Stadium: Center Court Round: 29 Ground: Hardcourt outdoor
| Challenger Chicago MD | 2023/07/14 17:00 | Chung/Harris v Harrison/Sandgren | 6-4,3-6,10-7 |
| Challenger Chicago MD | 2023/07/13 22:20 | Chung/Harris v Shimizu/Sigouin | 2-6,6-3,12-10 |
| Challenger Chicago MD | 2023/07/12 22:50 | Chung/Harris v Schoolkate/Walton | 3-6,6-3,11-9 |
| Challenger Chicago MD | 2023/07/14 23:00 | Libietis/Mansouri v Harrison/Michelsen | 7-6,6-1 |
| Challenger Chicago MD | 2023/07/14 19:45 | Jung/King v Libietis/Mansouri | 7-6,3-6,7-10 |
| Challenger Chicago MD | 2023/07/12 19:30 | Libietis/Mansouri v Raja/Sharan | 6-7,6-2,10-6 |