| 4. Jornada | 22.07.2021 | Chicago Fire | - | D.C. United | 2:2 | ||||
| 5. Jornada | 05.08.2021 | Chicago Fire | - | New York City FC | 0:0 | ||||
| 5. Jornada | 16.08.2021 | Chicago Fire | - | Columbus Crew | 1:0 | ||||
| 5. Jornada | 19.08.2021 | Inter Miami CF | - | Chicago Fire | 3:2 | ||||
| 5. Jornada | 22.08.2021 | Orlando City | - | Chicago Fire | 1:0 | ||||
| 6. Jornada | 12.09.2021 | Sporting Kansas City | - | Chicago Fire | 2:0 | ||||
| 6. Jornada | 16.09.2021 | D.C. United | - | Chicago Fire | 3:0 | ||||
| 6. Jornada | 19.09.2021 | CF Montréal | - | Chicago Fire | 2:0 | ||||
| 7. Jornada | 03.10.2021 | Toronto FC | - | Chicago Fire | 3:1 | ||||
| 7. Jornada | 17.10.2021 | New England Revolution | - | Chicago Fire | 2:2 | ||||
| 8. Jornada | 07.11.2021 | Columbus Crew | - | Chicago Fire | 2:0 |  |
Bulgaria