Few cities can so effortlessly merge history and the present-day into one intoxicating experience like Chicago can, especially when it comes to alcohol. Windy City mixologists certainly embrace the historical romance of the metropolis, and no time period stands out more than the 1920s, which introduced radical cultural changes and debauchery—think mobsters, Art Deco design, jazz, bobbed hairstyles, first-wave feminism, and, of course, Prohibition.
Now, modern-day speakeasies run rampant throughout the city paying homage to those bygone days. And while you won’t run into Al Capone, chances are you’ll feel like you’re stepping back into the riotous blur of the Roaring Twenties—if you know the entrance password.
Location: 955 W. Fulton Market
This dimly-lit lounge with just 14 seats is located beneath the exclusive bar The Aviary—and admittance into The Office is even more restrictive. Your best bet for getting in is by personal invitation from your server upstairs at The Aviary. You can also book an expensive reservation online. Once the locked door is opened for you, bask in your success in a distinguished room filled with art and antiques, and sip classic drinks made with top-dollar ingredients. All drinks are $20 each and made with a single spirit.
Location: 3222 N. Sheffield Ave.
Bartenders bring the Prohibition era to life with Jazz Age libations and cultural anecdotes in this speakeasy. The entrance is located in the alley to the left of the Old Chicago Inn on Sheffield and Belmont. Look for the red-lit gate with an “RM-13” logo and knock. A bartender will greet you at the door, but you’re not in yet. You’ll have to know the frequently-changing password. If you stay at the Chicago Inn, you’ll receive an invitation to the bar, or you can apply for a bar membership with a yearly fee. Otherwise, put your detective work to use in tracking down someone who may have the password and be kind enough to share. Formal attire is required, which means jackets for men, and absolutely no denim or athletic wear.
Location: 1721 W. Division St.
Inspired by a mashup of time periods—Paris’ Belle Époque and Chicago during the time of the Prohibition—this hidden craft cocktail bar features a rotating cast of jazz musicians, burlesque performers, magicians and cabaret dancers. Add eclectic interiors and era-appropriate alcohol to the entertainment, and you’re in for quite a show.
Location: 353 W. Hubbard St. Lower Level
Located in the River North neighborhood below The Hampton Social Restaurant, this live music cocktail lounge is inspired by the 1960s British Invasion. Note: That alleyway entrance you see isn’t actually for a tobacco shop like the sign says, but for this speakeasy. Once you enter through the deceptive door and into a world of Union Jacks, be immersed in the sounds of live music—jazz, R&B, throwback bands—while lounging jauntily on velvet and leather couches. Finally, take in the sights, sounds, and, of course, cocktails, old sport.
You can fly with WOW air to Chicago from all around Europe several times a week, all year round.
Words: Krista Connor
Photos: Courtesy of respective venues