Best-of list · Speakeasies
Chicago hides serious cocktails behind unmarked doors and basement stairs. Here are the 5 real speakeasies still open and worth finding in 2026.
The short answer
5 ranked rooms follow. How we picked is at the end of this guide.
Chicago has the deepest speakeasy bench in the country, but the scene took some hits. The Violet Hour and the Milk Room both closed for good, so they are off this list. What is left still makes you find an unmarked door or a basement stair.
We cut the open cocktail bars and tiki rooms that get filed under speakeasy and kept five that are genuinely hidden and genuinely still pouring. Here they are.
The Drifter hides in the basement under the Green Door Tavern at Orleans and Huron, in a room that ran as a real speakeasy during Prohibition. The menu is a deck of more than 100 tarot cards, and the bartenders pull a handful each night to set the list. Burlesque and live acts run late. It opens Wednesday to Saturday. Best for a group that wants a show with the cocktail.
Full listing & hours →The Office sits behind an unmarked door directly below The Aviary, Grant Achatz's cocktail lab in Fulton Market. The 21 seats book out fast, and the program leans on rare and vintage spirits with luxury bites to match. Reserve through Tock well ahead; walk-ins do not happen here. It runs Tuesday to Saturday. Best for a serious drinker who will pay for a pour they cannot get elsewhere.
Full listing & hours →Untitled Supper Club runs under Kinzie Street in River North, a Prohibition-style supper club with live jazz, burlesque, and one of the largest American whiskey lists anywhere. It is a big room that still keeps the below-street, after-hours feel. Music plays late, Tuesday to Saturday. Best for a long night with whiskey and a band, not a quiet two-top.
Watershed is the basement bar under Pops for Champagne at State and Ohio in River North. Each season the menu rebuilds around a different television show, which sounds gimmicky and drinks better than it should. The low brick room stays calm when the street above is packed. It opens Tuesday to Saturday. Best for a quiet, well-made cocktail a flight of stairs off the sidewalk.
Bordel hides on the second floor above Mama Delia on Division Street in Wicker Park, styled after the cabarets of Paris. Now past its tenth year, it runs burlesque and live jazz most nights, with two shows on the late end of the week. The drinks hold up to the spectacle. Best for a date that wants performance with the pour, not a quiet corner.