Video: Chicago Speakeasies: An Era of Secrecy and Celebration

Some Chicago Speakeasies Still Thriving Today

By Sonia Vavra, Sarah Basheer and Sean Barry

Posted: Saturday, Dec. 23, 2017

On Dec. 5, America celebrated a special anniversary -- the day we got our booze back.

On that day in 1933, the U.S. Congress ratified the 21st amendment which repealed the prohibition act of the 1920s and restored liquor nationwide. 

The 1920s was a rich and vibrant era in American history, politically, economically, and socially. It's best known for its thriving spirit and debauchery. The 1920s brought with it many illegal activities: prostitution, child labor and the buying and selling of alcohol.

Prohibition took place from 1920 until 1933, and Chicago was very much a part of that era of restriction. Anyone who has lived near or visited Chicago has at least heard of Al Capone and the old-school gangster involvement in the Prohibition era—but few know that many of the original Prohibition speakeasies from that time still exist today in the city's neighborhoods today.

“The idea of speakeasies, especially that’s in popular culture is where you would knock on a secret door and some big guy who’s a bouncer would slide open a little slot and just peer out, seeing his eyes only and then ask for the password and you would say whatever the password was and get let in,” said Peter Alter, a historian with The Chicago History Museum.


Map: Check out this interactive StoryMap for more historic locations wher you can grab a drink. 

Speakeasies were underground—figurative and sometimes literal—establishments where people went to drink alcohol illicitly during Prohibition. They were meant to be secretive and somewhat hidden from the public, namely law enforcement, but were not difficult to get into for many.

“Chicago had as many as 3,000 speakeasies which seems like a really crazy high number and I was a little bit surprised at how many that is or was," Alter said. "The population of Chicago in 1920 was probably actually not much smaller than it is now probably between 2 million and 2.5 million. So however many speakeasies that is per person, I think that’s a pretty high number.

“What typically happened to those kinds of places was that they were once restaurants, bars and saloons before and they went back to that or they now became legitimate businesses, or people gave them up because they no longer saw owning a former speakeasy to be as profitable as it once was."

Many of these speakeasies still exist in Chicago today, and are easier (and legal) to visit. Step into these old-fashioned bars and you can still feel the aura of the 20s and 30s—jazz, dancing, and an undeniable need to celebrate and socialize during a time of strict law enforcement in secrecy.

In honor of the upcoming anniversary of Prohibition and the subsequent birth of the legendary Chicago speakeasies, here is a list of some of the best locations that helped pave way for Chicago’s modern-day bar scene, some of which have stood the test of time:


 (Photo courtesy The Green Door Tavern)

The Green Door Tavern

678 N Orleans St, Chicago IL 60654

The Green Door Tavern serves as more than one aspect of Chicago history. The structure itself was built in 1872 and has undergone several renovations and refurbishments, but the original wooden facets are still intact.

“In 1873, Chicago passed an ordinance that no wooden structures could be built, this was after the Chicago Fire, so this place is only one of three or four buildings that are still wooden.”

This establishment has a long history.

“It was actually initially a grocery store,” said one of the managers, Buddy Heely.

He also mentioned how it has changed ownership many times before finally becoming a small tavern. In 1921, Vito Giacomo opened a restaurant and named it The Green Door Tavern in the heart of Prohibition.

“I don’t actually know what that means, the definition of a tavern, maybe it was more of a public house or something like that,” Heely said.

Read: Interactive timeline of the history of Prohibition

The name may give homage to the Prohibition era tactic of painting a door green to indicate a speakeasy within. The owners of The Green Door Tavern continue to celebrate the legacy of this institution.

“Just in 2015, the beginning of 2015, we opened up the speakeasy for everyone to come in from Wednesdays to Saturday,” Heely said.

The basement speakeasy is a modern rendition of the famed rooms used to illegally sell and consume alcohol during the 1920s and many of the furnishings are still from the restaurant’s initial opening in 1921. 

“It’s a really great place to come visit and get the experience because it’s a wooden structure and it’s got a lean,” Heely said.


