| THE HOPE SCHOOL | Springfield | B280 Education | $33.1M | 5 |
| UNIVERSITY CLUB OF CHICAGO | Chicago | — | $32.8M | 9 |
| WASHINGTON AND JANE SMITH COMMUNITY - | Orland Park | L220 Housing & Shelter | $32.8M | 4 |
| INTRINSIC SCHOOLS | Chicago | B29 Education | $32.7M | 6 |
| University of Chicago Self Insurance Trust | Chicago | Y200 Mutual & Membership Benefit | $32.6M | 0 |
| UFCW L1546 FOOD HANDLERS WELFARE FUND | Oakbrook | — | $32.5M | 0 |
| PAWS CHICAGO | Chicago | D200 Animal-Related | $32.4M | 8 |
| PERSPECTIVES CHARTER SCHOOLS | Chicago | B25Z Education | $32.2M | 6 |
| THE MATHER EVANSTON | Evanston | P75 Human Services | $31.9M | 8 |
| Center for Housing and Health | Chicago | L99 Housing & Shelter | $31.9M | 2 |
| ACADEMY FOR GLOBAL CITIZENSHIP | Chicago | B29 Education | $31.8M | 4 |
| CHALLENGE UNLIMITED INC | Alton | J30Z Employment | $31.8M | 7 |
| PAINTERS DISTRICT COUNCIL NO 30 | Aurora | — | $31.7M | 5 |
| IRONWORKERS TRI-STATE WELFARE PLAN | Schaumburg | — | $31.6M | 6 |
| Catalyst Schools | Chicago | B240 Education | $31.6M | 7 |
| MEDINAH COUNTRY CLUB | Medinah | — | $31.5M | 11 |
| COLES-MOULTRIE ELECTRIC COOPERATIVE | Mattoon | — | $31.5M | 13 |
| PIPE FITTERS TRAINING | Mokena | — | $31.5M | 7 |
| CHARLES W & PATRICIA S BIDWILL | Chicago | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $31.4M | 1 |
| NECA IBEW 176 HEALTH & WELFARE FUND | Joliet | — | $31.4M | 3 |
| AGENCY FOR COMMUNITY TRANSIT | Pontoon Beach | P52Z Human Services | $31.2M | 12 |
| AISC HOLDINGS INC | Chicago | — | $31.1M | 7 |
| LOCAL UNION NO 9 IBEW & OUTSIDE | Tinley Park | — | $31M | 5 |
| CTF ILLINOIS | Orland Park | L99 Housing & Shelter | $31M | 4 |
| CEMENT MASONS INSTITUTE LOCAL 502 | Bellwood | — | $31M | 12 |
| Near North Health Service Corporation | Chicago | E30 Health Care | $30.9M | 7 |
| LOUISE H NEUHOFF CHARITABLE TRUST AGREEMENT | Chicago | — | $30.9M | 1 |
| McDermott Center | Chicago | — | $30.9M | 9 |
| ONEGOAL | Chicago | O50 Youth Development | $30.8M | 12 |
| LEGAL AID CHICAGO | Chicago | I80Z Crime & Legal-Related | $30.6M | 7 |
| INTERNATIONAL BROTHERHOOD OF ELECTRICAL | Chicago | — | $30.6M | 20 |
| AUTOMATIC SPRINKLER LOCAL 281 UA | Alsip | — | $30.4M | 4 |
| RIVERSIDE SENIOR LIVING CENTER | Kankakee | P75Z Human Services | $30.4M | 10 |
| UCM Care Network Medical Group Inc | Chicago | E21 Health Care | $30.4M | 20 |
| ALLENDALE ASSOCIATION | Lake Villa | — | $30.2M | 8 |
| THE HEKTOEN INSTITUTE OF MEDICINE | Chicago | E05 Health Care | $30.2M | 7 |
| EDER FINANCIAL INC | Elgin | — | $30.1M | 5 |
| SOUTHERN ILLINOIS ELECTRIC COOPERATIVE | Dongola | — | $30.1M | 17 |
| Deaconess Illinois Union County | Anna | E22 Health Care | $30M | 5 |
| NECA-IBEW LOCAL NO 364 | Rockford | — | $30M | 1 |
| LAND OF LINCOLN GOODWILL INDUSTRIES INC | Springfield | J32 Employment | $30M | 5 |
| KANE COUNTY TEACHERS CREDIT UNION | Elgin | — | $29.9M | 7 |
| AMERICAN SOCIETY OF PLASTIC SURGEONS | Arlington Heights | — | $29.8M | 13 |
| Wellness West Inc | Chicago | — | $29.8M | 0 |
| WESTMINSTER VILLAGE INC | Bloomington | P750 Human Services | $29.8M | 7 |
| Heartland Credit Union | Springfield | — | $29.7M | 12 |
| EL VALOR CORPORATION | Chicago | — | $29.7M | 7 |
| JFMC FACILITIES CORPORATION | Chicago | T020 Philanthropy, Voluntarism & Grantmaking Foundations | $29.6M | 8 |
| THE ZAKAT FOUNDATION OF AMERICA | Worth | Z99 Unknown | $29.5M | 5 |
| CHICAGO THEATRE GROUP INC | Chicago | A650 Arts, Culture & Humanities | $29.4M | 9 |
