- The Berkshire Room: 15 E Ohio St. Tucked within the also-historic Acme Hotel, the Berkshire Room is an authentic speakeasy with premiere cocktails and old-school atmosphere. Look at the walls for faded signs from over 100 years ago when it used to be a Japanese-themed bar called the Tokyo Room!
- Sparrow: 12 W Elm St. Sparrow is a cozy spot hidden in the Gold Coast with a colorful history as a historic speakeasy underneath a mob owned hotel and brothel. With signature craft cocktails and elegant decor, Sparrow offers a perfect setting for friends or date night. It honestly is my favorite place to go with friends, my go-to is the Grasshopper.
- The Violet Hour: 1520 N Damen. The Violet Hour is accredited with being a leading figure in the cocktail renaissance we’ve seen over the last 15 years. The entrance is marked by an inconspicuous sign making for pure speakeasy charm.
- The Drifter: 676 N Orleans St. Don’t be mad at me for explaining this completely, but part of the joy is finding this place. 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 in the basement. 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.
- 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.
P.S, If you are looking for things to do in Chicago, please try our Chicago Murder Mystery Tour!