The Gold Star Bar in Chicago was popular among Polish immigrants during Prohibition. (Photo/Sonia Vavra)

Gold Star Bar

1755 W Division St, Chicago IL, 60622

What now exists as a trendy area for IPA-drinking hipsters and bike-riding yuppies, Division Street in modern-day Wicker Park used to be a hot area for speakeasies. A hole-in-the-wall bar, Gold Star falls on the side of a cozy, welcoming environment, not without a touch of the Prohibition-era mystery.

“The building was built in the 1870s. It’s definitely a Prohibition bar, [it] opened around the 20s sometime. There used to be 23 rooms for rent upstairs, it was kind of like a boarding house [or] brothel,” said Gold Star Bar manager Dave Cartwright.

Around that time, Division Street became a place inhabited by Polish immigrants. Outside hangs an old-fashioned neon sign reading Gold Star Lounge, which remains there from the Prohibition days in which the upper part of the building also served as a “hotel.” 

The Gold Star has stood the test of time from economic decline to gentrification, and even to a few visiting ghosts here and there. That’s right — the Gold Star Bar is rumored to be haunted. In the height of the gangster era in Chicago, it is reported that a former bartender shot and killed a man that had the intentions of robbing the bar.

Interior of Gold Star Bar (Photo/Sonia Vavra)

“There have been quite a few people who have died, obviously because the building has been around for a while," Cartwright said. "There [are] bullet holes in the brick glass out front, those are also original. That guy died in the front door … I wish I’ve seen a ghost, but I haven’t. Although the jukebox does randomly turn on at a very loud volume.” 

As for its contribution to the bar scene during Prohibition, the Gold Star Bar speaks for itself.

“Because it’s one of the oldest bars in the city, it’s definitely a destination, a landmark, and it was its own entity on Division Street.," Cartwright said. "It was a secret watering hole for people to cut loose.” 

The Green Mill

4802 N Broadway St, Chicago IL, 60640

The Green Mill cocktail lounge is one of the most notorious bar and jazz lounges in Chicago. With a unique taste in both casual and upscale, the Green Mill has an enticing aura to it that beckons for visitors to return for the music, drinks, and dancing again and again.

One of these regulars in the days of Prohibition was Al Capone, the famous gangster himself. Capone was a respected member of the Green Mill, and even had his own booth where he could see both the front and back entrances when seated.


 WWI dated photo of the Green Mill Lounge (Photo/Sean Barry)


The Green Mill even has a secret passageway behind the bar—used to smuggle in the illicit alcohol, as well as a quick and easy exit for Capone had there been a debacle between him and any gang members that might be coming for him.

Upon entering the Green Mill Lounge, it is hard to remember what year it is. The bar has a faint musty smell to it similar to the one in the basement of your grandparent’s house and the original clamshell light fixtures on the ceiling provide the perfect amount of dim lighting like a jazz club in a movie.

The Uptown bar opened in 1907 and was originally called Pop Morse’s Roadhouse.

“The only thing in the neighborhood at that time, was the cemetery,” said Jason Cole, a 20 year employee of The Green Mill Lounge and current manager. “Pop Morse’s Roadhouse catered mostly to groups leaving funerals.”

Cole added that in 1910, it was bought out by the Chamales brothers, who converted it into the Green Mill Gardens, named after the famed Moulin Rouge in Paris. Green Mill Gardens was a dance hall and beer garden that stretched the entire city block. Green Mill Gardens was a high-society establishment during that time with regulars like Hollywood legend, Charlie Chaplin.

“Before McGurn took over the bar, a lady named Texas Guinan, use to run the bar. This was early during prohibition and she had a famous line, ‘I don’t sell drinks. I just rent glasses,’” Cole said.

Texas Guinan was an actress and entrepreneur who made her film debut in “The Wildcat,” in 1917. There’s even an article from The New York Times on March 23, 1930, that details a shooting that took place at the Green Mill Gardens involving Guinan. Cole even shared a recent picture that surfaced of the Green Mill from the prohibition era displaying a sign above the establishment claiming it was a jewelry store.

As years passed, Jack McGurn or “Machine Jack,” one of Capone’s well known associates, took part ownership of the bar.

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