| Event | Venue | Date/Time | |
| The LadyGang: LadyHang Brunch Club | City Winery - Chicago
Chicago, IL | Saturday
7/11/2026
12:00 PM |  |
| Hip Hop and R&B Bingo With Tom Swoope | City Winery - Chicago
Chicago, IL | Saturday
7/11/2026
9:30 PM | |
| Miss Elli's Groovy Kids Brunch | City Winery - Chicago
Chicago, IL | Sunday
7/12/2026
11:00 AM | |
| Miki Howard | City Winery - Chicago
Chicago, IL | Sunday
7/12/2026
7:00 PM | |
| Souls of Mischief | City Winery - Chicago
Chicago, IL | Monday
7/13/2026
7:30 PM | |
| Just Fine - Mary J. Blige Tribute Band | City Winery - Chicago
Chicago, IL | Tuesday
7/14/2026
7:30 PM | |
| Hip Hop Unplugged | City Winery - Chicago
Chicago, IL | Wednesday
7/15/2026
7:30 PM | |
| Jill Andrews | City Winery - Chicago
Chicago, IL | Thursday
7/16/2026
7:30 PM | |
| John Violinist | City Winery - Chicago
Chicago, IL | Friday
7/17/2026
6:00 PM | |
| John Violinist | City Winery - Chicago
Chicago, IL | Friday
7/17/2026
9:30 PM | |
| Challenge Mania Live | City Winery - Chicago
Chicago, IL | Saturday
7/18/2026
12:00 PM | |
| Elizabeth Brunot | City Winery - Chicago
Chicago, IL | Saturday
7/18/2026
8:00 PM | |
| Spellbinder Magic and Hip Hop Theater Brunch | City Winery - Chicago
Chicago, IL | Sunday
7/19/2026
12:00 PM | |
| David Cook | City Winery - Chicago
Chicago, IL | Sunday
7/19/2026
7:00 PM | |
| Ta'Rhonda Jones | City Winery - Chicago
Chicago, IL | Monday
7/20/2026
7:30 PM | |
| Keiko Matsui | City Winery - Chicago
Chicago, IL | Tuesday
7/21/2026
7:30 PM | |
| Suzie Toot | City Winery - Chicago
Chicago, IL | Wednesday
7/22/2026
7:30 PM | |
| AJ Ghent | City Winery - Chicago
Chicago, IL | Thursday
7/23/2026
7:30 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Friday
7/24/2026
7:30 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Saturday
7/25/2026
4:00 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Saturday
7/25/2026
7:30 PM | |
| Nephew Tommy | City Winery - Chicago
Chicago, IL | Sunday
7/26/2026
4:00 PM | |
| Simply The Best - Tina Turner Tribute | City Winery - Chicago
Chicago, IL | Monday
7/27/2026
7:30 PM | |
| Vernard | City Winery - Chicago
Chicago, IL | Tuesday
7/28/2026
7:30 PM | |
| Lady Bunny Butchers Broadway | City Winery - Chicago
Chicago, IL | Wednesday
7/29/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Thursday
7/30/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Friday
7/31/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Saturday
8/1/2026
7:30 PM | |
| Eric Roberson | City Winery - Chicago
Chicago, IL | Sunday
8/2/2026
7:30 PM | |
| Babatunde HipHopera | City Winery - Chicago
Chicago, IL | Monday
8/3/2026
7:30 PM | |
| Phyllis Yvonne Stickney | City Winery - Chicago
Chicago, IL | Tuesday
8/4/2026
7:30 PM | |
| GLC | City Winery - Chicago
Chicago, IL | Wednesday
8/5/2026
7:30 PM | |
| T.K. Kirkland | City Winery - Chicago
Chicago, IL | Thursday
8/6/2026
7:30 PM | |
