The Up Room is a rooftop bar in Wicker Park / Bucktown, Chicago.
Editorially verified May 20, 2026 by Elliot Marsh, TableJourney editor. Source.
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.
Water activity · 1.5 hours
Climb aboard a 90 passenger historic riverboat & sip cocktails while cruising the Chicago River! Relax and learn about the history & architecture of the city via live ...
2 hours
Unleash your creativity with a fun paint and sip experience in Chicago. Enjoy a relaxed atmosphere with music, drinks, and plenty of laughs as you create your own masterpiece.
Guided tour · 2 hours
Discover Chicago's Ukrainian Village on a Mid-Century Cocktail Bar tour. Visit three hidden bars, enjoy craft cocktails & beers for you to purchase, and maybe experien...
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.
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.
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 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 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 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 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.
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.
TipNo cover before 22:00 most nights. Saturday closes at 03:00, the latest in Northalsted. Drag bingo and trivia rotate through the weekday calendar.
