| Nurses Night Out | 4-20-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| PureSoul - A Tribute to The Smiths | 4-21-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Howie Day | 4-22-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Sons of the Silent Age: The Cracked Actor Cabaret - David Bowie Songbook | 4-23-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| The Big Wu | 4-24-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Fred Hammond | 4-25-2026
Saturday
5:00 PM | City Winery in Chicago, IL | View Tickets |
| Fred Hammond | 4-25-2026
Saturday
8:30 PM | City Winery in Chicago, IL | View Tickets |
| Soul Brunch | 4-26-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| CusCampbell | 4-26-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Colin James, Matt Andersen & Terra Lightfoot | 4-27-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Vanessa Carlton | 4-28-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Vanessa Carlton | 4-29-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| The Special Consensus | 4-30-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Jeff Mauro | 5-1-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Brunch with Ian Maksin & Gabriel Datcu | 5-2-2026
Saturday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Rakim | 5-2-2026
Saturday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Rakim | 5-2-2026
Saturday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Gospel Melodies Day Party & Brunch | 5-3-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| House Guest Live ft. Scott Evans | 5-3-2026
Sunday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| The Word Up Story | 5-4-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Ruben Ramirez | 5-5-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| George Willborn | 5-6-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Eric Bellinger | 5-7-2026
Thursday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Eric Bellinger | 5-7-2026
Thursday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Tasha K | 5-8-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Anna Konkle | 5-9-2026
Saturday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Twista | 5-9-2026
Saturday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Twista | 5-9-2026
Saturday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Mother's Day Brunch | 5-10-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Tacarra Williams | 5-10-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| David Broza | 5-11-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Motown Mothers versus Modern Daughters | 5-12-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Chantal Kreviazuk | 5-13-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Karla Bonoff | 5-14-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Davide De Pierro | 5-15-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Davide De Pierro | 5-16-2026
Saturday
3:00 PM | City Winery in Chicago, IL | View Tickets |
| Davide De Pierro | 5-16-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Ann Wilson | 5-17-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Ann Wilson | 5-17-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| The Mama's Den Podcast Live! | 5-18-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Brad Kofman & Friends | 5-19-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Puresoul - Tribute to Stevie Wonder | 5-20-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| The Klezmatics | 5-21-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| The Voices - Tribute to Motown | 5-22-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Fallout Funny Comedy Tour | 5-23-2026
Saturday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Fallout Funny Comedy Tour | 5-23-2026
Saturday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Hamilton Sing-Along Drag Brunch | 5-24-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Murphy Lee and Kyjuan | 5-24-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Shea Butta Band | 5-25-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Major. | 5-26-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Obisoulstar | 5-27-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Nunnabove | 5-28-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Jeff Mauro | 5-29-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| The Jussoul Experience Brunch | 5-30-2026
Saturday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Steam Powered Giraffe | 5-30-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Highway Dream - 50 Years of Tom Petty Tribute Brunch | 5-31-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Lisa Marie Lovett | 5-31-2026
Sunday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Is This Going to Cause an Argument | 6-1-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Alvin Garrett | 6-2-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Funkadesi | 6-4-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Sejoe | 6-5-2026
Friday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Rita Wilson | 6-6-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Lyle Lovett | 6-7-2026
Sunday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Lyle Lovett | 6-8-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Lyle Lovett | 6-9-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Lyle Lovett | 6-10-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Michael Lington & Paul Taylor | 6-11-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Tyler Hilton & Kate Voegele | 6-12-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Kevin Ross | 6-13-2026
