The Office ★ 4.8
$$$$West Loop{'monday': 'closed', 'tuesday': '17:00-00:00', 'wednesday': '17:00-00:00', 'thursday': '17:00-00:00', 'friday': '17:00-01:00', 'saturday': '16:30-01:00', 'sunday': 'closed'}
The Office in Chicago is the 21-seat speakeasy beneath The Aviary, hidden behind an unmarked door with vintage spirits, Persian rugs and one bartender per night.
Tip: Reservations through Tock only. The vintage spirits list goes deep; tell the bartender what era or distillery you want and they pull the bottle.
The Violet Hour ★ 4.7
$$$Wicker Park / Bucktown{'monday': '17:00-01:00', 'tuesday': '17:00-01:00', 'wednesday': '17:00-01:00', 'thursday': '17:00-01:00', 'friday': '17:00-01:00', 'saturday': '17:00-01:00', 'sunday': '17:00-01:00'}
The Violet Hour in Chicago hides behind a rotating mural on Damen Avenue. The James Beard winning pre-Prohibition room opened 2007 with curtained salons and a marble bar.
Tip: No reservations, walk in. The line out front moves; once you are inside the rule is no cell phones and conversations stay below the music.
Milk Room ★ 4.7
$$$$The Loop{'monday': '17:00-21:00', 'tuesday': '17:00-21:00', 'wednesday': '17:00-23:00', 'thursday': '17:00-23:00', 'friday': '17:00-23:00', 'saturday': '17:00-23:00', 'sunday': '17:00-21:00'}
Milk Room in Chicago is the eight-seat micro bar above Cindy's at the Chicago Athletic Association, pouring rare vintage spirits curated by Land and Sea director Paul McGee.
Tip: Tock reservations only. Sunday through Tuesday close at 21:00, Wednesday through Saturday at 23:00. Eight seats, no walk-ins.
Watershed ★ 4.3
$$River North{'monday': 'closed', 'tuesday': '17:00-00:00', 'wednesday': '17:00-00:00', 'thursday': '17:00-01:00', 'friday': '17:00-02:00', 'saturday': '17:00-02:00', 'sunday': 'closed'}
Watershed in Chicago tucks beneath Pops for Champagne at State and Ohio. A staircase marked with a large W drops to a basement of stone walls and seasonal cocktails.
Tip: Walk-in only, no reservations. The cocktail menu rotates by season; ask the bartender about the rotating themed list pulled from TV shows.
Sidetrack ★ 4.7
$$Wrigleyville / Lakeview{'monday': '15:00-02:00', 'tuesday': '15:00-02:00', 'wednesday': '15:00-02:00', 'thursday': '15:00-02:00', 'friday': '15:00-02:00', 'saturday': '13:00-03:00', 'sunday': '12:00-02:00'}
Sidetrack on North Halsted opened 1982 as the Northalsted video bar with six rooms, a rooftop deck and themed video nights from Show Tunes Monday to Musicals Sunday.
Tip: Show Tunes Monday and Musicals Sunday are tradition; no cover any night. The rooftop is the warm-weather spot, the Glass Bar handles overflow.
Roscoe's Tavern ★ 4.5
$$Wrigleyville / Lakeview{'monday': '15:00-02:00', 'tuesday': '15:00-02:00', 'wednesday': '15:00-02:00', 'thursday': '15:00-02:00', 'friday': '15:00-02:00', 'saturday': '12:00-03:00', 'sunday': '12:00-02:00'}
Roscoe's Tavern in Chicago has anchored Halsted Street since 1987 with a pool table room, fireside chat area, sidewalk patio and a dance floor that runs late on weekends.
Tip: No cover before 22:00 most nights. Saturday closes at 03:00, the latest in Northalsted. Drag bingo and trivia rotate through the weekday calendar.