| Event | Venue |  Date/Time | |
| An Evening of Yacht Rock | City Winery - Chicago
Chicago, IL | Monday
9/1/2025
7:30 PM |  |
| Lloyd Cole | City Winery - Chicago
Chicago, IL | Tuesday
9/2/2025
7:30 PM | |
| Kofi B | City Winery - Chicago
Chicago, IL | Wednesday
9/3/2025
7:30 PM | |
| The Music of David Sanborn - Tribute | City Winery - Chicago
Chicago, IL | Thursday
9/4/2025
7:30 PM | |
| Loni Love | City Winery - Chicago
Chicago, IL | Friday
9/5/2025
7:30 PM | |
| Sounds Of Blackness | City Winery - Chicago
Chicago, IL | Saturday
9/6/2025
7:30 PM | |
| Gettin' Grown Podcast Live | City Winery - Chicago
Chicago, IL | Sunday
9/7/2025
12:00 PM | |
| Gunhild Carling | City Winery - Chicago
Chicago, IL | Sunday
9/7/2025
7:00 PM | |
| Teddy's Jams - A Tribute to Blackstreet and Guy | City Winery - Chicago
Chicago, IL | Monday
9/8/2025
7:30 PM | |
| Torri Griffin & Isa | City Winery - Chicago
Chicago, IL | Tuesday
9/9/2025
7:30 PM | |
| Infinite 80s - Tribute | City Winery - Chicago
Chicago, IL | Wednesday
9/10/2025
7:30 PM | |
| Emo Prom Nite | City Winery - Chicago
Chicago, IL | Friday
9/12/2025
7:30 PM | |
| B5 | City Winery - Chicago
Chicago, IL | Saturday
9/13/2025
7:30 PM | |
| Marshall Crenshaw | City Winery - Chicago
Chicago, IL | Sunday
9/14/2025
7:00 PM | |
| Funkadesi | City Winery - Chicago
Chicago, IL | Monday
9/15/2025
7:30 PM | |
| Sandy Redd & Mario Canon | City Winery - Chicago
Chicago, IL | Tuesday
9/16/2025
7:30 PM | |
| Shahar Cohen | City Winery - Chicago
Chicago, IL | Wednesday
9/17/2025
7:30 PM | |
| R&B Afterdark | City Winery - Chicago
Chicago, IL | Friday
9/19/2025
7:30 PM | |
| Anthony Rapp | City Winery - Chicago
Chicago, IL | Sunday
9/21/2025
7:00 PM | |
| The Seven Wonders - Fleetwood Mac Tribute | City Winery - Chicago
Chicago, IL | Monday
9/22/2025
7:30 PM | |
| Through The Griffin Tour: The Super Carlin Brothers | City Winery - Chicago
Chicago, IL | Tuesday
9/23/2025
7:30 PM | |
| Jazmyn W | City Winery - Chicago
Chicago, IL | Thursday
9/25/2025
7:30 PM | |
| Ami Taf Ra | City Winery - Chicago
Chicago, IL | Friday
9/26/2025
7:30 PM | |
| Hip Hop and R&B Bingo With Tom Swoope | City Winery - Chicago
Chicago, IL | Sunday
9/28/2025
5:00 PM | |
| Hip Hop and R&B Bingo With Tom Swoope | City Winery - Chicago
Chicago, IL | Sunday
9/28/2025
8:30 PM | |
| Vernard | City Winery - Chicago
Chicago, IL | Tuesday
9/30/2025
7:30 PM | |
| Luenell | City Winery - Chicago
Chicago, IL | Wednesday
10/1/2025
6:00 PM | |
| Luenell | City Winery - Chicago
Chicago, IL | Wednesday
10/1/2025
9:30 PM | |
| Luenell | City Winery - Chicago
Chicago, IL | Thursday
10/2/2025
6:00 PM | |
| Luenell | City Winery - Chicago
Chicago, IL | Thursday
10/2/2025
9:30 PM | |
| Neo Soul Love - Tribute to Erykah Badu and Jill Scott | City Winery - Chicago
Chicago, IL | Saturday
10/4/2025
7:30 PM | |
| Surabhi Ensemble & Las Guitarras de Espana | City Winery - Chicago
Chicago, IL | Monday
10/6/2025
7:30 PM | |
| The Impossible Fortune | City Winery - Chicago
Chicago, IL | Tuesday
10/7/2025
7:30 PM | |
| Judith Hill | City Winery - Chicago
Chicago, IL | Thursday
10/9/2025
7:30 PM | |
| George Wallace | City Winery - Chicago
Chicago, IL | Sunday
10/12/2025
5:00 PM | |
| George Wallace | City Winery - Chicago
Chicago, IL | Sunday
10/12/2025
8:30 PM | |
| Bruce McCulloch | City Winery - Chicago
Chicago, IL | Friday
10/24/2025
7:30 PM | |
| Young Gun Silver Fox | City Winery - Chicago
Chicago, IL | Saturday
10/25/2025
7:30 PM | |
| Freddie Jackson | City Winery - Chicago
Chicago, IL | Sunday
10/26/2025
7:00 PM | |
| The Psychology of Cults | City Winery - Chicago
Chicago, IL | Tuesday
10/28/2025
7:30 PM | |
| Karyn White | City Winery - Chicago
Chicago, IL | Wednesday
10/29/2025
7:30 PM | |
| My Cousin Tiera | City Winery - Chicago
Chicago, IL | Friday
10/31/2025
6:00 PM | |
| My Cousin Tiera | City Winery - Chicago
Chicago, IL | Friday
10/31/2025
9:30 PM | |
| Cold | City Winery - Chicago
Chicago, IL | Sunday
11/2/2025
7:00 PM | |
| Chante Moore | City Winery - Chicago
Chicago, IL | Monday
11/3/2025
7:30 PM | |
| Chante Moore | City Winery - Chicago
Chicago, IL | Tuesday
11/4/2025
7:30 PM | |
| Chante Moore | City Winery - Chicago
Chicago, IL | Wednesday
11/5/2025
7:30 PM | |
| Norman Brown | City Winery - Chicago
Chicago, IL | Saturday
11/8/2025
6:00 PM | |
| Norman Brown | City Winery - Chicago
Chicago, IL | Saturday
11/8/2025
9:30 PM | |
| The English Beat | City Winery - Chicago
Chicago, IL | Monday
11/10/2025
7:30 PM | |
| The English Beat | City Winery - Chicago
Chicago, IL | Tuesday
11/11/2025
7:30 PM | |
| Patti Austin | City Winery - Chicago
Chicago, IL | Wednesday
11/12/2025
7:30 PM | |
| Patti Austin | City Winery - Chicago
Chicago, IL | Thursday
11/13/2025
7:30 PM | |
| Boney James | City Winery - Chicago
Chicago, IL | Saturday
11/15/2025
6:00 PM | |
| BoDeans | City Winery - Chicago
Chicago, IL | Friday
11/28/2025
7:30 PM | |
| BoDeans | City Winery - Chicago
Chicago, IL | Saturday
11/29/2025
8:30 PM | |
| Michael McDermott | City Winery - Chicago
Chicago, IL | Sunday
12/21/2025
7:00 PM | |
