Directory / Illinois / Chicago
Speakeasies in Chicago, IL
13 rooms worth the walk, from prohibition original, hidden door, hotel bar, jazz room, tiki lounge.
4.6Green Mill Cocktail Lounge
Uptown · Chicago, IL
Capone's favorite booth is still there, and so is the trapdoor story. Ninety years of jazz have not dimmed the green neon.
4.6The Violet Hour
Wicker Park · Chicago, IL
Behind a plywood mural on Damen: high-backed blue chairs, chandeliers, no cell phones, and the drink that taught the Midwest about mint and rose.
4.5Milk Room
The Loop · Chicago, IL
Eight seats in a room that sold milk during Prohibition, now pouring bottles older than the building's current name.
4.6Andy's Jazz Club
River North · Chicago, IL
A former newspapermen's tavern that has run live jazz since the fifties — three sets a night, no attitude.
4.6Lost Lake
Logan Square · Chicago, IL
Banana-leaf wallpaper, forty pages of rum, and the best-run tiki bar in the country wedged into a Logan Square corner.
4.6Three Dots and a Dash
River North · Chicago, IL
An alley of glowing skulls leads down to the loudest, most generous rum room in the Midwest.
4.5Billy Sunday
Logan Square · Chicago, IL
Named for the evangelist who once tried to dry out Chicago, this bar answers with a menu built almost entirely around amari and vermouth.
4.5Room 13
Logan Square · Chicago, IL
A hotel basement done up as a Prohibition club, complete with a barber-chair corner and drinks that take their time.
4.5Scofflaw
Logan Square · Chicago, IL
Named for the word coined during Prohibition to shame liquor-law breakers, this gin-forward bar wears the insult proudly.
4.5The Berkshire Room
River North · Chicago, IL
Leather wingbacks, a smoking-jacket mood, and a Dealer's Choice card that lets you order by adjective.
4.4The Drifter
River North · Chicago, IL
A former Prohibition-era hideaway beneath a River North tavern, where the menu is a deck of tarot cards and the cabaret runs between rounds.
4.4The Sportsman's Club
Wicker Park · Chicago, IL
A second-floor room above a taco counter, styled like a hunting lodge and pouring punches instead of the usual stirred-and-shaken lineup.
4.3Potter's Lounge
The Loop · Chicago, IL
Drinks beneath a ceiling fresco in the lobby of the oldest continuously operating hotel in America.