Red Lighting Chicago Vice

By Darryl Holliday

In 1900, at the age of 21 and 23, Ada and Minna Everleigh moved to Chicago and began the most famous brothel in the country. When they closed the famed whorehouse and left the city in 1911, they had more than $1 million in cash, jewelry and stock, while a wider ring of vice remained in their place.

There was a time in the city when 50 cents would buy a ticket to see pretty much anybody doing anything, and though it’s hard to tell Chicago’s seamy fact from fiction, at least some of the scandal is true: Prostitutes were plentiful, and Chicagoans could indulge their vices at any number of legitimized locations scattered around town without police interference.

The Windy City’s lurid flirtation with red light districts—selective areas where prostitution, brothels and general indecency were tolerated by police and the public—spanned more than 30 years, peaking around the 1900s. Notorious bailiwicks—such as the Levee district, nowadays part of Chinatown; and The Sands, once located along the shore of Lake Michigan—catered to Chicagoans’ more disreputable desires, leaving traces of prostitution and other crime that continue to exist in certain areas today.

“There’s hardly a neighborhood or street around the city that wasn’t a red light district at some point in history,” said Bill Griffith, Chicago historian.

As early as the 1840s, small pockets of vice could be found in Chicago. By the next decade, areas along the southern edge of the Loop, including Madison Street and Printer’s Row, had become infamous partially because of vice areas such as the Custom House district, which had its epicenter around Dearborn Station, 47 W. Polk St.

The region south of today’s Harold Washington Library Center, 400 S. State St., was known as “Hell’s Half-Acre,” and contained some three or four dozen brothels, whiskey bars, pawn shops and opium dens crammed into a half block, according to Griffith.

“Everything in the South Loop was just horrible for a long time,” he said.

Likewise, State Street—from Roosevelt Road to the mid-South Side—was once known as “Satan’s Mile” after its more deplorably enticing features, which included prostitution, gambling, drinking and other wanton depravity.

The Everleigh sisters ran the notorious Everleigh Club, a high-class brothel located on the 2100 S. Dearborn St. block. They occupied the upper-end of the red light spectrum, charging customers exorbitant fees for sex as long as they were rich and white.

“[The Everleigh Club] was the really fancy one, where if you spent less than $50 a night—and that’s like, $50 in 1900 money—you would be banned for life,” Griffith said.

Other madams, such as Black Susan Winslow, owner of a brothel underneath the Clark Street viaduct, currently the South Loop Target store on Roosevelt Road, held down the dregs. Black Susan is said to have been a nearly 500 pound woman who evaded arrest because police were unable to remove her from the building.Her story, while dubious, is rife with an amalgum of sex and crime.

“[Winslow’s brothel] was one of the places where instead of getting f***ed, you’d get robbed,” Griffith said.

Before the White-Slave Traffic Act of 1910, Chicago had all but legalized prostitution, according to Ken Melvoin-Berg, creator of Weird Chicago, which offers local bus tours displaying a mix of ghosts, crime and unusual Chicago history year-round.

Better known as the Mann Act, the federal legislation prohibited white slavery and the transportation across state lines of females for “debauchery” and “immoral purposes.” A common use of the act was to prosecute men for having sex with underage women, and limit prostitution and child pornography, all of which had previously been running rampant in Chicago’s vice districts.

“Chicago was one of the areas in the U.S. that was seen as such a dirty town because we had a very corrupt political and law enforcement subset that would deal directly with prostitution,” Melvoin-Berg said.

During the 1890s, Aldermen “Hinky Dink” Kenna and “Bathhouse John” Coughlin, of the 1st Ward, held an annual party called the First Ward Ball, where they used local hookers to raise money for their campaign war-chests.

According to Melvoin-Berg, the name of a popular Chicago music festival originated with these parties when Kenna was quoted as saying, “It’s a lollapalooza,”—during a year when nearly 50,000 residents showed up for the drunken orgy.

“The police were generally known to look the other way,” Griffith said. “It was more or less legal in most areas around there.”

Largely accepted by law enforcement, local government and the public, the districts went unchecked for decades—the prevailing notion being that if a certain area existed solely for indulgence, other areas would remain relatively smut free.

But the theory hardly worked out in practice.

When red light districts were shut down in Chicago and elsewhere during the 1910s and ‘20s, the effect was to spread the vice across the city. Today’s more licentious communities can be traced to this shift.

The intersection of North and Ashland avenues is currently a center of prostitution in Chicago, according to Melvoin-Berg. Other hubs can be found on The Far West Side, the Far South Side including Pullman and the Bucktown/Wicker Park area.

“In some ways [the red light districts] still exist,” he said. “Not legally but illegally—it’s split in different areas of the city.”

Modern day red light districts take form in areas populated by adult novelty stores, happy ending massage parlors and bondage dungeons, among others. Stores such as The Pleasure Chest and Skyscraper Heels, in Roscoe Village, cater to the sado-masochistic, corset-loving, anal-beading,dildo-rocking, dominant/submissive in all of us.

But Chicago’s gaudy history offered sex in a way that can’t be found in such legitimized grandeur these days.

Nowadays, prostitutes average $27 a trick and are more likely to solicit business on the Internet, especially on sites like Facebook, according to Melvoin-Berg. However, they continue to be highly susceptible to abuse, homelessness, drug abuse and physical and mental problems.

While the madams and whorehouses of Chicago’s 1900s no longer exist in the same form, they have been replaced with pimps and streetwalking hookers in many areas of the city, though not much is known about the prostitution industry nationwide.

“[Take] me back in time and I could get you to a whorehouse without much trouble,” Griffith said. “Today, I’m not sure where you’d go.”

A listing of prostitution arrests and descriptions of the statutes that govern prostitution law can be found at