| AMERICAN COLLEGE OF SURGEONS PROFESSIONA | Chicago | S41 Community Improvement & Capacity Building | $23.5M | 2 |
| AMERICAN BOARD OF MEDICAL SPECIALTIES | Chicago | — | $23.4M | 16 |
| CEFS ECONOMIC OPPORTUNITY CORPORATION | Effingham | P200 Human Services | $23.4M | 3 |
| WEC Energy Group Inc Retiree | Chicago | — | $23.4M | 1 |
| Christian Community Health Center | Chicago | T70Z Philanthropy, Voluntarism & Grantmaking Foundations | $23.3M | 5 |
| UKRAINE-MOLDOVA AMERICAN ENTERPRISE FUND | Chicago | Q32 International, Foreign Affairs & National Security | $23.3M | 6 |
| CONDUIT FOUNDATION | Chicago | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $23.3M | 0 |
| THE DUPAGE COMMUNITY FOUNDATION | Downers Grove | T31 Philanthropy, Voluntarism & Grantmaking Foundations | $23.3M | 4 |
| AWANA CLUBS INTERNATIONAL AND AFFILIATES | St Charles | X200 Religion-Related | $23.3M | 12 |
| BLESSING CORPORATE SERVICES INC | Quincy | E21 Health Care | $23.3M | 11 |
| AMERICAN ASSOCIATION OF ORAL AND | Rosemont | — | $23.2M | 23 |
| EMBARRAS RIVER BASIN AGENCY INC | Greenup | S200 Community Improvement & Capacity Building | $23.2M | 2 |
| LIUNA CHICAGOLAND LABORERS' DISTRICT | Carol Stream | — | $23.1M | 6 |
| Construction Industry Welfare Fund | Rockford | — | $23M | 4 |
| M J M ELECTRIC COOPERATIVE INC | Carlinville | — | $22.9M | 17 |
| SGA Youth & Family Services NFP | Chicago | P20 Human Services | $22.9M | 3 |
| HUMAN SERVICE CENTER | Urbana | F30Z Mental Health & Crisis Intervention | $22.8M | 13 |
| INTERFAITH AMERICA | Chicago | X90 Religion-Related | $22.8M | 14 |
| The Cara Program | Chicago | J200 Employment | $22.8M | 8 |
| UNITED ASSOCIATION OF JOURNEYMEN & | Chicago | — | $22.8M | 33 |
| The University of Chicago Charter School Corporation | Chicago | B20 Education | $22.8M | 12 |
| XS Tennis and Education Foundation | Chicago | N66 Recreation & Sports | $22.7M | 1 |
| PRAIRIE STATE LEGAL SERVICES INC | Rockford | I80Z Crime & Legal-Related | $22.7M | 7 |
| AMERICAN MASSAGE THERAPY ASSOCIATION | Evanston | — | $22.7M | 23 |
| ILLINOIS BANKERS GROUP INSURANCE TRUST | Springfield | — | $22.7M | 1 |
| CHICAGO HOUSE & SOCIAL SERVICE AGENCY | Chicago | G810 Diseases, Disorders & Medical Disciplines | $22.7M | 5 |
| ACCREDITATION ASSOCIATION FOR AMBULATORY | Deerfield | — | $22.7M | 22 |
| CHICAGO LOW INCOME HOUSING TRUST FUND | Chicago | L200 Housing & Shelter | $22.6M | 1 |
| FOREFRONT | Chicago | T50Z Philanthropy, Voluntarism & Grantmaking Foundations | $22.6M | 7 |
| THE CANNING FOUNDATION | Chicago | — | $22.5M | 0 |
| Girl Scouts of Greater Chicago and Northwest Indiana | Chicago | O42 Youth Development | $22.5M | 6 |
| TIMOTHY PLACE NFP | Tinley Park | P75 Human Services | $22.5M | 8 |
| Ace Hardware Foundation | Oak Brook | — | $22.5M | 0 |
| DAY CARE RESOURCES INC | Pekin | — | $22.5M | 2 |
| LABORERS' INT'L UNION OF NORTH AMERICA | Burr Ridge | — | $22.4M | 17 |
| IRONWORKERS LOCAL 395 TRUST FUND | Oak Brook | — | $22.3M | 2 |
| INSTITUTE FOR LATINO PROGRESS | Chicago | P800 Human Services | $22.2M | 7 |
| SINNISSIPPI CENTERS INC | Dixon | F320 Mental Health & Crisis Intervention | $22.1M | 7 |
| Timothy Christian Schools | Elmhurst | — | $22.1M | 8 |
| Springfield Urban League Inc | Springfield | — | $22M | 1 |
| ELEVEN ELEVEN FOUNDATION | Highland Park | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $22M | 1 |
| Lycee Francais de Chicago Inc | Chicago | B99Z Education | $21.9M | 7 |
| SKAGGS FOUNDATION FOR RESEARCH | Chicago | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $21.8M | 2 |
| TAWANI CHARITABLE DISTRIBUTION FUND | Chicago | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $21.7M | 0 |
| PROJECT HOOD COMMUNITY DEVELOPMENT | Chicago | S20 Community Improvement & Capacity Building | $21.6M | 2 |
| EARTHMOVER CREDIT UNION | Aurora | — | $21.6M | 11 |
| WILLIAM NEAL REYNOLDS RESIDUARY TRUST DTD | Chicago | — | $21.6M | 3 |
| ILLINOIS MASONIC CHARITIES FUND | Springfield | B820 Education | $21.6M | 2 |
| Government Finance Officers Association | Chicago | W22C Public & Societal Benefit | $21.6M | 9 |
| COMMUNITY HOSPITAL OF STAUNTON | Staunton | E22Z Health Care | $21.6M | 9 |
