Chicago II: every transfer in and out, fees paid and earned, squad market value, €250k spent.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2026-01-01 | Harold Osorio | Chicago II | Alianza FC | Free |
| 2025-09-08 | Claudio Cassano | Chicago II | FC Lugano | Loan |
| 2025-02-10 | Claudio Cassano | Cittadella | Chicago II | €250k |
| 2025-01-01 | Lamonth Rochester | Chicago II | Tijuana U23 | — |
| 2024-12-11 | David Poreba | Chicago II | Chicago | — |
| 2024-07-01 | David Poreba | Stal Mielec | Chicago II | Free |
| 2024-02-23 | Jason Shokalook | Chicago | Chicago II | Loan |
| 2024-01-31 | David Poreba | Stal Mielec | Chicago II | Loan |
| 2023-03-30 | Lamonth Rochester | Angelina | Chicago II | Free |
| 2023-01-01 | Justin Reynolds | Chicago II | Chicago | — |
| 2022-08-10 | Harold Osorio | Alianza FC | Chicago II | — |
| 2022-05-12 | Justin Reynolds | Fire Academy | Chicago II | — |
| 2022-03-25 | Noeh Hernández | Fire Academy | Chicago II | Loan |
| 2022-03-25 | Justin Reynolds | Fire Academy | Chicago II | Loan |