Secret Bars and Speakeasies in the Chicago Loop

Chicago’s history as a town filled with speakeasies and secret bars was formed during Prohibition. Al Capone and his gangster friends provided hooch for these hidden dens, making sure the city never went dry.

It may not be necessary to hide your adult beverage consumption anymore, but that doesn’t make it any less fun to have some cocktails in spots that are either hidden or evoke the romance of the 20s. We’ve found the best secret bars and speakeasies near the Loop and downtown Chicago (but don’t tell anyone).

The Drifter

Green Door Tavern is one of the oldest bars in the city in the only wooden building erected in River North after the Great Chicago Fire. After you enter the front door, which leans due to settling over the years, you head to the back and take the stairs down to The Drifter. You can’t get much more authentic; the basement bar was an actual speakeasy. With burlesque shows and era-authentic cocktails, you’ll feel like you’ve stepped backward in time with each step down to this subterranean bar.

Head to The Library and study our cocktail menu #cheers #giltypleasures

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Gilt Bar

A trip to The Library will be an education in craft cocktails. Located below Gilt Bar, shelves are lined with tomes and you can sink into plush banquettes while sipping on that perfect Manhattan under crystal chandeliers. Getting there may be a challenge, as the door is hidden. Make it easy on yourself by making reservations, and the host staff will personally guide you.

Sushi Dokku

For something completely different, look for the red arrow behind Sushi Dokku. This will take you to the Booze Bar, a Japanese spin on the speakeasy with street food, Izakaya-style small plates, and spinning vinyl. They’ve also got red and white wine on draft, as well as chilled sake.

Milk Room

Speakeasies are expected to be intimate, but the Milk Room takes it to a whole new level. Situated on the second floor of the Chicago Athletic Association Hotel, this micro-bar seats just eight people. You have to make reservations with a $50 deposit just to get in the door, but once you’re there you can indulge in cocktails made with extremely rare, vintage spirits and hard to find ingredients.

For a truly inside-scoop experience, visit one of these four secret bars and speakeasies in the Loop and downtown Chicago. Want to know of more cool spots? Follow us on Twitter and Facebook for all of the updates!

Author: Theresa Carter

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