| Event | Venue | Date/Time | |
| TC Carson | City Winery - Chicago
Chicago, IL | Monday
3/17/2025
7:30 PM |  |
| Ara Dinkjian & Fahir Atakoglu | City Winery - Chicago
Chicago, IL | Tuesday
3/18/2025
7:30 PM | |
| Jack the Whipper | City Winery - Chicago
Chicago, IL | Thursday
3/20/2025
7:30 PM | |
| Anthony David | City Winery - Chicago
Chicago, IL | Friday
3/21/2025
7:30 PM | |
| Rahsaan Patterson | City Winery - Chicago
Chicago, IL | Saturday
3/22/2025
6:00 PM | |
| Rahsaan Patterson | City Winery - Chicago
Chicago, IL | Saturday
3/22/2025
9:30 PM | |
| Joyce Hurley | City Winery - Chicago
Chicago, IL | Sunday
3/23/2025
7:00 PM | |
| Trouble Ahead - Grateful Dead Tribute Nite | City Winery - Chicago
Chicago, IL | Monday
3/24/2025
6:30 PM | |
| Major. | City Winery - Chicago
Chicago, IL | Tuesday
3/25/2025
7:30 PM | |
| ZZ Ward | City Winery - Chicago
Chicago, IL | Wednesday
3/26/2025
7:00 PM | |
| Big Suit - Talking Heads Tribute | City Winery - Chicago
Chicago, IL | Thursday
3/27/2025
7:30 PM | |
| Chuck Ragan | City Winery - Chicago
Chicago, IL | Friday
3/28/2025
7:30 PM | |
| Soul Brunch | City Winery - Chicago
Chicago, IL | Saturday
3/29/2025
12:00 PM | |
| The Verve Pipe | City Winery - Chicago
Chicago, IL | Saturday
3/29/2025
7:30 PM | |
| Classic Album Brunch: Peter Gabriel - SO Live | City Winery - Chicago
Chicago, IL | Sunday
3/30/2025
12:00 PM | |
| Paris Chansons | City Winery - Chicago
Chicago, IL | Sunday
3/30/2025
7:00 PM | |
| K-Love Live | City Winery - Chicago
Chicago, IL | Monday
3/31/2025
7:30 PM | |
| Cyrille Aimee | City Winery - Chicago
Chicago, IL | Tuesday
4/1/2025
7:00 PM | |
| Emery | City Winery - Chicago
Chicago, IL | Wednesday
4/2/2025
7:30 PM | |
| Glen Phillips | City Winery - Chicago
Chicago, IL | Thursday
4/3/2025
7:30 PM | |
| Alejandro Escovedo | City Winery - Chicago
Chicago, IL | Friday
4/4/2025
7:30 PM | |
| Alejandro Escovedo | City Winery - Chicago
Chicago, IL | Saturday
4/5/2025
7:30 PM | |
| The Yacht Rock-ettes | City Winery - Chicago
Chicago, IL | Sunday
4/6/2025
12:00 PM | |
| Lachy Doley | City Winery - Chicago
Chicago, IL | Sunday
4/6/2025
7:00 PM | |
| Mechele - Mary J. Blige Tribute | City Winery - Chicago
Chicago, IL | Monday
4/7/2025
7:30 PM | |
| Keri Johnsrud-Shawn Maxwell Band | City Winery - Chicago
Chicago, IL | Tuesday
4/8/2025
7:30 PM | |
| Heather Shaw | City Winery - Chicago
Chicago, IL | Wednesday
4/9/2025
7:30 PM | |
| AJ Ghent | City Winery - Chicago
Chicago, IL | Thursday
4/10/2025
7:30 PM | |
| Pure Prairie League | City Winery - Chicago
Chicago, IL | Friday
4/11/2025
7:30 PM | |
| Nicholas Tremulis and The Prodigal 9 | City Winery - Chicago
Chicago, IL | Saturday
4/12/2025
7:30 PM | |
| The Ides Of March | City Winery - Chicago
Chicago, IL | Sunday
4/13/2025
2:00 PM | |
| The Ides Of March | City Winery - Chicago
Chicago, IL | Sunday
4/13/2025
7:00 PM | |
| Billy Prine | City Winery - Chicago
Chicago, IL | Monday
