| Event | Venue | Date/Time | |
| Tim Rogers and The Fellas | City Winery - Chicago Chicago, IL | Monday 11/9/2026 7:30 PM |  |
| Cem Adrian | City Winery - Chicago Chicago, IL | Tuesday 11/10/2026 6:30 PM |  |
| Michelle Collins | City Winery - Chicago Chicago, IL | Wednesday 11/11/2026 7:30 PM |  |
| The Eric Roberson Improv Sessions | City Winery - Chicago Chicago, IL | Thursday 11/12/2026 6:00 PM |  |
| Ami Taf Ra | City Winery - Chicago Chicago, IL | Friday 11/13/2026 6:00 PM |  |
| Ami Taf Ra | City Winery - Chicago Chicago, IL | Friday 11/13/2026 9:30 PM |  |
| Ami Taf Ra | City Winery - Chicago Chicago, IL | Saturday 11/14/2026 6:00 PM |  |
| Ami Taf Ra | City Winery - Chicago Chicago, IL | Saturday 11/14/2026 9:30 PM |  |
| Soul Brunch: A Tribute to Teena Marie & Rick James | City Winery - Chicago Chicago, IL | Sunday 11/15/2026 12:00 PM |  |
| Marcus Veltri & Rob Landes | City Winery - Chicago Chicago, IL | Sunday 11/15/2026 7:00 PM |  |
| Aubrey O'Day | City Winery - Chicago Chicago, IL | Tuesday 11/17/2026 7:30 PM |  |
| Rozzi | City Winery - Chicago Chicago, IL | Wednesday 11/18/2026 7:30 PM |  |
| Wood Harris | City Winery - Chicago Chicago, IL | Thursday 11/19/2026 7:30 PM |  |
| Brother Ali | City Winery - Chicago Chicago, IL | Friday 11/20/2026 7:30 PM |  |
| Boney James | City Winery - Chicago Chicago, IL | Saturday 11/21/2026 5:00 PM |  |
| Boney James | City Winery - Chicago Chicago, IL | Saturday 11/21/2026 8:30 PM |  |
| Boney James | City Winery - Chicago Chicago, IL | Sunday 11/22/2026 5:00 PM |  |
| Boney James | City Winery - Chicago Chicago, IL | Sunday 11/22/2026 8:30 PM |  |
| Damon Williams | City Winery - Chicago Chicago, IL | Monday 11/23/2026 7:30 PM |  |
| Mohini Dey | City Winery - Chicago Chicago, IL | Tuesday 11/24/2026 6:00 PM |  |
| Mohini Dey | City Winery - Chicago Chicago, IL | Tuesday 11/24/2026 9:30 PM |  |
| The PC Band | City Winery - Chicago Chicago, IL | Wednesday 11/25/2026 7:30 PM |  |
| Crucial Conflict | City Winery - Chicago Chicago, IL | Friday 11/27/2026 7:30 PM |  |
| The Walls Group | City Winery - Chicago Chicago, IL | Sunday 11/29/2026 7:00 PM |  |
| Cousin Tiera | City Winery - Chicago Chicago, IL | Monday 11/30/2026 7:30 PM |  |
| Mickey Guyton | City Winery - Chicago Chicago, IL | Wednesday 12/2/2026 7:30 PM |  |
| Jubu Smith | City Winery - Chicago Chicago, IL | Saturday 12/5/2026 6:00 PM |  |
| Jubu Smith | City Winery - Chicago Chicago, IL | Saturday 12/5/2026 9:30 PM |  |
| Kurt Elling Sings Christmas | City Winery - Chicago Chicago, IL | Sunday 12/6/2026 5:00 PM |  |
| Kurt Elling Sings Christmas | City Winery - Chicago Chicago, IL | Sunday 12/6/2026 8:30 PM |  |
| Griffin House | City Winery - Chicago Chicago, IL | Monday 12/7/2026 7:30 PM |  |
| Jody Nardone Trio - A Charlie Brown Christmas | City Winery - Chicago Chicago, IL | Tuesday 12/8/2026 7:30 PM |  |
| Damien Escobar | City Winery - Chicago Chicago, IL | Sunday 12/13/2026 5:00 PM |  |
| Damien Escobar | City Winery - Chicago Chicago, IL | Sunday 12/13/2026 8:30 PM |  |
| Glenn Jones | City Winery - Chicago Chicago, IL | Monday 12/14/2026 7:30 PM |  |
| Los Lobos & Backyard Tire Fire | City Winery - Chicago Chicago, IL | Wednesday 12/16/2026 7:30 PM |  |
| Los Lobos & Backyard Tire Fire | City Winery - Chicago Chicago, IL | Thursday 12/17/2026 7:30 PM |  |
| D.L. Hughley | City Winery - Chicago Chicago, IL | Friday 12/18/2026 6:00 PM |  |
| D.L. Hughley | City Winery - Chicago Chicago, IL | Friday 12/18/2026 9:30 PM |  |
| D.L. Hughley | City Winery - Chicago Chicago, IL | Saturday 12/19/2026 6:00 PM |  |
| D.L. Hughley | City Winery - Chicago Chicago, IL | Saturday 12/19/2026 9:30 PM |  |
| D.L. Hughley | City Winery - Chicago Chicago, IL | Sunday 12/20/2026 5:00 PM |  |
| D.L. Hughley | City Winery - Chicago Chicago, IL | Sunday 12/20/2026 8:30 PM |  |
| Michael McDermott | City Winery - Chicago Chicago, IL | Monday 12/21/2026 7:30 PM |  |
| Michael McDermott | City Winery - Chicago Chicago, IL | Tuesday 12/22/2026 7:30 PM |  |
| Michael McDermott | City Winery - Chicago Chicago, IL | Wednesday 12/23/2026 7:30 PM |  |
| Terisa Griffin & Lady Alma | City Winery - Chicago Chicago, IL | Saturday 12/26/2026 7:30 PM |  |
