| 1 | Central States Southeast & Southwest Areas Health & Welfare F Chicago | $56.5B | $5.5B | $16.6B |
| 2 | Modern Woodmen of America Rock Island | $1.9B | $1.9B | $18.2B |
| 3 | Unite Here Health Oak Brook | $1.9B | $1.5B | $1.4B |
| 4 | Memorial Health System Springfield | $1.8B | $1.6B | $2.0B |
| 5 | American Medical Association Chicago | $1.7B | $546.2M | $1.5B |
| 6 | Eder Financial INC Elgin | $1.4B | $74.6M | $340.6M |
| 7 | Electrical Insurance Trustees Alsip | $1.4B | $361.1M | $863.3M |
| 8 | Line Construction Benefit Fund Lombard | $1.2B | $1.2B | $1.9B |
| 9 | Delta Dental of Illinois Naperville | $1.0B | $1.0B | $216.3M |
| 10 | Big Ten Conference INC Rosemont | $934.1M | $928.1M | $292.3M |
| 11 | Chicago District Council of Carpenters Welfare Fund Chicago | $860.5M | $432.8M | $1.4B |
| 12 | National Association of Realtors Chicago | $840.0M | $360.8M | $1.1B |
| 13 | Midwest Operating Engineers Welfare Fund Countryside | $822.4M | $801.8M | $2.3B |
| 14 | Elmhurst Memorial Healthcare Arlington Hts | $667.1M | $666.6M | $695.0M |
| 15 | Arie and Ida Crown Memorial Chicago | $622.0M | $0 | $1.4B |
| 16 | Swedish Covenant Health Arlington Hts | $607.5M | $607.5M | $336.2M |
| 17 | Chicago & Vicinity Laborers District Council Health & Welfare Westchester | $591.0M | $263.9M | $680.3M |
| 18 | Exelon Corporation Employees Benefit Trust for Union Employees Chicago | $568.1M | $36.4M | $709.2M |
| 19 | Automobile Mechanics-701 Union and Industry Welfare Fund-trust Burr Ridge | $508.9M | $125.6M | $316.9M |
| 20 | Christian Brothers Employee Benefit Trust Romeoville | $507.3M | $414.4M | $223.5M |
| 21 | The Members Retirement Plan St. Charles | $472.4M | $44.8M | $673.9M |
| 22 | Pipe Fitters Welfare Fund Local 597 Chicago | $403.6M | $195.8M | $342.1M |
| 23 | Ahs Midwest Management INC La Grange | $366.2M | $366.2M | $37.5M |
| 24 | International Fellowship of Christians & Jews Chicago | $354.0M | $318.2M | $233.0M |
| 25 | Exelon Corporation Employees Benefit Trust Chicago | $345.7M | $345.7M | $62.0M |
| 26 | College of American Pathologists Northfield | $329.6M | $299.5M | $400.5M |
| 27 | American Dental Association Chicago | $323.2M | $237.1M | $286.9M |
| 28 | Consumers Power Company Union Welfare Tr to Provide for Retiree Chicago | $318.2M | $14.9M | $868.4M |
| 29 | Cantigny Foundation Chicago Il | $306.1M | $100.2M | $547.0M |
| 30 | Neca-ibew Welfare Trust Fund Decatur | $287.9M | $241.1M | $341.3M |
| 31 | McMaster-carr Supply Co Employees Welfare Tr Elmhurst | $273.8M | $157.5M | $531.4M |
| 32 | Adventist Bolingbrook Hospital Bolingbrook | $255.3M | $255.3M | $285.6M |
| 33 | Consumers Credit Union Lake Forest | $255.3M | $255.3M | $4.0B |
| 34 | SEIU Local 1 & Participating Employers Health Trust Chicago | $246.0M | $150.2M | $171.7M |
| 35 | Caterpillar INC Group Insurance Master Trust Agreement Chicago | $230.8M | $138.6M | $87.8M |
| 36 | Howard Brown Health Center Chicago | $224.4M | $205.0M | $178.5M |
| 37 | Elmhurst University Elmhurst | $219.6M | $0 | $293.3M |
| 38 | Hyatt Corporation Welfare Benefit Trust Chicago | $217.3M | $217.3M | $16.4M |
| 39 | Global Technology Industry Association Downers Grove | $216.9M | $216.9M | $161.1M |
| 40 | Catholic Charities of the Archdiocese of Chicago Chicago | $215.7M | $201.5M | $214.7M |
| 41 | Rosalind Franklin University of Medicine & Science North Chicago | $213.2M | $137.9M | $308.8M |
| 42 | Kraft Foods North America INC Group Benefit Trust I Chicago | $205.5M | $205.5M | $14.9M |
| 43 | Polk Bros Foundation INC Chicago | $198.4M | $0 | $319.3M |
| 44 | Roosevelt University Chicago | $196.6M | $130.4M | $393.3M |
| 45 | Southern Illinois Power Cooperative Marion | $195.1M | $195.0M | $659.2M |
| 46 | Prairie Power INC Springfield | $179.7M | $178.8M | $795.2M |
| 47 | Ih Mississippi Valley Credit Union Moline | $176.8M | $158.2M | $2.2B |
| 48 | Gibson Area Hospital Gibson City | $174.8M | $174.8M | $88.7M |
| 49 | United Brotherhood of Carpenters & Joiners of America Chicago | $169.1M | $110.0M | $262.1M |
| 50 | Dairy Management INC Rosemont | $165.7M | $165.7M | $25.4M |