| Heads Up Logistic Services LLC | Professional, Scientific, and Technical Services | $27,145 | $27,391 | 2 | <$5M | AI Deep Dive |
| Winnetka-Northfield Chamber of Commerce | Other Services (except Public Administration) | $27,125 | $27,243 | 5 | <$5M | AI Deep Dive |
| Conneys Elm Street Pharmacy INC | Retail Trade | $27,082 | $27,389 | 2 | <$5M | AI Deep Dive |
| Sarac Pest Control Inc. | Administrative and Support and Waste Management | $27,012 | $27,263 | 11 | <$5M | AI Deep Dive |
| Van Ake Capital LLC | Finance and Insurance | $26,750 | $26,983 | 1 | <$5M | AI Deep Dive |
| Madison Corporate Group, Inc. | Real Estate and Rental and Leasing | $26,300 | $26,482 | 2 | <$5M | AI Deep Dive |
| Papergirl Pr & Marketing INC | Professional, Scientific, and Technical Services | $26,065 | $26,197 | 3 | <$5M | AI Deep Dive |
| Cafe Aroma LLC | Accommodation and Food Services | $25,270 | $25,588 | 7 | <$5M | AI Deep Dive |
| Traverse Consulting INC | Professional, Scientific, and Technical Services | $25,000 | $25,191 | 1 | <$5M | AI Deep Dive |
| Traverse Consulting INC | Professional, Scientific, and Technical Services | $25,000 | $25,144 | 1 | <$5M | AI Deep Dive |
| Physicians Medspa Partners LLC | Health Care and Social Assistance | $25,000 | $25,265 | 3 | <$5M | AI Deep Dive |
| Junior League of Evanston-North Shore | Health Care and Social Assistance | $24,330 | $24,546 | 7 | N/A | AI Deep Dive |
| S.a.u.r. Inc. | Retail Trade | $24,190 | $24,265 | 10 | <$5M | AI Deep Dive |
| Skp1 INC | Unknown | $23,600 | $0 | 1 | N/A | AI Deep Dive |
| Twisted Twins INC | Administrative and Support and Waste Management | $23,426 | $23,733 | 1 | <$5M | AI Deep Dive |
| Adelheidi's of Winnetka, LLC | Retail Trade | $23,200 | $23,414 | 4 | <$5M | AI Deep Dive |
| Theresa Cullen | Retail Trade | $23,075 | $23,393 | 6 | <$5M | AI Deep Dive |
| Tj Cullen Jeweler | Retail Trade | $23,075 | $23,340 | 6 | <$5M | AI Deep Dive |
| Linda Martin DBA Linda K Martin | Real Estate and Rental and Leasing | $22,910 | $23,246 | 1 | <$5M | AI Deep Dive |
| Ardeshir Raghian DDS PC | Health Care and Social Assistance | $22,872 | $23,027 | 2 | <$5M | AI Deep Dive |
| Artists Concepts LLC | Professional, Scientific, and Technical Services | $22,860 | $21,038 | 1 | <$5M | AI Deep Dive |
| Sayen El | Wholesale Trade | $22,800 | $23,056 | 1 | <$5M | AI Deep Dive |
| Massage Therapy Center of Winnetka, Inc. | Other Services (except Public Administration) | $22,500 | $22,619 | 2 | <$5M | AI Deep Dive |
| Susanne Simmons | Health Care and Social Assistance | $22,500 | $22,701 | 1 | <$5M | AI Deep Dive |
| Home Ice Hockey, LLC | Retail Trade | $22,400 | $14,158 | 4 | <$5M | AI Deep Dive |