| St. Linus Parish Catholic Bishop of Chicago | Other Services (except Public Administration) | $350,770 | $353,788 | 47 | N/A | AI Deep Dive |
| St. Catherine of Alexandria | Other Services (except Public Administration) | $347,228 | $349,581 | 72 | N/A | AI Deep Dive |
| Crown Mortgage Company | Finance and Insurance | $332,877 | $0 | 23 | $11.8M | AI Deep Dive |
| Francesca's Oak Lawn LLC | Accommodation and Food Services | $321,366 | $324,490 | 40 | $7.1M | AI Deep Dive |
| Women Health Institute, Ltd. | Health Care and Social Assistance | $312,530 | $253,374 | 15 | <$5M | AI Deep Dive |
| Home Healthcare Solutions Co LLC | Health Care and Social Assistance | $308,773 | $310,720 | 20 | <$5M | AI Deep Dive |
| Regency Home Health Care PC | Health Care and Social Assistance | $304,957 | $306,709 | 67 | $15.5M | AI Deep Dive |
| Drs. Leahy & Disalvo-Ost PC | Health Care and Social Assistance | $302,703 | $304,367 | 19 | <$5M | AI Deep Dive |
| American Express Trading, Inc. | Wholesale Trade | $300,000 | $303,592 | 10 | <$5M | AI Deep Dive |
| Jmam Inc. | Accommodation and Food Services | $297,002 | $298,595 | 35 | $6.2M | AI Deep Dive |
| Ac Fox INC | Accommodation and Food Services | $296,245 | $298,483 | 20 | <$5M | AI Deep Dive |
| St. Germaine Parish | Other Services (except Public Administration) | $294,238 | $296,068 | 44 | N/A | AI Deep Dive |
| Regency Home Health Care PC | Health Care and Social Assistance | $294,027 | $296,756 | 420 | $71.9M | AI Deep Dive |
| United Rehab Providers, Inc. | Health Care and Social Assistance | $288,297 | $290,910 | 500 | $135.0M | AI Deep Dive |
| Kenwood Liquors INC | Retail Trade | $287,335 | $289,129 | 38 | $5.8M | AI Deep Dive |
| Associates in Rehabilitation Medicine, S.c. | Health Care and Social Assistance | $279,277 | $281,907 | 15 | <$5M | AI Deep Dive |
| Carden Group INC | Construction | $275,284 | $278,014 | 16 | <$5M | AI Deep Dive |
| Drs. Leahy & Disalvo-Ost PC | Health Care and Social Assistance | $273,813 | $304,191 | 19 | <$5M | AI Deep Dive |
| Petty & Bielik Orthodontics, P.c. | Professional, Scientific, and Technical Services | $273,137 | $276,674 | 25 | <$5M | AI Deep Dive |
| Coach Eve Learn to Swim, LLC | Educational Services | $262,573 | $211,078 | 7 | <$5M | AI Deep Dive |
| Coach Eve Learn to Swim, LLC | Educational Services | $262,572 | $265,286 | 9 | <$5M | AI Deep Dive |
| Horizon Pharmaceuticals INC | Manufacturing | $260,116 | $264,456 | 19 | $18.8M | AI Deep Dive |
| Associates in Rehabilitation Medicine S.c. | Health Care and Social Assistance | $258,898 | $261,976 | 14 | <$5M | AI Deep Dive |
| Hiotis Enterprises, Inc. | Retail Trade | $254,000 | $257,358 | 90 | $22.7M | AI Deep Dive |
| Women Health Institute, Ltd. | Health Care and Social Assistance | $251,280 | $252,984 | 21 | $6.6M | AI Deep Dive |