Chicago Live Music From Arena Roar to Piano Sing-Alongs
Sip Asian-inspired cocktails with small bites behind an understated entrance, or settle into a former carriage house. Check arena performance times before arranging the evening, and allow for a possible wait at the cocktail bar.
South Loop, Chinatown, Pilsen
South Loop Show Scale
Wintrust Arena hosts major concerts and comedy shows at 200 E Cermak Road. The WNBA's Chicago Sky also plays here. Strong sightlines and high-energy acoustics define the room. Review the strict bag policy before packing for a weekend show. Restroom and concession queues can run long. Drinks carry high prices. Check the current event schedule for exact performance times before planning the rest of the night around an arena visit.
Chinatown Nightcap
Behind Moon Palace Express, Nine Bar stays open until 2:00 AM on Friday and Saturday. A small sign marks the entrance at 216 W Cermak Road. Entry is free. A short wait at the door is possible. Cocktails use Asian spirits and ingredients alongside American classics. Pair a drink with crab rangoons from the concise snack menu. Illuminated bottle shelves flank a decorative fan on the back wall.
Pilsen at the Keys
Weekend piano-bar sing-alongs are part of the lineup at Tack Room, a former carriage house within the Thalia Hall complex. Casual live guitar also features here. The upstairs room sits behind a staircase at 1807 S Allport St. Admission is limited to guests 21 and over. Entry is free. Friday and Saturday hours run from 7:00 PM to 1:00 AM. Try the small bites sourced from next door with a cocktail.
