| 51 | Chicago Airlines Terminal Consortium | $44,549,040 | 114 | 2 |
| 52 | Cook County Collector | $43,370,033 | 325 | 1 |
| 53 | Transystems Corporation | $43,249,973 | 142 | 3 |
| 54 | Aecom-Dbs | $42,075,479 | 12 | 1 |
| 55 | Fraternal Order of Police | $41,259,127 | 109 | 1 |
| 56 | John Burns Construction Co. | $39,308,604 | 162 | 3 |
| 57 | Ccmsi | $39,139,111 | 424 | 1 |
| 58 | Genuine Parts Company | $39,005,658 | 272 | 3 |
| 59 | Chicago Parking Meters LLC | $38,762,540 | 13 | 1 |
| 60 | Connect Chicago Alliance JV | $38,586,120 | 450 | 1 |
| 61 | Arthur J Gallagher Risk Management Services LLC | $38,446,944 | 69 | 1 |
| 62 | Studio Ord Inc | $34,706,918 | 173 | 1 |
| 63 | Cnect LLC | $34,100,144 | 58 | 1 |
| 64 | Mat Construction Leasing, Inc. | $33,546,959 | 127 | 2 |
| 65 | Power Rogers, LLP | $33,534,968 | 5 | 1 |
| 66 | T & N Chicago, Inc. | $33,409,844 | 214 | 3 |
| 67 | Reliable Asphalt Corp. | $31,766,543 | 88 | 3 |
| 68 | Pcwp, LLC | $31,584,133 | 13 | 1 |
| 69 | Lakeshore Recycling Systems | $31,462,068 | 60 | 3 |
| 70 | ABM Aviation | $30,891,066 | 13 | 1 |
| 71 | All Chicago Making Homelessness History | $30,363,072 | 299 | 2 |
| 72 | Midway Airlines' Terminal | $29,000,596 | 55 | 1 |
| 73 | Transwestern Commercial Services, LLC. | $28,708,001 | 220 | 2 |
| 74 | Colonial Oil Industries, Inc. | $28,702,234 | 1,142 | 2 |
| 75 | Commonwealth. Edison Co. | $28,447,510 | 3,842 | 1 |
| 76 | HNTB Corporation | $28,357,585 | 277 | 4 |
| 77 | Cbre Inc. | $27,095,733 | 71 | 3 |
| 78 | M.Q. Sewer & Water Contractors | $26,981,871 | 110 | 3 |
| 79 | Granite Construction Company. | $26,957,645 | 101 | 3 |
| 80 | Skyline Management Group O'hare | $26,736,514 | 13 | 1 |
| 81 | Greater Illinois Title Company | $26,499,523 | 169 | 2 |
| 82 | After-School Matters, Inc. | $25,892,664 | 373 | 3 |
| 83 | Kyndryl, Inc. | $25,373,985 | 63 | 1 |
| 84 | Motorola Solutions Inc | $25,369,365 | 117 | 2 |
| 85 | Mansfield Power & Gas, LLC | $25,334,628 | 29 | 1 |
| 86 | Sutton Ford, Inc. | $25,234,318 | 149 | 2 |
| 87 | K-Five Construction Corp./Plote Construction Inc JV | $25,009,305 | 5 | 1 |
| 88 | Open Kitchens, Inc. | $24,132,959 | 124 | 2 |
| 89 | Fire Service Inc | $23,698,120 | 108 | 2 |
| 90 | USAA Annuity Services Corporation | $23,650,000 | 5 | 1 |
| 91 | Rossi Contractors, Inc. | $23,297,741 | 62 | 1 |
| 92 | Midway Management Group JV | $22,995,675 | 36 | 1 |
| 93 | Sotos Law Firm, P.C. | $21,926,262 | 238 | 1 |
| 94 | Rausch Infrastructure LLC | $21,710,045 | 36 | 3 |
| 95 | Seven D Construction Company | $21,432,349 | 108 | 4 |
| 96 | Securitas Security Services, USA, Inc. | $21,288,031 | 192 | 2 |
| 97 | State of Ill/ Department Emp SecuriGov | $21,189,077 | 17 | 1 |
| 98 | Metropolitan Water Reclamation of Greater Chicago | $21,084,871 | 75 | 1 |
| 99 | New City Redevelopment, LP | $21,066,667 | 4 | 1 |
| 100 | AT&T Enterprises, LLC | $20,754,888 | 632 | 2 |