| Event | Venue |  Date/Time | |
| Joshua Radin | City Winery - Chicago
Chicago, IL | Sunday
11/8/2026
7:00 PM |  |
| Joshua Radin | City Winery - Chicago
Chicago, IL | Saturday
11/7/2026
7:30 PM | |
| Davide De Pierro | City Winery - Chicago
Chicago, IL | Thursday
10/22/2026
7:30 PM | |
| Bob Schneider | City Winery - Chicago
Chicago, IL | Friday
10/16/2026
7:30 PM | |
| Martin Sexton | City Winery - Chicago
Chicago, IL | Friday
10/9/2026
9:30 PM | |
| Martin Sexton | City Winery - Chicago
Chicago, IL | Friday
10/9/2026
6:00 PM | |
| Lyfe Jennings | City Winery - Chicago
Chicago, IL | Friday
9/4/2026
9:30 PM | |
| Lyfe Jennings | City Winery - Chicago
Chicago, IL | Friday
9/4/2026
6:00 PM | |
| Lyfe Jennings | City Winery - Chicago
Chicago, IL | Thursday
9/3/2026
7:30 PM | |
| O-Town | City Winery - Chicago
Chicago, IL | Sunday
8/30/2026
7:00 PM | |
| Goapele | City Winery - Chicago
Chicago, IL | Saturday
8/29/2026
8:30 PM | |
| Goapele | City Winery - Chicago
Chicago, IL | Saturday
8/29/2026
5:00 PM | |
| Esperanza Spalding | City Winery - Chicago
Chicago, IL | Sunday
8/23/2026
7:00 PM | |
| Esperanza Spalding | City Winery - Chicago
Chicago, IL | Saturday
8/22/2026
7:30 PM | |
| Esperanza Spalding | City Winery - Chicago
Chicago, IL | Friday
8/21/2026
7:30 PM | |
| Android Paranoid - Tribute to Radiohead | City Winery - Chicago
Chicago, IL | Thursday
8/20/2026
7:30 PM | |
| Christian Johnson | City Winery - Chicago
Chicago, IL | Sunday
8/16/2026
7:00 PM | |
| Gary Thomas: Sinatra Brunch | City Winery - Chicago
Chicago, IL | Sunday
8/16/2026
12:00 PM | |
| Kenyon Dixon | City Winery - Chicago
Chicago, IL | Saturday
8/15/2026
7:00 PM | |
| J. Holiday | City Winery - Chicago
Chicago, IL | Friday
8/14/2026
7:30 PM | |
| Trey Daniels | City Winery - Chicago
Chicago, IL | Thursday
8/13/2026
7:30 PM | |
| Bebel Gilberto | City Winery - Chicago
Chicago, IL | Wednesday
8/12/2026
7:30 PM | |
| Mohini Dey | City Winery - Chicago
Chicago, IL | Tuesday
8/11/2026
9:30 PM | |
| Mohini Dey | City Winery - Chicago
Chicago, IL | Tuesday
8/11/2026
6:00 PM | |
| Lisa Knowles Smith | City Winery - Chicago
Chicago, IL | Sunday
8/9/2026
7:00 PM | |
| D'Lai | City Winery - Chicago
Chicago, IL | Saturday
8/8/2026
7:30 PM | |
| Glenn Jones | City Winery - Chicago
Chicago, IL | Saturday
8/8/2026
5:00 PM | |
| R&B Brunch | City Winery - Chicago
Chicago, IL | Saturday
8/8/2026
12:00 PM | |
| Melanie Fiona | City Winery - Chicago
Chicago, IL | Friday
8/7/2026
9:30 PM | |
| Melanie Fiona | City Winery - Chicago
Chicago, IL | Friday
8/7/2026
6:00 PM | |
| T.K. Kirkland | City Winery - Chicago
Chicago, IL | Thursday
8/6/2026
7:30 PM | |
| Babatunde HipHopera | City Winery - Chicago
Chicago, IL | Monday
8/3/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Sunday
8/2/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Saturday
