The Up Room ★ 4.3
$$$$
$18 cocktails, walk-in or OpenTableWicker Park / BucktownMon-Thu 17:00-00:00, Fri-Sat 17:00-01:00, Sun 17:00-00:00.
The Up Room crowns the 13th floor of The Robey, Wicker Park's tallest building, with a wraparound terrace facing the Loop skyline and the six-corners street.
TipOpen daily from 17:00, weekends until 01:00. Sunset window books fast; weeknights walk in easy and the inside lounge stays open in winter.
The Aviary ★ 4.7
$$$$
West LoopTue-Thu 17:00-00:00, Fri 17:00-01:00, Sat 16:30-01:00. Closed Mon/Sun.
The Aviary in Chicago opened 2011 as Grant Achatz's Alinea Group cocktail lab, applying fine-dining technique to a five-course tasting of cocktails paired with small plates.
TipTock reservations only, no walk-ins. The seasonal 5-course tasting is $145; sit at the bar to watch the kitchen build the drinks.
The Office ★ 4.8
$$$$
West LoopTue-Thu 17:00-00:00, Fri 17:00-01:00, Sat 16:30-01:00. Closed Mon/Sun.
The Office in Chicago is the 21-seat speakeasy beneath The Aviary, hidden behind an unmarked door with vintage spirits, Persian rugs and one bartender per night.
TipReservations through Tock only. The vintage spirits list goes deep; tell the bartender what era or distillery you want and they pull the bottle.
The Violet Hour ★ 4.7
$$$$
Wicker Park / BucktownDaily 17:00-01:00.
The Violet Hour in Chicago hides behind a rotating mural on Damen Avenue. The James Beard winning pre-Prohibition room opened 2007 with curtained salons and a marble bar.
TipNo reservations, walk in. The line out front moves; once you are inside the rule is no cell phones and conversations stay below the music.
Watershed ★ 4.3
$$$$
River NorthTue-Wed 17:00-00:00, Thu 17:00-01:00, Fri-Sat 17:00-02:00. Closed Mon/Sun.
Watershed in Chicago tucks beneath Pops for Champagne at State and Ohio. A staircase marked with a large W drops to a basement of stone walls and seasonal cocktails.
TipWalk-in only, no reservations. The cocktail menu rotates by season; ask the bartender about the rotating themed list pulled from TV shows.
Sidetrack ★ 4.7
$$$$
Wrigleyville / LakeviewMon-Fri 15:00-02:00, Sat 13:00-03:00, Sun 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.
TipShow Tunes Monday and Musicals Sunday are tradition; no cover any night. The rooftop is the warm-weather spot, the Glass Bar handles overflow.