A lawsuit filed Tuesday, July 28, in Cook County Circuit Court could force delayed property tax bills into the mailboxes of North Shore commercial property owners along Green Bay Road, Elm Street in Winnetka, and Central Street in Wilmette weeks sooner than expected.

The Illinois Federation of Teachers sued Cook County Treasurer Maria Pappas, seeking a court order to immediately mail second-installment property tax bills and compensate taxing districts for revenue lost during months of delays. IFT attorney Stephen Yokich filed the suit on behalf of roughly 50,000 union members countywide, including suburban teachers in North Shore school districts.

"State law has specific deadlines in it for sending the bills and distributing the money, and the state law doesn't really give the treasurer any discretion with respect to distributing the money," Yokich told the Chicago Tribune.

What it means for North Shore businesses

The billing delay hits North Shore commercial property owners especially hard. New Trier Township underwent a Cook County Assessor reassessment in 2025 that raised total assessed values 39%, according to the Assessor's office. That reassessment covers Glencoe, Winnetka, Wilmette, Kenilworth, and portions of Glenview and Northfield. The higher assessments will land on the same second-installment bills that are now months late.

For landlords and tenants negotiating leases along Park Avenue in Glencoe, Waukegan Road in Northfield, or the Wilmette business district near the Metra station, the delay means they cannot see final tax numbers before making financial decisions. In a typical year, those bills arrive by July 1 with an Aug. 1 due date. The county's June 2026 announcement estimated bills would arrive around Oct. 1, though the Tribune reported some county officials have expressed optimism they could land by Sept. 1.

$400 million held back, $300 million in bridge loans

The Treasurer's office has held back about $400 million from the last tax cycle because it and contractor Tyler Technologies still need to reconcile over- and underpayments to taxing districts, according to the Tribune. The technology upgrade that caused the cascading delays has cost $63 million to date, more than double the original $30 million contract approved in 2015.

North Shore taxing districts, including school districts, park districts, and library districts in all five communities, can apply for no-interest bridge loans through Cook County's $300 million Property Tax Bridge Fund. The application window opened Monday, July 20, and closes Monday, Aug. 24, according to the county. Whether any North Shore district has applied has not been confirmed.

Chicago Public Schools estimates it spent $40 million in interest because it had to borrow during the delay, a figure that illustrates the cost to taxing bodies across the county.

What happens next

No hearing date for the lawsuit has been set. The Treasurer's office said Tuesday, July 28, it intends to post tax bills online once it receives the billing file from the Cook County Clerk's office and verifies the numbers. Clerk Monica Gordon's office must finish calculating tax rates before Pappas can act.

North Shore property owners waiting for bills should monitor the Cook County Treasurer's website for posting dates. Residents who believe their 2025 reassessment was inaccurate can still file appeals through the Cook County Assessor's office.