Chicago’s Classic Dives
This is part of a series on Chicago’s dive bars. Click here to read about 14 classic Chicago dives and stay tuned for Part Three tomorrow.

CHICAGO — Since the days of early settlers, saloons have been a part of Chicago.

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In the late 1820s and early 1830s, a number of taverns existed near Wolf Point — the confluence of the Chicago River’s three main branches — including Wolf Tavern, Miller’s Tavern, Eagle Exchange Tavern and the Green Tree Tavern. The area is now known as River North.

Yet, not all saloons were friendly neighborhood joints where everyone knew your name.

While taverns, saloons and pubs had their opponents, “dives” were known as the worst of the worst. The term, first appearing in the 1870s, was used to refer to a spate of unsavory businesses, including brothels, sleazy lodging houses, rough saloons and gambling houses— not the cozy and affordable places we now know and love.

‘Vilest Holes in the City’

By the 1870s, it was estimated by newspapers that there were “hundreds of saloons and dives where people were shot and stabbed,” although they sometimes used covers like cigar stores, boarding houses and hotels as decoys.

A letter to the editor in the Tribune recalled dives as places where men are “enticed, drugged and robbed.” A stretch of dives on Clark Street was among “the vilest holes in the city,” according to news reports.

Among the frequent perpetrators of bar violence at this time were sailors who came to port in Chicago, according to reports.

“Many of them have been loungers at the saloons and low dives, getting rid of their summer’s savings with a prodigal hand, or knifing each other in drunken brawls,” according to the Tribune. “A dangerous and toilsome life is theirs, and it is not to be wondered at that their moral sensibilities are blunted.”

Cracking Down

The early 1870s brought a new wave of efforts to try and control the dives .

In 1872, the city enacted a Sunday closing ordinance for drinking establishments, though bars unsurprisingly didn’t play along. Top police brass made promises to pursue the pubs as much as the law would allow, much to the annoyance of the divekeepers.

In March 1873, the Board of Police Commissioners attempted to limit the hours when saloons could operate, largely because of the crime associated with dives from 11 p.m.-5 a.m. By June, it was clear the no-booze Sunday laws weren’t working, and aldermen began to propose alternatives, like allowing them to sell wine and lager beer until 1 p.m. since it seemed they were doing it anyway.

Some rules limiting Sunday alcohol sales stayed in place until 2019.

In defiance of the growing Temperance movement, dives were known to employ women to attract customers by dressing up as religious anti-booze singers, a “simply infamous” tactic “intended to satirize the Anti-Rum movement,” according to an 1874 Tribune story .

By 1877, the “variety saloons” — dives that provided entertainment and alcohol — were the next target.

An April Tribune story from that year referenced how deplorable the dives were.

“The basement dives, as much wine-room as theatre … were the objectionable places,” the story said. “They should be killed out, and that on short order.”

The police chief agreed, reiterating that “they have got to shut up shop.”

“The city will soon be rid of such dives,” the article concluded.

By May, the variety saloon owners were asking the mayor to be allowed to once again sell liquor during its performances, “to relieve the thirsty audiences … from leaving their seats to ‘beer up,’” according to a newspaper report . The mayor said he would consider it.

But a year later, the issue of entertainment and alcohol, particularly in dives, was still being fought . An edict was made to stop “concert-saloons” from having music and booze at the same time.

Violent Reputation

While there was plenty of raucous buffoonery happening in the dives, there was also a lot of violence. In 1880, people would hit one another over the head with glass bottles, Wild-West style.

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Reports of stabbings, fights, shootings, druggings, robberies, stranglings and other general clobbering filled the papers, along with stories of young girls and women who had become involved in sex work at the dives.

An April 1881 article from the Tribune reported there were 43 licensed saloons on the west side of the street between Van Buren and Taylor considered by the newspaper to be dives, with a few German saloons between “these hell-holes.” The number of dives on Clark Street “is at least equally large” the newspaper said, estimating “that there are over 500 saloons in Chicago which do not deserve to be called respectable, and the closing of which would give satisfaction to every” respectable citizen and saloonkeeper.

The story stated that the previous Mayor Monroe Heath had “cleansed” Clark and LaSalle streets by revoking and never restoring licenses of the “concert dives,” which they claimed were now “flourishing” as legitimate venues while criticizing the current Mayor Carter Harrison.

