| 2023-10-21 | New York CityvChicago FireMLS · United States | 1–0 | MLS · United States |
| 2023-10-08 | Chicago FirevCharlotteMLS · United States | 0–2 | MLS · United States |
| 2023-10-05 | Chicago FirevInter MiamiMLS · United States | 4–1 | MLS · United States |
| 2023-10-01 | New York Red BullsvChicago FireMLS · United States | 0–1 | MLS · United States |
| 2023-09-24 | Chicago FirevNew England RevolutionMLS · United States | 2–2 | MLS · United States |
| 2023-09-21 | Columbus CrewvChicago FireMLS · United States | 3–0 | MLS · United States |
| 2023-09-17 | CF MontrealvChicago FireMLS · United States | 0–0 | MLS · United States |
| 2023-09-03 | DC UnitedvChicago FireMLS · United States | 4–0 | MLS · United States |
| 2023-08-31 | Chicago FirevVancouver WhitecapsMLS · United States | 0–1 | MLS · United States |
| 2023-08-27 | Los Angeles GalaxyvChicago FireMLS · United States | 3–0 | MLS · United States |
| 2023-08-21 | Chicago FirevOrlando CityMLS · United States | 1–3 | MLS · United States |
| 2023-07-16 | Chicago FirevToronto FCMLS · United States | 1–0 | MLS · United States |
| 2023-07-13 | Chicago FirevCF MontrealMLS · United States | 3–0 | MLS · United States |
| 2023-07-09 | Chicago FirevNashville SCMLS · United States | 1–0 | MLS · United States |
| 2023-07-02 | Orlando CityvChicago FireMLS · United States | 3–1 | MLS · United States |
| 2023-06-25 | Sporting Kansas CityvChicago FireMLS · United States | 0–1 | MLS · United States |
| 2023-06-22 | Portland TimbersvChicago FireMLS · United States | 1–2 | MLS · United States |
| 2023-06-11 | Chicago FirevColumbus CrewMLS · United States | 1–2 | MLS · United States |
| 2023-06-04 | FC CincinnativChicago FireMLS · United States | 1–0 | MLS · United States |
| 2023-06-01 | Toronto FCvChicago FireMLS · United States | 0–0 | MLS · United States |
| 2023-05-28 | New England RevolutionvChicago FireMLS · United States | 3–3 | MLS · United States |
| 2023-05-21 | Chicago FirevAtlanta UtdMLS · United States | 3–3 | MLS · United States |
| 2023-05-18 | CharlottevChicago FireMLS · United States | 2–1 | MLS · United States |
| 2023-05-13 | Chicago FirevSt. Louis CityMLS · United States | 1–0 | MLS · United States |
| 2023-05-07 | Nashville SCvChicago FireMLS · United States | 3–0 | MLS · United States |
| 2023-04-30 | Chicago FirevNew York Red BullsMLS · United States | 1–1 | MLS · United States |
| 2023-04-23 | Atlanta UtdvChicago FireMLS · United States | 2–1 | MLS · United States |
| 2023-04-16 | Chicago FirevPhiladelphia UnionMLS · United States | 2–2 | MLS · United States |
| 2023-04-09 | Chicago FirevMinnesota UnitedMLS · United States | 2–1 | MLS · United States |
| 2023-04-02 | Chicago FirevDC UnitedMLS · United States | 0–0 | MLS · United States |
| 2023-03-25 | Inter MiamivChicago FireMLS · United States | 2–3 | MLS · United States |
| 2023-03-19 | Chicago FirevFC CincinnatiMLS · United States | 3–3 | MLS · United States |
| 2023-03-12 | Philadelphia UnionvChicago FireMLS · United States | 1–0 | MLS · United States |
| 2023-03-05 | Chicago FirevNew York CityMLS · United States | 1–1 | MLS · United States |