5 of the Best Speakeasies in ChicagoAudrey Snyderon January 29, 2021 at 4:05 pm

Though legislation repealing Prohibition was ratified back in 1933, our cultural fascination with the Prohibition era (and with much of the mob activity that marked it) keeps us going back to basements and backrooms made to emulate that time in our history. Not only can one find a swanky, dimly-lit environment that evokes the shady underworld of Al Capone, but creative and delicious cocktails have also become a hallmark of the (sometimes) password-protected, contemporary speakeasies and Chicago’s are some of the best.

Three Dots and a Dash

435 N Clark St, Chicago IL 60654

Over a summertime weekend, the line for this tiki-style speakeasy can easily stretch down the alley outside. Luckily, the fruity concoctions are pretty fantastic and the bar bites are delicious, so it really is worth it to brave the line. Keep it classic with a Mai Tai, or try something new with the Trouble in Paradise: Japanese whiskey, toasted sesame, and Sirop de Canne.


The Violet Hour

1520 N Damen Ave, Chicago IL 60622


In trendy Wicker Park, you’ll find a “seasonally rotating cocktail list,” an impressive list of spirits, and an intimate drinking experience and The Violet Hour, whose drinkable creations have earned it the James Beard Award. Try the smoky Mezcal-based Witch Doctor, or a Blueridge Manhattan with a healthy dose of Rittenhouse Rye.

Milk Room

12 S Michigan Ave, Chicago IL 60603

This tiny bar that sits on the second floor of the Chicago Athletic Association accommodates just 8 chairs, serves up “spirit-forward” cocktails, and prides itself on using high-quality and hard-to-find ingredients.

Booze Box

823 W Randolph St Downstairs, Chicago IL 60607

From bright and fresh to dark and smoky, this basement bar living below sushiDOKKU offers cocktail flavors to interest every palate. Try the hot Atatamare Punch with Hendrick’s gin, yuzu, and matcha; or keep things cool with a Lychee Club (Roku gin, St. George raspberry, lychee, lemon, and egg white).

Janitor’s Closet

312 W Chestnut St, Chicago IL 60610

Located at the Fieldhouse Jones, this intimate space includes just 15 seats for its guests to experience intriguing craft cocktails, which include flavors from both around the world and close to home in the Midwest.

Speakeasies Chicago Featured Image Credit by billadelphias from Pixabay 

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