There’s a reason why speakeasies in Chicago have lasted more than 100 years after prohibition when they first emerged.
The Prohibition Era began in 1920 when the 18th Amendment to the U.S. Constitution banned the manufacture, transportation and sale of intoxicating liquors. The National Prohibition Act, or the Volstead Act, an intoxication was any beverage that contained more than 0.5 percent alcohol, according to United States archives.
However, prohibition was hard to enforce. The sale of liquor, known as “bootlegging,” and speakeasies, or illegal drinking locations, emerged rapidly. The 21st Amendment ratified the 18th Amendment on December 5, 1933, but speakeasies are still a phenomenon more than 100 years later.
Places where you used to provide a password to lay low and hide the consumption of alcohol from authorities, are now places where people who crave exclusivity and small intimate crowds are hanging out. There’s no better way to sip on history than Chicago, which has hosted some of the most prolific and notorious mobsters. You may not need a password anymore, but you need to have a watchful eye and sometimes a reservation for the best speakeasies in Chicago.
The Violet Hour
Located in the heart of Wicker Park, The Violet Hour is an iconic destination for cocktail enthusiasts.
Once inside, guests will enjoy a list of James Beard Award-winning prohibition-style cocktails that changes each season. Their drinks and bourbon menu are sought by tourists worldwide because they’re rare.
If you’ve been here before and can’t find it, note you’re not alone. The mural façade changes often to feature a different artist. All you have to do is find the doorknob hidden on the mural. Be on the lookout for some fun and creative cocktails brought to you by the speakeasy’s theme.
For June, the theme is Murder Mystery at The Violet Hour. There’s a clue-inspired menu that will help you find the killer after a fictional murder.
The Drifter
The Drifter is an authentic 20s-era speakeasy in the basement of the Green Door Tavern. Take it all in because as you enter, because out of all the speakeasies in Chicago, you’re stepping on the same floor where drifters have treaded for over 100 years.
The Drifter has a rotating menu of more than 100 cocktails on Tarot Cards. The team of bartenders chooses a handful of cards each night from the deck. If you’ve been here before, you never know what to expect for the evening. There are nightly live bands and burlesque performances.
If you want a taste of the unknown, you can ask your bartender for a fortune cookie surprise. For just $10, you will receive a fortune cookie, and the bartenders will make you whatever drink is inside.
The Office Room
This isn’t your regular office space. The Office Room is an upscale speakeasy beneath The Aviary cocktail bar. Think of it as a space away from Chicago’s bustling night scene.
It’s good to be tucked away from people because the bar offers rare vintage spirits and classically inspired cocktails you won’t find anywhere else in the city. It’s important to note that you should book a reservation at The Office Room. In addition to cocktails, you can reserve decadent food selections and a tasting menu.
The Library At Gilt
After eating at the Gilt Bar, head downstairs to finish the evening in a booth at The Library. It’s a lowlight and intimate speakeasy lined with books, flickering candles, velvet booths, vintage art and fringed chandeliers.
The Library at Gilt is in the basement through an anonymous side door. Go down the hallway lined with photos until you find the unmarked door to your right.
The Library is open Thursday from 6 p.m. to 10:30 p.m. and on Friday and Saturday from 6 p.m. to 11 p.m. Limited reservations for the Library are released every Wednesday for the week pending any private events. There’s also some room for walk-in guests.
Bordel
When the sunsets in Wicker Park, step inside Paris at Bordel. Bordel is a cocktail bar and cabaret that seductively channels the revelry and energy of Paris’ Pigalle and Montmartre.
Bordel is one of the sexiest speakeasies in The Windy City surrounded by vintage décor and candlelights.
Through the hidden door and up the leopard-print stairs, you will find yourself inside Bordel. There are pink velvet sofas and drapes, tasseled chandeliers, vintage bronze “cherub” sconces, Persian Bokhara hand-knotted rugs, and walls covered in custom, handcrafted wallpaper inspired by 20th-century American pulp cover artistry.
Topping off the ambiance on any given night is a cast of jazz musicians and burlesque performers. This speakeasy is one of the top destinations for discovering new talent and hearing high-profile DJs.
Bordel prides itself on being the originator of the “cocktail porrón.” It’s a playful blend of their Spanish roots, the team’s indulgent love of great drinks, and what they describe as their “oft-imitated world-famous Spanish coffee.”
The award-winning beverage team is led by industry vanguard Brian Sturgulewski, where they create unique “bordel-ed” twists on classic cocktails.
The Milk Room
If exclusivity is what you’re looking for, then this is the space for you. The Milk Room is a hidden eight-seat microbar that offers a spirit-forward cocktail menu crafted from some of the rarest vintage spirits and elixirs.
Consistently recognized as one of the top bars in Chicago, The Milk Room is located on the second floor of the Chicago Athletic Association. During the Prohibition Era, members of the exclusive athletic club would stop in for glasses of milk mixed with alcohol to avoid penalties from authorities.
With limited seating, reservations are required. Look for the ornate stained-glass doors on the second floor to find this hidden gem.
