Buddy Guy's Legends ★ 4.7
$$$$
The LoopWed-Thu 17:00-00:00, Fri-Sat 17:00-01:30, Sun 17:00-00:00. Closed Mon-Tue.
Buddy Guy's Legends in Chicago is the South Wabash blues room the man himself opened in 1989 and where he still plays a residency every January.
TipClosed Monday and Tuesday. Wednesday and Thursday close at midnight; weekends run to 01:30. Cover usually $20, kitchen serves Louisiana barbecue.
Cindy's at Chicago Athletic Association ★ 4.5
$$$$
$22 cocktails, reservations via OpenTableThe LoopMon-Thu 11:00-23:00, Fri 11:00-00:00, Sat 10:00-00:00, Sun 10:00-23:00.
Cindy's rooftop in Chicago sits on the 13th floor of the Chicago Athletic Association with all-season terrace seating that frames Millennium Park and Lake Michigan.
TipWeekends fill from 21:00; reserve via OpenTable or arrive at 16:00 for the sunset window. The terrace stays heated and open year-round.
LH Rooftop ★ 4.4
$$$$
$20 cocktails, OpenTable reservationsThe LoopDaily 11:00-00:00.
LH Rooftop in Chicago crowns LondonHouse on the corner of Wacker and Michigan with three tiers of terrace facing the river and the Trump Tower clock face.
TipOpen every day until midnight, food last call 22:00. The top tier is the photo spot; weekend brunch from 11:00 is the easy walk-in window.
The Up Room ★ 4.3
$$$$
$18 cocktails, walk-in or OpenTableWicker Park / BucktownMon-Thu 17:00-00:00, Fri-Sat 17:00-01:00, Sun 17:00-00:00.
The Up Room crowns the 13th floor of The Robey, Wicker Park's tallest building, with a wraparound terrace facing the Loop skyline and the six-corners street.
TipOpen daily from 17:00, weekends until 01:00. Sunset window books fast; weeknights walk in easy and the inside lounge stays open in winter.
The Aviary ★ 4.7
$$$$
West LoopTue-Thu 17:00-00:00, Fri 17:00-01:00, Sat 16:30-01:00. Closed Mon/Sun.
The Aviary in Chicago opened 2011 as Grant Achatz's Alinea Group cocktail lab, applying fine-dining technique to a five-course tasting of cocktails paired with small plates.
TipTock reservations only, no walk-ins. The seasonal 5-course tasting is $145; sit at the bar to watch the kitchen build the drinks.
The Office ★ 4.8
$$$$
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.