Chicago's best speakeasies
This essentially invitation-only bar (you can get rather pricey reservations through Tock) is a cozy 14-seat basement room decorated with antiques, framed paintings and sporting $20 cocktails. If you're lucky, your server upstairs at the Aviary may invite you to step through the locked door.
The Milk Room is located in the hallway between the Drawing Room and Game Room in what was formerly a speakeasy in the Chicago Athletic Association. To drink at this eight-seat bar, you'll need to purchase $50 tickets which will be applied to your bill.
The Green Door Tavern used to be patronized by Chicago gangsters, taking its name from the discreet entrance on the side of the building. If you walk down the metal staircase leading to the bathrooms—you’ll notice a door to a room that housed a speakeasy in the ’20s. That's the entrance to The Drifter, a craft cocktail bar with live entertainment and some stunning decor.
You won't see any signs for Violet Hour, only a long line of people waiting outside of an ever-changing, abstractly painted building. Enjoy pristine, thoughtfully crafted cocktails in towering modern-style thrones at this Wicker Park staple.
Find this '70s-themed bar hidden in the basement of Thalia Hall, which is decorated to look like place where your grandfather might have realxed. The drinks here are meant to be shared so grab a group of friends and order a colorful punch bowl.
Downstairs from the Gilt Bar you'll find a dimly lit room with red velvet booths and stacks of old books. The Library will make you feel like you've escaped to you're own secret club. Order top-notch classic cocktails or pick something off Gilt Bar's full menu.
This members-only club is located beneath The Old Chicago Inn. Entrance into this prohibition-era style bar requires a membership, an ever-changing password and proper attire. If you come as a member's guest then you'll be able to enjoy live jazz and 1920's inspired cocktails.
Enter the Double Door and find the staircase downstairs to the neon-glowing Door No. 3. This underground music club features acts ranging from indie rappers to drag performers.
Turn down the alley and arrive at a door that's really more of a strange wormhole, leading to a tiki bar in the middle of River North. Island-themed cocktails like Mai-Tais and daiquiris are served in cococut and tiki-head glasses.
This Japanese hideaway is tucked beneath sushiDOKKU, and you'll have to enter through the back alley door. In this dimly lit bar, guest can enjoy small dishes, Japanese snacks and Japanese draft beer, plus local favorites as well.
Hunker down in this underground space with live blues, eccentric art and craft cocktails. Enter this speakeasy music lounge through the nondescript alley.
The Pub is a longtime hangout at the University of Chicago with bar games, pub grub, cocktails and a rotating beer list. Unless you're a student or affiliated with the university, you'll have to tag along with a member to get access.
This underground lounge is enormous, the 18,000-square-foot space broken up into a labyrinthine set of handsomely designed rooms designated for cocktailing and live entertainment by swing orchestras and rockabilly outfits.