Cindy's rooftop in Chicago sits on the 13th floor of the Chicago Athletic Association with all-season terrace seating that frames Millennium Park and Lake Michigan.
Tip: Weekends fill from 21:00; reserve via OpenTable or arrive at 16:00 for the sunset window. The terrace stays heated and open year-round.
Address: 12 S Michigan Ave, Chicago, IL 60603
LH Rooftop in Chicago crowns LondonHouse on the corner of Wacker and Michigan with three tiers of terrace facing the river and the Trump Tower clock face.
Tip: Open every day until midnight, food last call 22:00. The top tier is the photo spot; weekend brunch from 11:00 is the easy walk-in window.
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.
LH Rooftop in Chicago crowns LondonHouse on the corner of Wacker and Michigan with three tiers of terrace facing the river and the Trump Tower clock face.
Tip: Open every day until midnight, food last call 22:00. The top tier is the photo spot; weekend brunch from 11:00 is the easy walk-in window.
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.
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.