Still, like in New York, dives were places where dark things could happen. In August of 1882 , police were visiting “several basement dives where the ‘pipe can be hit’” referring to “opium dens.”

Later, in November of 1899 , four Downtown dive keepers and proprietors of “notorious basement saloons” were indicted by a grand jury and charged with keeping disorderly houses due to women committing robberies “by the wholesale.”

Dives ‘Lead To Hell’

In 1893, Mayor Carter Harrison Sr. died. Several years later, in 1897, his son Carter Harrison Jr. was elected mayor. Supposedly, his administration was deeply engrained in the dive business.

In 1898, “Dives Defy The Law” appeared as a headline in The Inter Ocean newspaper for a story that recalled a reverend accusing the police of protecting dives and allowing them to thrive.

“Dives in Chicago have all the protection they need and want from the present city administration,” Rev. J.Q.A. Henry told a room full of mostly men while speaking at Willard Hall at Northwestern University. “The police officers of Chicago, generally speaking, are criminally guilty. They stand in the doorways of hell and prevent law-abiding citizens from enforcing the laws.”

Henry said he’d been doing his own investigations of these places and collecting evidence.

“When I speak of the front door to hell, I mean the doors, front, side, and rear, of the 6,300 saloons in Chicago,” he added. “They lead to hell.”

If strung out, the number of dives “would make a passageway into the infernal regions 31 miles in length,” he insisted.

According to Henry’s estimation, there were 10 saloons for every church and 20 barkeepers for every minister.

“Every year in this city enough liquor is consumed to float the battle-ship Illinois in a tank as deep as the Masonic temple is tall and as wide as an entire block,” he said, repudiating the “damnable dives.”

“If I had the power this very day I would close up every saloon dive, every gambling resort, every disorderly house, and we could once again look upon our city with pride,” the reverend proclaimed.

The priest said he had evidence against 100 “all-night” saloons, three of which were owned by aldermen. Henry promised he would go after politicians and dive owners after the next election, adding that some of the evidence was “the hottest stuff you ever heard.”

“Once we begin, convictions of hundreds of these divekeepers is certain,” he announced.

Although the mayor issued an order for all saloons on North Clark Street to close at midnight , “Those who know the ways of the street can get a drink at any hour,” according to the newspaper. Patrons and barkeepers were ignoring the rule and people were often seen coming out of “basement dives” at 12:30-1 a.m., despite the dive’s efforts to turn the lights down and keep its doors locked.

A common perception in the media was that the new Mayor Harrison was soft on dives — even congenial. Accusations of corruption between local politicians, city officials, police and dive owners were rampant.

An 1899 newspaper reported that Harrison and other officials had brought in an “army of illegal voters” into the city who were being bribed to vote for his slate and in the meantime were being housed in basement dives.

“From the administration’s saloon at No. 289 Clark Street a gang of thieves who were released from the bridewell yesterday was sent to the panel-house Democracy’s headquarters in the basement at No. 269 Clark Street,” The Inter Ocean reported . “This low-ceilinged, ill-ventilated cellar was crowded to the doors last night. … Thieves whose faces are familiar around the administration’s saloons and in the rogues’ galleries mingled with the vagabonds and drank from the pails of beer obtained from nearby saloons with money from the Harrison … corruption fund.”

That same year, another article alleged the Harrison administration planned to extort money from “dens of vice.” The story included a list of sums the “divekeepers and criminals” would have to pay, including $2,000 from basement dives and “fences” in the 1st Ward and $10,000 from basement dives, panel houses, petty criminals and “fences” from other wards. In addition to the gambling rooms, poolrooms, disorderly houses and more, about $151,000 in “blackmail” money was to be raised by the new levy, according to The Inter Ocean .

An estimate from The Inter Ocean that year placed at least 150 all-night dives across the city.

In December of 1900 , an article with the headlines, “Will Let Dives Remain,” and, “Mayor Says Vice Always Existed; Won’t Check It Now,” Mayor Harrison said no license would be revoked “simply because a resort is one of bad repute” — so long as there aren’t robberies and that they obey a midnight closing ordinance. In the same article, the mayor was defiant in his position that he had cleaned up disreputable saloons over the years and hadn’t received enough credit for it.

