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.
Tip: Open daily from 17:00, weekends until 01:00. Sunset window books fast; weeknights walk in easy and the inside lounge stays open in winter.
Address: 2018 W North Ave, Chicago, IL 60647
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.
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.
Tip: Tock 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 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 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 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 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 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.