| Ronnie Baker Brooks | City Winery - Chicago Chicago, IL | Saturday 1/2/2027 7:30 PM |  |
| Simone Green | City Winery - Chicago Chicago, IL | Tuesday 1/5/2027 7:30 PM |  |
| Simone Green | City Winery - Chicago Chicago, IL | Wednesday 1/6/2027 7:30 PM |  |
| Elle Varner | City Winery - Chicago Chicago, IL | Thursday 1/7/2027 7:30 PM |  |
| RNB After Dark: Chicago Edition | City Winery - Chicago Chicago, IL | Friday 1/8/2027 7:30 PM |  |
| Aniba and The Sol Starz | City Winery - Chicago Chicago, IL | Wednesday 1/13/2027 7:30 PM |  |
| Najee | City Winery - Chicago Chicago, IL | Friday 1/15/2027 6:00 PM |  |
| Najee | City Winery - Chicago Chicago, IL | Friday 1/15/2027 9:30 PM |  |
| Bobby V. | City Winery - Chicago Chicago, IL | Saturday 1/16/2027 7:30 PM |  |
| Midnight Sun Band ft. Shauntia | City Winery - Chicago Chicago, IL | Sunday 1/17/2027 7:00 PM |  |
| Midnight Sun Band ft. Shauntia | City Winery - Chicago Chicago, IL | Monday 1/18/2027 7:30 PM |  |
| Glenn Lewis & Teni Tinks | City Winery - Chicago Chicago, IL | Tuesday 1/19/2027 7:30 PM |  |
| Smells Like Nirvana - Nirvana Tribute | City Winery - Chicago Chicago, IL | Wednesday 1/20/2027 7:30 PM |  |
| Public Announcement | City Winery - Chicago Chicago, IL | Thursday 1/21/2027 7:30 PM |  |
| Kirk Whalum | City Winery - Chicago Chicago, IL | Saturday 1/23/2027 5:00 PM |  |
| Kirk Whalum | City Winery - Chicago Chicago, IL | Saturday 1/23/2027 8:30 PM |  |
| Raheem DeVaughn | City Winery - Chicago Chicago, IL | Friday 1/29/2027 6:00 PM |  |
| Raheem DeVaughn | City Winery - Chicago Chicago, IL | Friday 1/29/2027 9:30 PM |  |
| Raheem DeVaughn | City Winery - Chicago Chicago, IL | Saturday 1/30/2027 6:00 PM |  |
| Raheem DeVaughn | City Winery - Chicago Chicago, IL | Saturday 1/30/2027 9:30 PM |  |
| Jane Eugene | City Winery - Chicago Chicago, IL | Sunday 1/31/2027 5:00 PM |  |
| Jane Eugene | City Winery - Chicago Chicago, IL | Sunday 1/31/2027 8:30 PM |  |
| Gabriella Lester | City Winery - Chicago Chicago, IL | Wednesday 2/3/2027 7:30 PM |  |
| 10,000 Maniacs | City Winery - Chicago Chicago, IL | Friday 2/5/2027 7:30 PM |  |
| 10,000 Maniacs | City Winery - Chicago Chicago, IL | Saturday 2/6/2027 7:30 PM |  |
| Syleena Johnson | City Winery - Chicago Chicago, IL | Saturday 2/13/2027 6:00 PM |  |
| Syleena Johnson | City Winery - Chicago Chicago, IL | Saturday 2/13/2027 9:30 PM |  |
| Syleena Johnson | City Winery - Chicago Chicago, IL | Sunday 2/14/2027 2:00 PM |  |
| Syleena Johnson | City Winery - Chicago Chicago, IL | Monday 2/15/2027 7:30 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Thursday 2/18/2027 6:00 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Thursday 2/18/2027 9:30 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Friday 2/19/2027 6:00 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Friday 2/19/2027 9:30 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Saturday 2/20/2027 6:00 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Saturday 2/20/2027 9:30 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Sunday 2/21/2027 5:00 PM |  |
| Robert Glasper | City Winery - Chicago Chicago, IL | Sunday 2/21/2027 8:30 PM |  |
| Marcus Miller | City Winery - Chicago Chicago, IL | Saturday 2/27/2027 5:00 PM |  |
| Marcus Miller | City Winery - Chicago Chicago, IL | Saturday 2/27/2027 8:30 PM |  |
| Howard Hewett | City Winery - Chicago Chicago, IL | Sunday 3/7/2027 5:00 PM |  |
| Howard Hewett | City Winery - Chicago Chicago, IL | Sunday 3/7/2027 8:30 PM |  |
| Surabhi Ensemble | City Winery - Chicago Chicago, IL | Monday 3/15/2027 7:30 PM |  |
| Valerie June | City Winery - Chicago Chicago, IL | Sunday 3/21/2027 7:00 PM |  |
| Chrisette Michele | City Winery - Chicago Chicago, IL | Friday 3/26/2027 6:00 PM |  |
| Chrisette Michele | City Winery - Chicago Chicago, IL | Friday 3/26/2027 9:30 PM |  |
| Paris Chansons | City Winery - Chicago Chicago, IL | Thursday 4/1/2027 7:30 PM |  |
| Brandy Clark | City Winery - Chicago Chicago, IL | Sunday 4/11/2027 7:00 PM |  |
| Basketmouth | City Winery - Chicago Chicago, IL | Tuesday 4/13/2027 7:30 PM |  |
| Jason Ladanye | City Winery - Chicago Chicago, IL | Thursday 6/3/2027 7:30 PM |  |