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That same month, a religious crusade against basement dives, gambling and other vices was becoming more and more prevalent, with much blame laid on the mayor.

Just before the end of the year, a news article reported that “Mayor Harrison experienced an eleventh-hour change of heart for political purposes toward the basement dive saloons yesterday.”

Right as the work day was ending, he called reporters to City Hall and told them he investigated the dives “and had learned that they were against the morals of the city.” He revoked the license of seven basement saloons.

However, the barkeepers supposedly received a “tip” earlier in the day that their saloons would be closed, but that after a few days, “the mayor would put up a weak fight and the licenses would be restored by order of the court.”

Investigating The Dives … And City Hall

Before the end of 1900, a grand jury convened to discuss cases regarding all-night saloons and basement dives.

On December 19, the jury voted unanimously to make a thorough investigation of “City Hall scandals” — including police officers being paid “hush money” by basement dives. The investigation would include “an inquiry as to the operation of basement dives, other places of disrepute, and all-night saloons” and looking into the allegations “that a clique of [police]men standing close to the City Hall powers demanded money from applicants for places on the police on the police force,” according to the Tribune .

As the investigation was underway, the theme of corruption and dives continued in the public discourse.

“One crooked county contractor robs the people of more in a day than the ‘basement dives’ do in ten years,” wrote the Chicago Eagle . “And yet the county contractors are not investigated.”

In 1901, as the clamp on Downtown dives tightened, many of its frequenters went south , particularly many of the women who worked in the sex trade.

Still, the Downtown dives conducted business with the possible help of some palm-greasing, according to news reports. Both the Tribune and The Inter Ocean ran stories commenting on Mayor Harrison’s charges of bribery.

The ‘Wineroom’ Ordinance

Dives were frequently used as a political issue.

In 1901, a “wineroom” ordinance was being considered, which would forbid saloons from operating within 250 feet of a school, among other measures.

Winerooms were small areas, typically in dives, partitioned off so that only a few people could fit into them at once. They often had locked doors and a few small furniture items, like a table and chairs or a bed. Women often led men, usually drunk or drinking, into these rooms with the allure of sex, where they would typically attempt to rob them.

The ordinance was spurred by the death of a Hyde Park girl who had died after a night out at The Calumet bar at Cottage Grove near 38th Street. Curiously, it would also repeal the midnight closure rule for saloons.

“I included its repeal in my anti-wineroom ordinance because I hate hypocrisy,” blind alderman William Kent said. “I can’t see a foot, but there is no portion of this town that I can’t go to and find a saloon open between midnight and 5 o’clock in the morning.”

The ordinance was criticized for doing little to actually suppress “winerooms,” opponents said. Plus, the mayor and police chief already had the power to do what the law stipulated, some argued.

The ordinance prohibited the existence of private rooms in saloons shut off from public view by curtains, doors, screens, or any other device. Restaurants also couldn’t have private dining rooms where less than four people could dine in at a time unless they were all the same sex. Penalties ranged between $10-100 and revocation of a liquor license.

In December 1901, Mayor Harrison signed the ordinance. But the public wasn’t convinced.

Soon after, 600 saloon keepers (of 700 in the ward) had “begun a war which may lead to the political obliteration” of 1st Ward Alderman Michael Kenna, aka “Hinky Dink,” the newspaper reported.

The first person to be arrested under the new ordinance was Thomas O’Brien, who ran a saloon at 655 N. Clark St. (approximately 1552 N. Clark St. today).

Bars started calling their private dining and drinking rooms “storerooms,” kitchens, bedrooms and offices — sometimes legitimately converting them and other times not. But the chief of police said they needed to fully rid of them or risk losing their license altogether.

A New Era

Harrison Jr.’s first mayoral run came to an end in 1905. For years the city fought, sometimes toughly, sometimes half-heartedly, against basement dives, saloons and wine rooms.

By now, the Wild West-style saloon days were fading, replaced by a new kind of moral panic.

A 1907 August article in the Tribune described a Downtown bar called Silver’s “Rialto” at Randolph and Clark, run by George Silver, known to operate all-night bars, as akin to a red-light district.