| Melanie Fiona | City Winery - Chicago
Chicago, IL | Friday
8/7/2026
6:00 PM | |
| Melanie Fiona | City Winery - Chicago
Chicago, IL | Friday
8/7/2026
9:30 PM | |
| R&B Brunch | City Winery - Chicago
Chicago, IL | Saturday
8/8/2026
12:00 PM | |
| Glenn Jones | City Winery - Chicago
Chicago, IL | Saturday
8/8/2026
5:00 PM | |
| D'Lai | City Winery - Chicago
Chicago, IL | Saturday
8/8/2026
7:30 PM | |
| Lisa Knowles Smith | City Winery - Chicago
Chicago, IL | Sunday
8/9/2026
7:00 PM | |
| Jac Ross | City Winery - Chicago
Chicago, IL | Monday
8/10/2026
7:30 PM | |
| Mohini Dey | City Winery - Chicago
Chicago, IL | Tuesday
8/11/2026
6:00 PM | |
| Mohini Dey | City Winery - Chicago
Chicago, IL | Tuesday
8/11/2026
9:30 PM | |
| Bebel Gilberto | City Winery - Chicago
Chicago, IL | Wednesday
8/12/2026
7:30 PM | |
| Trey Daniels | City Winery - Chicago
Chicago, IL | Thursday
8/13/2026
7:30 PM | |
| J. Holiday | City Winery - Chicago
Chicago, IL | Friday
8/14/2026
7:30 PM | |
| Kenyon Dixon | City Winery - Chicago
Chicago, IL | Saturday
8/15/2026
7:00 PM | |
| Gary Thomas: Sinatra Brunch | City Winery - Chicago
Chicago, IL | Sunday
8/16/2026
12:00 PM | |
| Christian Johnson | City Winery - Chicago
Chicago, IL | Sunday
8/16/2026
7:00 PM | |
| Joyce Hurley | City Winery - Chicago
Chicago, IL | Tuesday
8/18/2026
7:30 PM | |
| The Voice and the Fire - A Tribute to Whitney Houston and Chaka Khan | City Winery - Chicago
Chicago, IL | Wednesday
8/19/2026
7:30 PM | |
| Android Paranoid - Tribute to Radiohead | City Winery - Chicago
Chicago, IL | Thursday
8/20/2026
7:30 PM | |
| Esperanza Spalding | City Winery - Chicago
Chicago, IL | Friday
8/21/2026
7:30 PM | |
| Esperanza Spalding | City Winery - Chicago
Chicago, IL | Saturday
8/22/2026
7:30 PM | |
| Esperanza Spalding | City Winery - Chicago
Chicago, IL | Sunday
8/23/2026
7:00 PM | |
| Neo Soul Love - Tribute to Erykah Badu and Jill Scott | City Winery - Chicago
Chicago, IL | Monday
8/24/2026
7:30 PM | |
| Sapphira Cristal | City Winery - Chicago
Chicago, IL | Tuesday
8/25/2026
7:30 PM | |
| Kofi B | City Winery - Chicago
Chicago, IL | Thursday
8/27/2026
7:30 PM | |
| Goapele | City Winery - Chicago
Chicago, IL | Saturday
8/29/2026
5:00 PM | |
| Goapele | City Winery - Chicago
Chicago, IL | Saturday
8/29/2026
8:30 PM | |
| Monique Renee - Tribute to Teena Marie | City Winery - Chicago
Chicago, IL | Sunday
8/30/2026
12:00 PM | |
| O-Town | City Winery - Chicago
Chicago, IL | Sunday
8/30/2026
7:00 PM | |
| Travis Malloy and Urban Worship Collective | City Winery - Chicago
Chicago, IL | Monday
8/31/2026
7:30 PM | |
| Vibes Live Chicago: A Stepper's Celebration - All White Affair | City Winery - Chicago
Chicago, IL | Tuesday
9/1/2026
7:30 PM | |
| Lyfe Jennings | City Winery - Chicago
Chicago, IL | Thursday
9/3/2026
7:30 PM | |
| Lyfe Jennings | City Winery - Chicago
Chicago, IL | Friday
9/4/2026
6:00 PM | |