4/14/2025
7:30 PM | |
| Samantha Bee | City Winery - Chicago
Chicago, IL | Tuesday
4/15/2025
7:30 PM | |
| Ben Sollee | City Winery - Chicago
Chicago, IL | Thursday
4/17/2025
TBD | |
| American Airlines Global Wine Dinner Series: The James Bond Bordeaux Dinner | City Winery - Chicago
Chicago, IL | Thursday
4/17/2025
6:30 PM | |
| Obisoulstar | City Winery - Chicago
Chicago, IL | Saturday
4/19/2025
7:30 PM | |
| Simply Tina - Tina Turner Tribute | City Winery - Chicago
Chicago, IL | Sunday
4/20/2025
7:00 PM | |
| Luke Combs UK - A Tribute To Luke Combs | City Winery - Chicago
Chicago, IL | Monday
4/21/2025
7:30 PM | |
| A Woman's Words | City Winery - Chicago
Chicago, IL | Wednesday
4/23/2025
7:30 PM | |
| Lady Blackbird | City Winery - Chicago
Chicago, IL | Thursday
4/24/2025
7:30 PM | |
| Classic Albums Live Tribute Show: Tears for Fears - Songs From the Big Chair | City Winery - Chicago
Chicago, IL | Friday
4/25/2025
7:30 PM | |
| Uncorked! - A Cabaret in Cabernet | City Winery - Chicago
Chicago, IL | Saturday
4/26/2025
12:00 PM | |
| Howie Day | City Winery - Chicago
Chicago, IL | Saturday
4/26/2025
7:30 PM | |
| Howie Day | City Winery - Chicago
Chicago, IL | Sunday
4/27/2025
7:30 PM | |
| Blaq Ice | City Winery - Chicago
Chicago, IL | Tuesday
4/29/2025
7:30 PM | |
| Mamrie Hart | City Winery - Chicago
Chicago, IL | Wednesday
4/30/2025
7:30 PM | |
| EXTC | City Winery - Chicago
Chicago, IL | Thursday
5/1/2025
7:30 PM | |
| Martha Wash | City Winery - Chicago
Chicago, IL | Friday
5/2/2025
7:30 PM | |
| Lissie | City Winery - Chicago
Chicago, IL | Saturday
5/3/2025
7:30 PM | |
| Tyler Hilton | City Winery - Chicago
Chicago, IL | Sunday
5/4/2025
7:00 PM | |
| Bad Momz of Comedy | City Winery - Chicago
Chicago, IL | Wednesday
5/7/2025
7:30 PM | |
| Jackopierce | City Winery - Chicago
Chicago, IL | Thursday
5/8/2025
7:30 PM | |
| J. Howell | City Winery - Chicago
Chicago, IL | Saturday
5/10/2025
6:00 PM | |
| J. Howell | City Winery - Chicago
Chicago, IL | Saturday
5/10/2025
9:30 PM | |
| Lynne Jordan | City Winery - Chicago
Chicago, IL | Sunday
5/11/2025
7:00 PM | |
| Lalah Hathaway | City Winery - Chicago
Chicago, IL | Monday
5/12/2025
6:00 PM | |
| Lalah Hathaway | City Winery - Chicago
Chicago, IL | Monday
5/12/2025
9:30 PM | |
| Lalah Hathaway | City Winery - Chicago
Chicago, IL | Tuesday
5/13/2025
6:00 PM | |
| Lalah Hathaway | City Winery - Chicago
Chicago, IL | Tuesday
5/13/2025
9:30 PM | |
| Lalah Hathaway | City Winery - Chicago
Chicago, IL | Wednesday
5/14/2025
6:00 PM | |
| Lalah Hathaway | City Winery - Chicago
Chicago, IL | Wednesday
5/14/2025
9:30 PM | |
| Dan Rodriguez | City Winery - Chicago
Chicago, IL | Thursday
5/15/2025
7:30 PM | |
| Asher Roth | City Winery - Chicago
Chicago, IL | Friday
5/16/2025
7:30 PM | |
| Ramirez and His Flawless Immaculates | City Winery - Chicago
Chicago, IL | Saturday
5/17/2025
7:30 PM | |
| Fly Guy Byrd | City Winery - Chicago
