Chicago 
Transfers
| Date | Player | From team | To team | Transfer fee |
|---|---|---|---|---|
| may 7 2024 |  M. Rubiales |  Pims Hairpiece | Chicago (On loan) | (RSD60 731) |
| may 4 2024 | J. Ringer | Chicago | None | RSD26 239 |
| may 4 2024 |  K. Gęsicki | Pims Hairpiece | Chicago | RSD6 693 952 |
| march 10 2024 | K. Gearing | Chicago | None | RSD14 949 |
| january 28 2024 | K. Cowen | William Penn FC | Chicago | RSD6 237 371 |
| january 25 2024 | S. Sletyn | Polar Bear Council FC | Chicago (On loan) | (RSD402 680) |
| january 21 2024 | B. Zane | Chicago | None | RSD34 415 |
| january 18 2024 | J. Esplana | Chicago | None | RSD31 257 |
| december 6 2023 | F. Coulthard | Colonials FC | Chicago (On loan) | (RSD529 551) |
| november 28 2023 | J. Wągrowski | Pims Hairpiece | Chicago | RSD303 277 |
| november 27 2023 | E. Wolford | Chicago | None | RSD22 277 |
| november 6 2023 |  D. Cote | Chicago | None | RSD879 916 |
| november 5 2023 | B. Blank | Columbus Hardworkers | Chicago | RSD23 369 977 |
| november 4 2023 | F. Lázaro | Chicago | None | RSD70 653 |
| october 13 2023 |  P. Niniadis | Pittsburgh Riverhounds | Chicago (On loan) | (RSD482 901) |
| september 13 2023 | Z. Tarbox | Chicago | None | RSD50 586 |
| august 21 2023 | S. Aroya | MXL Luneng Taishan | Chicago (On loan) | (RSD129 173) |
| july 25 2023 | E. Thorne | Chicago | None | RSD21 863 |
| june 30 2023 | M. Arguedas | MXL Luneng Taishan | Chicago (On loan) | (RSD126 857) |
| june 25 2023 | R. Ebbert | Chicago | None | RSD740 514 |
| june 24 2023 | Y. Yee | Chicago | None | RSD27 479 |
| june 1 2023 | S. Palmer | Chicago | None | RSD845 499 |
| may 12 2023 |  H. Tesfaye | Legends SC | Chicago (On loan) | (RSD129 102) |
| january 29 2023 | H. Covey |  FC Port Vila | Chicago (On loan) | (RSD828 201) |
| january 22 2023 | T. McDaniels | Chicago | None | RSD10 000 |