| Lyfe Jennings | City Winery - Chicago
Chicago, IL | Friday
9/4/2026
9:30 PM | |
| Christopher Williams | City Winery - Chicago
Chicago, IL | Sunday
9/6/2026
5:00 PM | |
| Christopher Williams | City Winery - Chicago
Chicago, IL | Sunday
9/6/2026
8:30 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Monday
9/7/2026
6:00 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Monday
9/7/2026
9:30 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Tuesday
9/8/2026
6:00 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Tuesday
9/8/2026
9:30 PM | |
| Aja Monet | City Winery - Chicago
Chicago, IL | Wednesday
9/9/2026
5:00 PM | |
| Aja Monet | City Winery - Chicago
Chicago, IL | Wednesday
9/9/2026
8:30 PM | |
| The LeVert Experience | City Winery - Chicago
Chicago, IL | Thursday
9/10/2026
7:30 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Friday
9/11/2026
6:00 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Friday
9/11/2026
9:30 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Saturday
9/12/2026
6:00 PM | |
| Musiq Soulchild | City Winery - Chicago
Chicago, IL | Saturday
9/12/2026
9:30 PM | |
| Lacey Sturm | City Winery - Chicago
Chicago, IL | Sunday
9/13/2026
7:00 PM | |
| Daley | City Winery - Chicago
Chicago, IL | Friday
9/18/2026
7:30 PM | |
| Daley | City Winery - Chicago
Chicago, IL | Saturday
9/19/2026
7:30 PM | |
| Twista with Live Band | City Winery - Chicago
Chicago, IL | Monday
9/21/2026
7:30 PM | |
| Freddie Jackson | City Winery - Chicago
Chicago, IL | Friday
9/25/2026
7:30 PM | |
| Zo! & Tall Black Guy | City Winery - Chicago
Chicago, IL | Tuesday
9/29/2026
7:30 PM | |
| Chris Klemens | City Winery - Chicago
Chicago, IL | Tuesday
10/6/2026
7:30 PM | |
| Santiago Cruz | City Winery - Chicago
Chicago, IL | Wednesday
10/7/2026
7:30 PM | |
| Martin Sexton | City Winery - Chicago
Chicago, IL | Friday
10/9/2026
6:00 PM | |
| Martin Sexton | City Winery - Chicago
Chicago, IL | Friday
10/9/2026
9:30 PM | |
| Rakim | City Winery - Chicago
Chicago, IL | Wednesday
10/14/2026
6:00 PM | |
| Rakim | City Winery - Chicago
Chicago, IL | Wednesday
10/14/2026
9:30 PM | |
| Bob Schneider | City Winery - Chicago
Chicago, IL | Friday
10/16/2026
7:30 PM | |
| Emma Nissen | City Winery - Chicago
Chicago, IL | Monday
10/19/2026
7:30 PM | |
| Davide De Pierro | City Winery - Chicago
Chicago, IL | Wednesday
10/21/2026
7:30 PM | |
| Davide De Pierro | City Winery - Chicago
Chicago, IL | Thursday
10/22/2026
7:30 PM | |
| Michael Jackson's Thriller Live: A Halloween Special | City Winery - Chicago
Chicago, IL | Thursday
10/29/2026
7:30 PM | |
| Joshua Radin | City Winery - Chicago
Chicago, IL | Saturday
11/7/2026
7:30 PM | |
| Joshua Radin | City Winery - Chicago
Chicago, IL | Sunday
11/8/2026
7:00 PM | |
| Griffin House | City Winery - Chicago
Chicago, IL | Monday
12/7/2026
7:30 PM | |
| D.L. Hughley | City Winery - Chicago
Chicago, IL | Friday
12/18/2026
6:00 PM | |
