| USA USL League Two | 2022/07/16 23:00 | Springfield ASC v Chicago City SC | W | 1-4 |
| USA USL League Two | 2022/07/14 00:00 | Chicago City SC v St Louis Lions | D | 3-3 |
| USA USL League Two | 2022/07/07 00:00 | Chicago City SC v Chicago FC United | L | 2-4 |
| USA USL League Two | 2022/07/03 23:00 | Chicago City SC v Springfield ASC | W | 4-2 |
| USA USL League Two | 2022/07/02 00:00 | Chicago FC United v Chicago City SC | L | 1-0 |
| USA USL League Two | 2022/06/30 00:00 | Chicago Dutch Lions v Chicago City SC | W | 3-5 |
| USA USL League Two | 2022/06/26 00:30 | Kaw Valley FC v Chicago City SC | L | 2-0 |
| USA USL League Two | 2022/06/25 00:00 | FC Wichita v Chicago City SC | L | 3-1 |