Head to these five hotspots for great cocktails—and entertainment on the side.
Filled with pulp imagery and a whimsical edge—check out the risqué custom wallpaper—this Wicker Park lounge offers craft cocktails and live shows ranging from burlesque to jazz.
2. Smokey Hollow
This new River North spot channels a vintage vibe with retro design details while at the same time entertains with an eclectic mix of performers on its red-curtained stage.
3. The Drifter
A unique evening awaits for a carefulling crafted cocktail and something you don’t see every day—circus sideshow, anyone?—at this charming lounge located below the Green Door Tavern.
4. Coq d’Dor
This legendary Drake Hotel bar opened to a line of thirsty patrons after the repeal of Prohibition in 1933. It still draws plenty of loyal fans who appreciate the historic vibe, classic cocktails and live music.
5. Green Mill
Head to this Uptown lounge on Wednesdays and you’ll be awarded with the gypsy-swing sounds of Alfonso Ponticelli and Swing Gitan.