Stadium: Court 1 Round: 28 Ground: Hardcourt outdoor
| 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 |
| Challenger Chicago MD | 2023/07/13 22:45 | Harrison/Michelsen v Bolt/Uchiyama | 7-6,7-6 |
| Challenger Chicago MD | 2023/07/12 21:30 | Harrison/Michelsen v Lajal/Shelbayh | 6-4,6-4 |