City Winery Chicago is an urban winery, restaurant, and intimate concert venue at 1200 W. Randolph Street in the West Loop. Its roughly 300-seat Main Stage pairs live shows with full table service — chef-driven food and wines made on site — in a dinner-and-a-show format that spans national touring musicians, R&B and soul, jazz, tribute nights, brunch shows, and marquee standup comedy (recent bookings include DL Hughley, Nephew Tommy, T.K. Kirkland, and D'Lai). With reserved seating and an intimate room, shows regularly sell out in advance.
Jazmyn W
7:30 PMThu, Oct 1$25 – $45
It's Raining Queens
7:30 PMSat, Oct 3$55 – $75
Kennedy Ryon - The Can We Evolve? Tour
7:30 PMMon, Oct 5$30 – $45
Cousin Tiera
7:30 PMMon, Nov 30$45 – $65
DL Hughley
6:00 PMFri, Dec 18$45 – $69
DL Hughley
9:30 PMFri, Dec 18$45 – $69
DL Hughley
6:00 PMSat, Dec 19$45 – $69
DL Hughley
9:30 PMSat, Dec 19$45 – $69
DL Hughley
5:00 PMSun, Dec 20$45 – $69
DL Hughley
8:30 PMSun, Dec 20$45 – $69
None of the comedians you follow are on the lineup here right now.
Check the venue's website2026
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Christian Johnson
7:00 PMSun, Aug 16$35 – $55
D'Lai: I Beg Your Pardon Tour
7:30 PMSat, Aug 8$32 – $49
City Of Laughs Presents
7:30 PMThu, Aug 6$35 – $55Sold out
Lady Bunny in Bunny Butchers Broadway
7:30 PMWed, Jul 29$20 – $35
Nephew Tommy
4:00 PMSun, Jul 26$40 – $65
Nephew Tommy
7:30 PMSat, Jul 25$40 – $65Sold out
Nephew Tommy
4:00 PMSat, Jul 25$40 – $65
Nephew Tommy
7:30 PMFri, Jul 24$40 – $65
Every comedian who's been on a lineup at City Winery Chicago.