8/1/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Friday
7/31/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Thursday
7/30/2026
7:30 PM | |
| Vernard | City Winery - Chicago
Chicago, IL | Tuesday
7/28/2026
7:30 PM | |
| Simply The Best - Tina Turner Tribute | City Winery - Chicago
Chicago, IL | Monday
7/27/2026
7:30 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Sunday
7/26/2026
4:00 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Saturday
7/25/2026
7:30 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Saturday
7/25/2026
4:00 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Friday
7/24/2026
7:30 PM | |
| AJ Ghent | City Winery - Chicago
Chicago, IL | Thursday
7/23/2026
7:30 PM | |
| Suzie Toot | City Winery - Chicago
Chicago, IL | Wednesday
7/22/2026
7:30 PM | |
| Keiko Matsui | City Winery - Chicago
Chicago, IL | Tuesday
7/21/2026
7:30 PM | |
| David Cook | City Winery - Chicago
Chicago, IL | Sunday
7/19/2026
7:00 PM | |
| Elizabeth Brunot | City Winery - Chicago
Chicago, IL | Saturday
7/18/2026
8:00 PM | |
| John Violinist | City Winery - Chicago
Chicago, IL | Friday
7/17/2026
9:30 PM | |
| John Violinist | City Winery - Chicago
Chicago, IL | Friday
7/17/2026
6:00 PM | |
| Jill Andrews | City Winery - Chicago
Chicago, IL | Thursday
7/16/2026
7:30 PM | |
| Hip Hop Unplugged | City Winery - Chicago
Chicago, IL | Wednesday
7/15/2026
7:30 PM | |
| Just Fine - Mary J. Blige Tribute Band | City Winery - Chicago
Chicago, IL | Tuesday
7/14/2026
7:30 PM | |
| Souls of Mischief | City Winery - Chicago
Chicago, IL | Monday
7/13/2026
7:30 PM | |
| Miki Howard | City Winery - Chicago
Chicago, IL | Sunday
7/12/2026
7:00 PM | |
| Hip Hop and R&B Bingo With Tom Swoope | City Winery - Chicago
Chicago, IL | Saturday
7/11/2026
9:30 PM | |
| The Session R&B Jam | City Winery - Chicago
Chicago, IL | Friday
7/10/2026
7:30 PM | |
| The Samples | City Winery - Chicago
Chicago, IL | Thursday
7/9/2026
7:30 PM | |
| BBMak | City Winery - Chicago
Chicago, IL | Wednesday
7/8/2026
7:30 PM | |
| Dustin Ross - Comedy | City Winery - Chicago
Chicago, IL | Tuesday
7/7/2026
7:30 PM | |
| Robopocalypse - The Musical! | City Winery - Chicago
Chicago, IL | Sunday
7/5/2026
7:00 PM | |
| Glenn Jones | City Winery - Chicago
Chicago, IL | Saturday
7/4/2026
8:30 PM | |
| Glenn Jones | City Winery - Chicago
Chicago, IL | Saturday
7/4/2026
5:00 PM | |
| TC Carson | City Winery - Chicago
Chicago, IL | Friday
7/3/2026
7:30 PM | |
| Mindi Abair | City Winery - Chicago
Chicago, IL | Thursday
7/2/2026
7:30 PM | |
| Maui The Writer | City Winery - Chicago
Chicago, IL | Wednesday
7/1/2026
7:30 PM | |
| BETH | City Winery - Chicago
Chicago, IL | Monday
6/29/2026
7:30 PM | |
| Whine Down with Jana Kramer And Friends | City Winery - Chicago
Chicago, IL | Sunday
6/28/2026
7:00 PM | |
| Whine Down with Jana Kramer And Friends | City Winery - Chicago
