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