Chicago Bars from Red Booths to a Conversation Pit

4.7 (513)

Mon – Thu, 17:00 – 01:00 (+1); Fri – Sun, 15:00 – 01:00 (+1)

2125 W Division St, Chicago, IL 60622, United States

Queen Mary Tavern reopened in 2015 after its Ukrainian Village saloon sat untouched for forty years. The narrow room channels English merchant and naval traditions. Its menu pairs maritime spirits, fortified wines and martinis with oysters and boquerones. The tavern takes no reservations.

4.6 (387)

Mon – Fri, Sun, 16:00 – 02:00 (+1); Sat, 16:00 – 03:00 (+1)

1150 N Damen Ave

Rainbo Club opened in 1936 and inspired the Tug & Maul Bar in Nelson Algren's novel The Man With the Golden Arm. Knotty pine, four red booths and eclectic art frame the room's vintage photo booth. Beers are listed on the walls. The bar is 21+ and cash only.

4.8 (140)

Tue – Wed, 16:00 – 00:00 (+1); Thu – Sat, 16:00 – 01:00 (+1); Sun, 14:00 – 20:00

2027 W North Ave

Clara pairs craft cocktails with live music in Wicker Park. Performances range from jazz combos and funk bands to classical string quartets and occasional tap dancing. The bar also serves mocktails, natural wine and small bites. Guests need to be 21 or older.

2500 W Chicago Ave

Dorothy occupies a former Ukrainian sports bar beneath Split Rail in Ukrainian Village. The lesbian cocktail lounge combines retro 1970s furniture with real candles and burnt amber furnishings. Settle into the conversation pit or take a place at the vintage bar top. Entry is 21+.