Chicago, IL | Saturday
6/27/2026
7:30 PM | |
| Jamal Roberts | City Winery - Chicago
Chicago, IL | Friday
6/26/2026
7:30 PM | |
| Mob Wives | City Winery - Chicago
Chicago, IL | Thursday
6/25/2026
7:30 PM | |
| AJ McQueen | City Winery - Chicago
Chicago, IL | Wednesday
6/24/2026
7:30 PM | |
| J Dilla Tribute | City Winery - Chicago
Chicago, IL | Tuesday
6/23/2026
7:30 PM | |
| Nikita Nichelle | City Winery - Chicago
Chicago, IL | Monday
6/22/2026
7:30 PM | |
| Kathy Mattea | City Winery - Chicago
Chicago, IL | Sunday
6/21/2026
7:00 PM | |
| Rahsaan Patterson | City Winery - Chicago
Chicago, IL | Saturday
6/20/2026
9:30 PM | |
| Rahsaan Patterson | City Winery - Chicago
Chicago, IL | Saturday
6/20/2026
6:00 PM | |
| Alan Hewitt | City Winery - Chicago
Chicago, IL | Saturday
6/20/2026
12:00 PM | |
| Rita Wilson | City Winery - Chicago
Chicago, IL | Friday
6/19/2026
7:30 PM | |
| Midnight Sun | City Winery - Chicago
Chicago, IL | Wednesday
6/17/2026
7:30 PM | |
| Amy Grant | City Winery - Chicago
Chicago, IL | Monday
6/15/2026
7:30 PM | |
| Marc E. Bassy | City Winery - Chicago
Chicago, IL | Sunday
6/14/2026
7:30 PM | |
| Nathan Chester and The Old Soul's Motown Revival Brunch | City Winery - Chicago
Chicago, IL | Sunday
6/14/2026
12:00 PM | |
| Kevin Ross | City Winery - Chicago
Chicago, IL | Saturday
6/13/2026
8:30 PM | |
| Kevin Ross | City Winery - Chicago
Chicago, IL | Saturday
6/13/2026
5:00 PM | |
| Tyler Hilton & Kate Voegele | City Winery - Chicago
Chicago, IL | Friday
6/12/2026
7:30 PM | |
| Michael Lington & Paul Taylor | City Winery - Chicago
Chicago, IL | Thursday
6/11/2026
7:30 PM | |
| Lyle Lovett | City Winery - Chicago
Chicago, IL | Wednesday
6/10/2026
7:30 PM | |
| Lyle Lovett | City Winery - Chicago
Chicago, IL | Tuesday
6/9/2026
7:30 PM | |
| Lyle Lovett | City Winery - Chicago
Chicago, IL | Monday
6/8/2026
7:30 PM | |
| Lyle Lovett | City Winery - Chicago
Chicago, IL | Sunday
6/7/2026
7:30 PM | |
| Sejoe | City Winery - Chicago
Chicago, IL | Friday
6/5/2026
7:00 PM | |
| Funkadesi | City Winery - Chicago
Chicago, IL | Thursday
6/4/2026
7:30 PM | |
| Big Bad Wolf Comedy | City Winery - Chicago
Chicago, IL | Wednesday
6/3/2026
7:30 PM | |
| Alvin Garrett | City Winery - Chicago
Chicago, IL | Tuesday
6/2/2026
7:30 PM | |
| Is This Going to Cause an Argument | City Winery - Chicago
Chicago, IL | Monday
6/1/2026
7:30 PM | |
| Highway Dream - 50 Years of Tom Petty Tribute Brunch | City Winery - Chicago
Chicago, IL | Sunday
5/31/2026
12:00 PM | |
| Steam Powered Giraffe | City Winery - Chicago
Chicago, IL | Saturday
5/30/2026
7:30 PM | |
| The Jussoul Experience Brunch | City Winery - Chicago
Chicago, IL | Saturday
5/30/2026
12:00 PM | |
| Jeff Mauro | City Winery - Chicago
Chicago, IL | Friday
5/29/2026
7:30 PM | |
| Nunnabove | City Winery - Chicago
Chicago, IL | Thursday
5/28/2026
7:30 PM | |