Saturday
5:00 PM | City Winery in Chicago, IL | View Tickets |
| Kevin Ross | 6-13-2026
Saturday
8:30 PM | City Winery in Chicago, IL | View Tickets |
| Nathan Chester and The Old Soul's Motown Revival Brunch | 6-14-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Marc E. Bassy | 6-14-2026
Sunday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Amy Grant | 6-15-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Midnight Sun | 6-17-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Alan Hewitt | 6-20-2026
Saturday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Kathy Mattea | 6-21-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Nikita Nichelle | 6-22-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Mob Wives | 6-25-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Jamal Roberts | 6-26-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Whine Down with Jana Kramer And Friends | 6-27-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Whine Down with Jana Kramer And Friends | 6-28-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Mindi Abair | 7-2-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| TC Carson | 7-3-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Glenn Jones | 7-4-2026
Saturday
5:00 PM | City Winery in Chicago, IL | View Tickets |
| Glenn Jones | 7-4-2026
Saturday
8:30 PM | City Winery in Chicago, IL | View Tickets |
| BBMak | 7-8-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| The Samples | 7-9-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Hip Hop and R&B Bingo With Tom Swoope | 7-11-2026
Saturday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Hip Hop and R&B Bingo With Tom Swoope | 7-11-2026
Saturday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Miki Howard | 7-12-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Souls of Mischief | 7-13-2026
Monday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Just Fine - Mary J. Blige Tribute Band | 7-14-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Hip Hop Unplugged | 7-15-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Jill Andrews | 7-16-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| John Violinist | 7-17-2026
Friday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| John Violinist | 7-17-2026
Friday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Elizabeth Brunot | 7-18-2026
Saturday
8:00 PM | City Winery in Chicago, IL | View Tickets |
| David Cook | 7-19-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Keiko Matsui | 7-21-2026
Tuesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Suzie Toot | 7-22-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| AJ Ghent | 7-23-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Nephew Tommy | 7-24-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Nephew Tommy | 7-25-2026
Saturday
4:00 PM | City Winery in Chicago, IL | View Tickets |
| Nephew Tommy | 7-25-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Nephew Tommy | 7-26-2026
Sunday
4:00 PM | City Winery in Chicago, IL | View Tickets |
| Eric Roberson | 7-29-2026
Wednesday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Eric Roberson | 7-30-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Eric Roberson | 7-31-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Eric Roberson | 8-1-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Eric Roberson | 8-2-2026
Sunday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| R&B Brunch | 8-8-2026
Saturday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Glenn Jones | 8-8-2026
Saturday
5:00 PM | City Winery in Chicago, IL | View Tickets |
| D'Lai | 8-8-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Lisa Knowles Smith | 8-9-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Mohini Dey | 8-11-2026
Tuesday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Mohini Dey | 8-11-2026
Tuesday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Trey Daniels | 8-13-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| J. Holiday | 8-14-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Gary Thomas: Sinatra Brunch | 8-16-2026
Sunday
12:00 PM | City Winery in Chicago, IL | View Tickets |
| Christian Johnson | 8-16-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Android Paranoid - Tribute to Radiohead | 8-20-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Esperanza Spalding | 8-21-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Esperanza Spalding | 8-22-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Esperanza Spalding | 8-23-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Goapele | 8-29-2026
Saturday
5:00 PM | City Winery in Chicago, IL | View Tickets |
| Goapele | 8-29-2026
Saturday
8:30 PM | City Winery in Chicago, IL | View Tickets |
| O-Town | 8-30-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
| Lyfe Jennings | 9-3-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Lyfe Jennings | 9-4-2026
Friday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Lyfe Jennings | 9-4-2026
Friday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Martin Sexton | 10-9-2026
Friday
6:00 PM | City Winery in Chicago, IL | View Tickets |
| Martin Sexton | 10-9-2026
Friday
9:30 PM | City Winery in Chicago, IL | View Tickets |
| Bob Schneider | 10-16-2026
Friday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Davide De Pierro | 10-22-2026
Thursday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Joshua Radin | 11-7-2026
Saturday
7:30 PM | City Winery in Chicago, IL | View Tickets |
| Joshua Radin | 11-8-2026
Sunday
7:00 PM | City Winery in Chicago, IL | View Tickets |
