| Show | Your Voice Chicago |
| Issa Rae | ... | Jamele Demmings |
| Maya Rudolph | ... | Caviar |
| Beck Bennett | ... | Scott Trebor Still |
| Heidi Gardner | ... | Catherine Lacy Still |
| Punkie Johnson | ... | Crystal |
| Ego Nwodim | ... | Lisa Crowder |
| Chris Redd | ... | Reverend D'Angelo Banks |
| Kenan Thompson | ... | J. Louis Tibbs |
| Bowen Yang | ... | Daniel Lee Still |
| Gary Richardson | ... | Rashad Carter Still |