The Milk Room
8-seat bar inside the Chicago Athletic Association Hotel. The rarest spirits on the planet poured in a room that seats fewer people than most dinner tables. Reservation essential. Two-hour maximum.
Scofflaw
The city's definitive gin bar. 100+ gins. The bramble is the signature. No sign on the door until you know where to look. One of the bars that made Logan Square a destination.
The Drifter
Below the Green Door Tavern, through an unmarked door, is one of Chicago's most whimsical and genuinely excellent cocktail bars. The room is lit like a circus and the drinks are serious. Hidden in the most theatrical sense.
Delilah's
Punk rock bar operating since 1993 with 400 whiskeys, the best punk and metal jukebox in America, and zero tolerance for bad vibes. The staff know every regular by name. A Chicago institution that tourists walk past every day.
The Aviary Office
Grant Achatz's cocktail tasting experience. 12 seats. Reservation months ahead. The most ambitious cocktail experience in America. One of the few bars that justifies a trip to Chicago by itself.
Lost Lake
Chicago's finest tiki bar, tucked on a Logan Square side street with no advertising. The rum list has 200 expressions. The mai tai is the best in the Midwest.
Sportsman's Club
Back patio from April through October. Taxidermy, serious cocktails, and a genuinely hidden-feeling address in Ukrainian Village. One of the better secret patios in the city.
Soucie's Bar
Cash-only neighbourhood dive that Andersonville residents protect with fierce loyalty. No frills, $4 beers, and the kind of regular crowd that makes a bar worth visiting. Hard to find, worth finding.
Jackhammer
The Lakeview gay dive bar with arguably the best back patio in the neighbourhood. The crowd is welcoming to anyone who arrives with good intentions and cash.
Quenchers Saloon
200 beers, bar games, and a neighbourhood crowd that has been coming here since 1986. The beer menu is printed on a laminated sheet that changes weekly. No app, no QR code.
Hungry Brain
A music venue the size of a living room that also happens to pour great drinks. Sunday jazz at 9pm is a Chicago secret worth keeping.
Estelle's
The 4am bar for Wicker Park's bar industry workers when everything else closes. Opens at 4pm, closes at 5am. The staff take no nonsense and pour generously.
Lottie's Pub
Bucktown's oldest bar, operating since Prohibition. The shuffleboard table is the best in any Chicago bar. Cash only, no tourists, no attitude.