Empty Bottle ★ 4.7
$Wicker Park / Bucktown{'monday': '17:00-02:00', 'tuesday': '17:00-02:00', 'wednesday': '17:00-02:00', 'thursday': '17:00-02:00', 'friday': '17:00-02:00', 'saturday': '17:00-03:00', 'sunday': '17:00-02:00'}
Empty Bottle on North Western has hosted indie, punk and experimental music in Ukrainian Village since 1992 and turned 33 in 2025, with free Monday night residencies that still anchor the calendar.
Tip: Open daily 17:00-02:00, Saturday until 03:00. Monday's free residency is the easy walk-in entry to the scene. Pizza Friendly Pizza is next door.
Schubas Tavern ★ 4.6
$$Wrigleyville / Lakeview{'monday': '18:00-23:00', 'tuesday': '17:00-23:00', 'wednesday': '17:00-23:00', 'thursday': '17:00-00:00', 'friday': '17:00-01:00', 'saturday': '14:00-01:00', 'sunday': '18:00-23:00'}
Schubas Tavern in Chicago has run live music seven nights a week in the 1903 Schlitz tied-house on Southport since 1989, from honky-tonk to indie rock to Americana.
Tip: Doors usually 19:00, show at 20:00. The back room holds 165 standing; the front bar runs into the late hours after the night's show ends.
The Hideout ★ 4.7
$$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.
Thalia Hall ★ 4.7
$$Pilsen{'monday': 'varies by event', 'tuesday': 'varies by event', 'wednesday': 'varies by event', 'thursday': '19:00 doors, varies', 'friday': '19:00 doors, varies', 'saturday': '19:00 doors, varies', 'sunday': 'varies by event'}
Thalia Hall in Pilsen, built 1892 and modeled on the Prague State Opera House, runs touring indie, hip-hop and electronic shows in an 800-capacity balcony room.
Tip: Doors usually 19:00 with show at 20:00. The balcony bench seating fills first; Dusek's restaurant and Punch House bar share the building entrance.
Buddy Guy's Legends ★ 4.7
$$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.