“The atmosphere of the place, the pictures on the walls, the appointments, the music and particularly the clientele, suggest the red light district and lead the passerby and the casual visitor to wonder whether the days of the downtown basement dive have returned,” the story said.

From the street, you could hear ragtime music downstairs, as well as the mingling of men’s and women’s voices singing before the sound of applause and laughter. The place was described as having a long bar in a narrow room with photos on the walls and above the counter of actors, jockeys, boxers and “high art.”

Sound familiar?

Further down, South State Street was known as “Whisky Row,” a region now showing burlesque shows — exhibitions thought then to be of the most “extreme depravity.”

Before World War I, saloons were also billed as dance halls where women would usually perform for men, who would buy drinks, gamble and get free food with the purchase of booze, according to the University of Chicago’s exhibit, “ Something’s Brewing: The Art, Science and Technology of Beer Brewing .”

Still, “winerooms” were considered the “most viscous form of vice Chicago was ever cursed with” the Tribune reported .

“From the outside they looked like respectable saloons,” the paper wrote. “It was only when the stranger got inside he discovered the difference.”

In November of 1911, Police Inspector “Nick” Hunt said he would ban all women from saloons and make the Downtown district “like a Sunday school.”

By 1916, serious talk of Prohibition was beginning to scare brewers in Chicago, who placed an ad in an August edition of the Tribune with the title, “If Chicago Went Dry!” intending to show the far-reaching consequences of such a ban.

The following year, while basement dives still existed, they were no longer the scourge of the city they once were. New evils had emerged , like cabaret.

Prohibition-1950s

In 1919, the Volstead Act, also known as the National Prohibition Act, was introduced. The law aimed to enforce the 18th Amendment, which forbade the sale, production and transport of liquor that had 0.5 percent or greater of alcohol by volume. On January 17, 1920, the amendment was ratified to include the anti-alcohol Volstead Act.

However, the law failed to outlaw one aspect — the drinking.

In the 1920s, basement bars and hidden saloons became speakeasies where beer, wine and liquor reserves were kept for sale and consumption..

During Prohibition, 1920-1933, bars were officially shut down though many continued to operate secretly — reverting somewhat back to the illegal basement-style operations of the 1800s. Once again, illicit activities and unsavory characters hid their deeds below ground.

And so began the infamous era of mobster bootlegging, headed by crime bosses like Al Capone, Jonny Torrio, Dion O’Banion, George “Bugs” Moran and Frank Nitti, according to Chicago Crime Tours . Mob organizations, like Torrio and Capone’s “the Outfit,” claimed territories throughout the city and suburbs where they competed — often to the death — for control over the extremely profitable alcohol industry. According to estimates , Capone earned as much as $60 to 100 million dollars a year from his bootleg, speakeasy, gambling and prostitution businesses — over a billion dollars today.

While initially the gangs engaged in some profit-sharing, by 1922 the agreement had turned sour and the “Beer Wars” began. At the end, nearly 500 mobsters would be dead, mainly from shootouts. For the next several years, groups traded retaliatory killings of top brass, and in 1929 the stunning St. Valentine’s Day Massacre occurred — all Prohibition-related fallout.

Though this era was meant to curb so-called negative societal behaviors associated with being intoxicated, it ultimately gave rise to one of Chicago’s darkest and most violent times when criminal enterprises ruled with an iron fist (and maybe some brass knuckles). Police and politicians were also known to be corrupted and in the pocket of Capone and others.

In 1931, Capone’s run came to an end when he was sentenced to 11 years in prison for tax evasion. Two years later in 1933, Prohibition was repealed, and Chicago’s mobsters were forced to pivot to other operations.

Once Prohibition was repealed, many of the speakeasies dropped the charade and became legit, with some long-time survivors finding a place on our list.

The term “basement dive” became almost obsolete.

In 1940, a Chicago Symphony Orchestra performance of “The Beer Barrel Polka” was described as having the “zest and zoom one would expect to find in an especially good basement dive,” and in 1954 it was noted that high schoolers were drinking in basement dives.

But bars no longer had to operate underground, and many neighborhood taverns, pubs, bars and breweries had long-emerged above street level.

While the mob may no longer rule the city’s alcohol supply, Chicagoans are doing just fine drinking on their own — according to city data, there are 770 establishments that hold a tavern license .

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