, setting the stage for the explosive rise of organized crime during Prohibition.
The Vice Districts of Chicago
Chicago’s vice economy was concentrated in a few infamous districts:
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The Levee District (near 22nd Street and the South Side): Known for brothels, gambling halls, and saloons.
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Custom House Place: Another red-light area, popular with sailors and laborers.
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“Little Cheyenne” and other small vice zones: Scattered across immigrant neighborhoods.
These districts operated openly, with police and politicians well aware of their existence. Many businesses paid regular protection bribes to police captains, ensuring they could operate without interference.
Brothels and the Sex Trade
Prostitution became a major industry in early 20th century Chicago.
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The Levee District featured luxurious brothels, some run by infamous madams like “Big Jim” Colosimo’s wife, Victoria.
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Brothels catered to all social classes, from wealthy businessmen to laborers.
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Immigrant women, often poor and desperate, were exploited in the trade.
Social reformers labeled this the era of the “White Slave Trade”, arguing that women were being trafficked into prostitution. Campaigns against prostitution gained steam, but police largely looked the other way until reformers forced crackdowns.
Gambling and Saloons
Gambling was another thriving enterprise.
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Saloons doubled as gambling halls, with poker, dice games, and slot machines.
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Bookmakers openly took bets on horse races.
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Gambling dens were frequently raided—but often reopened the next day after paying off police.
Saloons themselves were central to working-class Chicago life. By 1910, the city had more than 7,000 saloons, roughly one for every 200 residents. They provided cheap alcohol, social space, and sometimes even lodging.
The Role of Politics
Corruption thrived because Chicago politics and policing were deeply intertwined.
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Police captains were often expected to deliver votes for local aldermen and political bosses.
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Vice operators contributed campaign funds in exchange for protection.
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Reform efforts were often blocked by politicians with ties to saloonkeepers, gamblers, and brothel owners.
This relationship became known as the “Chicago System”—a network of politicians, police, and criminals who profited from vice.
The “First Ward Ball”
One infamous example of corruption and vice-politics collusion was the First Ward Ball, held annually from 1896 to 1908.
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Organized by corrupt aldermen “Bathhouse John” Coughlin and Michael “Hinky Dink” Kenna.
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The ball was a massive fundraiser attended by politicians, gamblers, pimps, and prostitutes.
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Fights, drunkenness, and debauchery were common.
Reformers used the First Ward Ball as a symbol of Chicago’s political corruption, and it was eventually shut down.
Police Corruption
The Chicago Police Department was at the center of this system.
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Officers often collected regular protection payments from saloons and brothels.
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Raids were staged for appearances but usually tipped off in advance.
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Honest officers found it difficult to rise in the ranks without political sponsorship.
The department became notorious for its brutality and selective enforcement, targeting working-class protests while tolerating vice.
Reform Movements
Despite entrenched corruption, reform movements grew in the early 20th century.
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The Chicago Vice Commission (1910–1911) published a major report exposing prostitution, estimating 5,000–10,000 prostitutes in the city.
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Religious groups and civic reformers pressured the city to shut down red-light districts.
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In 1912, the Levee District was formally closed, though prostitution and gambling simply moved elsewhere.
These reform campaigns reflected broader Progressive Era reforms, which sought to clean up urban corruption nationwide.
The Rise of Organized Crime
During this period, figures like “Big Jim” Colosimo emerged.
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Colosimo, an Italian immigrant, rose from a petty hustler to one of Chicago’s most powerful vice lords.
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He controlled brothels and gambling operations across the city.
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His connections with police and politicians ensured protection.
Colosimo’s empire would later become the foundation for the Chicago Outfit, the organized crime syndicate that dominated the city during Prohibition.
Legacy of the Era
The years 1900–1920 established several defining patterns for Chicago crime and policing:
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Police corruption tied directly to political machines.
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Vice economies tolerated or even encouraged as sources of profit.
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Reform movements struggling against entrenched interests.
This period laid the groundwork for the Prohibition era, when organized crime would expand dramatically, and the police would face even greater challenges.
