Price$$
NeighbourhoodWrigleyville / Lakeview
Hours{'monday': '18:00-23:00', 'tuesday': '17:00-23:00', 'wednesday': '17:00-23:00', 'thursday': '17:00-00:00', 'friday': '17:00-01:00', 'saturday': '14:00-01:00', 'sunday': '18:00-23:00'}

Tip: Doors usually 19:00, show at 20:00. The back room holds 165 standing; the front bar runs into the late hours after the night's show ends.

Location

Address: 3159 N Southport Ave, Chicago, IL 60657

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The Hideout ★ 4.7

$$Wicker Park / Bucktown{'monday': 'varies by event', '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': 'varies by event'}

The Hideout in Chicago is the Wabansia Avenue clapboard cottage in the Elston industrial corridor, hosting Americana, experimental and the Robbie Fulks Monday residency.

Tip: Tuesday through Thursday close at midnight, Friday and Saturday at 01:00. The room holds about 100 and the bands play through the bar conversation.

1354 W Wabansia Ave, Chicago, IL 60642

Thalia Hall ★ 4.7

$$Pilsen{'monday': 'varies by event', 'tuesday': 'varies by event', 'wednesday': 'varies by event', 'thursday': '19:00 doors, varies', 'friday': '19:00 doors, varies', 'saturday': '19:00 doors, varies', 'sunday': 'varies by event'}

Thalia Hall in Pilsen, built 1892 and modeled on the Prague State Opera House, runs touring indie, hip-hop and electronic shows in an 800-capacity balcony room.

Tip: Doors usually 19:00 with show at 20:00. The balcony bench seating fills first; Dusek's restaurant and Punch House bar share the building entrance.

1807 S Allport St, Chicago, IL 60608

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.

700 S Wabash Ave, Chicago, IL 60605

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.

12 S Michigan Ave, Chicago, IL 60603

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.

85 E Wacker Dr, Chicago, IL 60601

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.

2018 W North Ave, Chicago, IL 60647

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