| $200,000 | The Philanthropy Roundtable | Cristo Rey San Jose High School | 2020-12 | Simon prize award |
| $66,500 | The Chicago Community Trust | Kingswood Oxford School | 2020-09 | General operating support |
| $21,000 | The Chicago Community Trust | Kingswood Oxford School | 2023-09 | General operating support |
| $░░░░░ | The Chicago Community Trust | George School | ░░░░-░░ | ░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | De Lasalle Institute | ░░░░-░░ | ░░░░░░░ ░░░░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | St Patrick High School | ░░░░-░░ | ░░░░░░░░░░ ░░░░░░ ░░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | Bishop School | ░░░░-░░ | ░░░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | Kingswood Oxford School | ░░░░-░░ | ░░ ░░░░░░░░░ ░░ |
| $░░░░░ | The Chicago Community Trust | Groton School | ░░░░-░░ | ░░░░░░░░ ░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | Rivers School Corporation | ░░░░-░░ | ░░ ░░░░░░░░░░ ░░░░░░░░ ░░░░░ |
| $░░░░░ | The Chicago Community Trust | Lake Forest Academy (LFA) | ░░░░-░░ | ░░ |
| $░░░░░ | The Chicago Community Trust | Lake Forest Academy (LFA) | ░░░░-░░ | ░░░░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | Lake Forest Academy (LFA) | ░░░░-░░ | ░░░░░ |
| $░░░░░ | The Chicago Community Trust | Lake Forest Academy (LFA) | ░░░░-░░ | ░░ ░░ |
| $░░░░░ | The Chicago Community Trust | Lake Forest Academy (LFA) | ░░░░-░░ | ░░░░░░ ░░░░░░ ░░░░░ ░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | Lake Forest Academy (LFA) | ░░░░-░░ | ░░░░░░░ ░░░░░░░░ ░░░ ░░░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | San Miguel Febres Cordero School | ░░░░-░░ | ░░░░░░░ ░░░░ |
| $░░░░░ | The Chicago Community Trust | San Miguel Febres Cordero School | ░░░░-░░ | ░░░░░░░░ ░░░░░ ░░░░░░░░░░ ░░ |
| $░░░░░ | The Chicago Community Trust | San Miguel Febres Cordero School | ░░░░-░░ | ░░░░░░░ ░░░░░ ░░░░░░ ░░ |
| $░░░░░ | The Chicago Community Trust | San Miguel Febres Cordero School | ░░░░-░░ | ░░░░░░░ ░░░░ ░░ |
| $░░░░░ | The Chicago Community Trust | The Putney School | ░░░░-░░ | ░░░░ ░░░░░░░ ░░░░░░░░░ |
| $░░░░░ | The Chicago Community Trust | The Putney School | ░░░░-░░ | ░░░░░░░ ░░░ ░░░░░░░░░░ ░░░░░ |
| $░░░░░ | The Chicago Community Trust | Wheaton Academy (WA) | ░░░░-░░ | ░░ |
| $░░░░░ | The Chicago Community Trust | Wheaton Academy (WA) | ░░░░-░░ | ░░░░░░░░░ ░░░░ ░░░░░░░░ ░░░░░░ |
| $░░░░░ | The Chicago Community Trust | Wheaton Academy (WA) | ░░░░-░░ | ░░░░░░░░ ░░░░░░░░░░ |