Photo by Roman Novitsky

By Don DeBat

November 26, 2025 – Are you one of the 1.8 million Chicago and Cook County property owners who is wondering why the second installment of the 2024 real estate tax bill wasn’t mailed until November 14 instead of the usual August 1?

This year’s delay centered on the decade-long and expensive upgrade to the internal systems used across the county’s property tax offices – including offices of the Assessor, Treasurer, and Clerk – overseen by the county’s “Bureau of Technology” and carried out by Texas-based Tyler Technologies.

Homeowners finally will now be able to include those tax payments on their annual income tax filings, while ensuring taxing bodies will see much-needed revenue before the end of the year – though they might be less stoked to make massive payments to the county coffers right before the holidays.

Now, this will be the first billing cycle fully conducted under the new “Tyler System,” and off the county’s previous, decades-old mainframe.

Though officials had hoped to wrap up the upgrade by Memorial Day 2025, a multitude of problems cropped up while calculating the final property tax bills, leaving some owners incorrectly on the hook for hundreds or thousands more than they should have paid.

Bill calculations involve dozens of inputs across the three key offices:

• Assessor Fritz Kaegi’s office shares final estimates of value for each property.

• Clerk Monica Gordon’s staff calculates annual tax rates based on each local levy. Bills must also include exemptions and incentives before the treasurer posts and mails them.

• Then funds must be distributed back to each of those villages, libraries, and school districts.

The Tyler upgrade affected all of those offices but was partly refereed by the Bureau of Technology under Cook County Board President Toni Preckwinkle (right).

Internal fixes involved several rounds of testing and recalculation between Tyler, the Treasurer, and often the Clerk. County officials complained that often when one issue was fixed, another cropped up. Staff had been working repeated weekend shifts to continue testing and correcting issues.

Despite early complaints about staffing shortages, Tyler officials said they were committed to the project and countered that officials had not sufficiently prepared to switch off the old system. Kaegi’s efficient Assessor’s Office largely completed their portion of the Tyler upgrade in 2021.

Cook County Treasurer Maria Pappas (left), a Tyler critic, who at times urged the county to fire the firm or file suit for their shortcomings, threatened to not send out bills if they were even a penny off.

County commissioners, echoing complaints from their residents about the late bills, feared that the tight turnaround between these late bills and the next installment – due in the spring – would be a major stressor for some taxpayers.

Taxing bodies with low cash flow were also starved of a revenue source that typically comes through before the start of fall. Preckwinkle, with the approval of the county board, launched $300 million in “bridge loans” to float those municipalities until tax revenues began flowing again.

Certificates of error, which are refunds issued for missing exemptions, had been on hold during the Tyler problems for several months, as were refunds for overpayments or duplicate payments on past bills.

Officials will now begin processing that backlog.

Preckwinkle and Pappas also supported legislation that passed in Springfield that would delay the next due date by one month, giving taxpayers a bit more breathing room between major bills.