Chicago, IL | Monday
5/19/2025
7:30 PM | |
| Simrit Kaur | City Winery - Chicago
Chicago, IL | Wednesday
5/21/2025
7:30 PM | |
| Dave Hollister | City Winery - Chicago
Chicago, IL | Thursday
5/22/2025
6:00 PM | |
| Dave Hollister | City Winery - Chicago
Chicago, IL | Thursday
5/22/2025
9:30 PM | |
| Dave Hollister | City Winery - Chicago
Chicago, IL | Friday
5/23/2025
6:00 PM | |
| Dave Hollister | City Winery - Chicago
Chicago, IL | Friday
5/23/2025
9:30 PM | |
| Songs in the Key of Stevie - Stevie Wonder Tribute | City Winery - Chicago
Chicago, IL | Sunday
5/25/2025
7:00 PM | |
| The Garcia Project - Tribute to Jerry Garcia | City Winery - Chicago
Chicago, IL | Monday
5/26/2025
7:30 PM | |
| Nikka Costa | City Winery - Chicago
Chicago, IL | Tuesday
5/27/2025
7:30 PM | |
| The Klezmatics | City Winery - Chicago
Chicago, IL | Wednesday
5/28/2025
7:30 PM | |
| Bob Schneider | City Winery - Chicago
Chicago, IL | Saturday
5/31/2025
7:30 PM | |
| Garrison Keillor | City Winery - Chicago
Chicago, IL | Thursday
6/12/2025
7:30 PM | |
| The Samples | City Winery - Chicago
Chicago, IL | Friday
6/13/2025
7:30 PM | |
| Scott Thompson | City Winery - Chicago
Chicago, IL | Sunday
6/15/2025
7:00 PM | |
| American Airlines Global Wine Dinner Series: The Great Wines of Piedmont | City Winery - Chicago
Chicago, IL | Thursday
6/19/2025
6:30 PM | |
| Corky Siegel | City Winery - Chicago
Chicago, IL | Sunday
6/22/2025
7:00 PM | |
| After 7 | City Winery - Chicago
Chicago, IL | Friday
6/27/2025
6:00 PM | |
| After 7 | City Winery - Chicago
Chicago, IL | Friday
6/27/2025
9:30 PM | |
| After 7 | City Winery - Chicago
Chicago, IL | Saturday
6/28/2025
6:00 PM | |
| After 7 | City Winery - Chicago
Chicago, IL | Saturday
6/28/2025
9:30 PM | |
| Babatunde HipHopera | City Winery - Chicago
Chicago, IL | Monday
6/30/2025
7:30 PM | |
| Jason Ladanye | City Winery - Chicago
Chicago, IL | Friday
7/11/2025
7:30 PM | |
| Chuck Prophet and His Cumbia Shoes | City Winery - Chicago
Chicago, IL | Saturday
7/12/2025
7:30 PM | |
| Griffin House | City Winery - Chicago
Chicago, IL | Sunday
7/13/2025
7:00 PM | |
| Goalden Chyld | City Winery - Chicago
Chicago, IL | Wednesday
7/16/2025
7:30 PM | |
| Unteachables Comedy Tour | City Winery - Chicago
Chicago, IL | Sunday
7/20/2025
7:00 PM | |
| Nurses Night Out | City Winery - Chicago
Chicago, IL | Wednesday
7/23/2025
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Thursday
7/24/2025
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Friday
7/25/2025
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Saturday
7/26/2025
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Sunday
7/27/2025
7:00 PM | |
| Christian Johnson | City Winery - Chicago
Chicago, IL | Thursday
7/31/2025
7:30 PM | |
| John Violinist | City Winery - Chicago
Chicago, IL | Friday
8/8/2025
7:30 PM | |
| Jagged Little Pill | City Winery - Chicago
Chicago, IL | Thursday
8/28/2025
7:30 PM | |
