| 1 | Accenture United States Benefit Chicago | $901.3M | $901.3M | $123.3M |
| 2 | Kraft Foods Global INC Retiree Health and Life Benefit Tr Chicago | $553.3M | $82.3M | $791.3M |
| 3 | United Airlines Employee Sick Leave Tr Chicago | $539.7M | $539.7M | $61.6M |
| 4 | Chicago & Vicinity Laborers Distrct Cncil Retire Health & Welfare Plan Westchester | $312.9M | $141.4M | $771.1M |
| 5 | Pepco Holdings INC Veba Trust Chicago | $247.0M | $34.4M | $331.7M |
| 6 | United Airlines Pilot Retiree Health Account Plan Chicago | $211.6M | $191.2M | $953.0M |
| 7 | SEIU Healthcare Il Home Care & Child Care Fund Chicago | $180.8M | $155.1M | $277.2M |
| 8 | Coca-cola Co Postretireme Medical Voluntary Emp Beneficiary Chicago | $145.6M | $28.4M | $41K |
| 9 | Kskj Life Catholic Union Joliet | $134.2M | $104.4M | $547.1M |
| 10 | Clara Abbott Foundation Abbott Park | $67.2M | $0 | $224.1M |
| 11 | University of Chicago Self Insurance Trust Chicago | $66.4M | $61.0M | $288.6M |
| 12 | University of Chicago Retiree Medical Tr Chicago | $59.8M | $39.8M | $122.5M |
| 13 | Komatsu America Corp Retiree Welfare Collectively Bargained Tru Chicago | $57.9M | $4.4M | $49.6M |
| 14 | Bot Chicago Painters & Decorators Retiree Welfare Fund Darien | $51.6M | $10.8M | $160.3M |
| 15 | Ipers Galleria North Tower I INC Chicago | $46.4M | -$26.2M | $1.9M |
| 16 | North Central Illinois Laborers Health & Welfare Fund Peoria | $41.2M | $29.2M | $52.8M |
| 17 | University of Missouri Medical Professional Liability Tr Chicago | $36.3M | $22.3M | $70.2M |
| 18 | United Airlines Technicians and Related Employees Hra&rha Plans Chicago | $31.8M | $31.8M | $51.4M |
| 19 | Childrens Memorial Hospital Self Chicago | $23.7M | $23.7M | $184.4M |
| 20 | Komatsu America Corp Retiree Welfare Noncollectively Bargained Chicago | $23.3M | $3.6M | $25.7M |
| 21 | Trust Agreement of the Retiree Medical Plan of the Plumbers Chicago | $21.7M | $16.0M | $66.3M |
| 22 | Intl Un of Operating Engrs Local 399 Health Reimbursement Account Chicago | $17.0M | $10.7M | $45.9M |
| 23 | Western Area School Employee Benefits Trust Macomb | $16.9M | $16.9M | $1.7M |
| 24 | Rubicon Insurance Company Evanston | $16.2M | $8.3M | $45.8M |
| 25 | Randhill Park Cemetery Assn INC Care Fund Arlington Hts | $16.2M | $14.6M | $80.8M |
| 26 | IBEW Local 134-NECA Vacation Savings Trust Fund Chicago | $16.0M | $16.0M | $3.3M |
| 27 | Chicago Truck Drivers Hlprs & Whse Chicago | $15.3M | $15.3M | $35.8M |
| 28 | Dana Non-union Retiree Veba Trust Chicago | $14.7M | $4.1M | $40.0M |
| 29 | Visionary Schools Tr Schaumburg | $12.4M | $12.4M | $980K |
| 30 | Plan a Health Care Plan Tr Galesburg | $10.2M | $10.2M | $1.7M |
| 31 | Local 309 IBEW Income Security Fund Collinsville | $9.8M | $3.4M | $14.8M |
| 32 | Tr 3500 Maple Corp. Chicago | $8.9M | $312K | $94.6M |
| 33 | Cement Masons Local No 502 Retiree Welfare Fund Bellwood | $8.2M | $6.6M | $18.3M |
| 34 | National Allied Workers Union Insurance Trust Chicago | $7.3M | $7.3M | $6.3M |
| 35 | Black Hawk College Health Benefit Plan Tr Moline | $7.2M | $7.2M | $1.5M |
| 36 | Ipers Rivergate INC Chicago | $6.4M | $6.4M | $74.1M |
| 37 | Neca-ibew Local 364 Supplemental Unemployment Benefit Plan Rockford | $6.1M | $2.3M | $11.1M |
| 38 | Alfa International Global Legal Network INC Chicago | $4.8M | $4.0M | $5.0M |
| 39 | Area Teamsters Insurance Benefit Pl Lyons | $4.5M | $4.5M | $1.8M |
| 40 | Ipers Hamilton Marketplace INC Chicago | $4.4M | $4.4M | $68.4M |
| 41 | Kelly General Construction Company of Decatur INC Benefit Tr Decatur | $3.9M | $3.9M | $189K |
| 42 | Operative Plasterers and Cement Masones International Assoc Local1 Schaumburg | $3.9M | $3.9M | $4.0M |
| 43 | Masonic Association of Evanston Chicago | $3.8M | $127K | $1.2M |
| 44 | Ipers South Loop Market INC Chicago | $3.8M | $3.8M | $42.6M |
| 45 | Village of Schaumburg Veba Health Savings Plan Schaumburg | $3.7M | $1.7M | $8.4M |
| 46 | Japanese Mutual Aid Society of Chicago Chicago | $3.4M | $89K | $1.3M |
| 47 | Retired Teachers Association of Chicago Chicago | $3.3M | $1.0M | $9.7M |
| 48 | Illinois Retired Teachers Association INC Springfield | $3.2M | $1.9M | $4.7M |
| 49 | Bcbssc Voluntary Employees Beneficiary Association Chicago | $2.8M | $584K | $15.7M |
| 50 | Gateway Regional Water Company INC Sandoval | $2.5M | $2.5M | $18.7M |