- The Violet Hour: 1520 N Damen. The Violet Hour is accredited with being a leading figure in the cocktail renaissance over the last 15 years. The entrance is marked by an inconspicuous sign making for pure speakeasy charm.
- The Drifter: 676 N Orleans St. If you go to the marked address you will find yourself in the Green Door Tavern, one of the oldest and storied bars in Chicago, whose Green Door is a leftover symbol of the Prohibition Era. That’s great, but I said to go to the Drifter, which is a second bar hidden inside. I cannot tell you how to find it, but let’s just say not every wall is as it appears. Both watering holes are fantastic, but the Drifter’s cocktails are truly timeless.
- The Library: 230 W Kinzie. Once again, if you go to the marked address you will find Gilt Bar, an incredible restaurant and speakeasy inspired bar in its own right. To find the Library, you’ll need ot head to the basement, and make sure to bring your library card (I.D)!
- Untitled Supper Club: 111 W Kinzie. This imitation speakeasy boasts the largest whiskey library in the city with over 700 varieties. Come after 8 most nights for a live music and burlesque show. As the title suggests it’s discreetly hidden, but once you find your way in you may never want out.
- The Milk Room: 12 S. Michigan. I’m sorry to keep sending you to different places, but that’s what it takes to keep the feds out! 12 S. Michigan is the Chicago Athletic Association, a historic and charming hotel and gameroom that is the inspiration for the Chicago Cubs logo. To find the hidden booze however, ask around for the Milk Room. It’s an intimate 8-seat micro-bar that still has artifacts from when it served the highest members of society during the Prohibition era.
Happy hunting, and even happier drinking! Hope you enjoy some of the best bars in Chicago.