Price$$$$
NeighbourhoodWest Loop
Hours{'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'}

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.

Location

Address: 955 W Fulton Market, Chicago, IL 60607

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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.

1520 N Damen Ave, Chicago, IL 60622

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.

12 S Michigan Ave, Chicago, IL 60603

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.

601 N State St, Chicago, IL 60654

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.

3349 N Halsted St, Chicago, IL 60657

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.

3356 N Halsted St, Chicago, IL 60657

Charlie's Chicago ★ 4.4

$$Wrigleyville / Lakeview{'monday': '15:00-04:00', 'tuesday': '15:00-04:00', 'wednesday': '15:00-04:00', 'thursday': '15:00-04:00', 'friday': '15:00-04:00', 'saturday': '15:00-05:00', 'sunday': '15:00-04:00'}

Charlie's on Broadway is the Chicago country and western gay bar opened 1993. Line dancing lessons run nightly from 21:00 before the floor switches to dance music at midnight.

Tip: Line dancing nightly from 21:00, lessons most weekdays before that. Saturday runs to 05:00, the latest in Northalsted. No cover before 22:00.

3726 N Broadway St, Chicago, IL 60613

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