It has been a hard year for Chicago as a whole, with many issues coming to the surface. While many are beyond the Windy City’s control, a rather large one was self-inflicted. Already saddled with the second-highest property taxes in the nation, Cook County complicated matters by completely botching the rollout of the current property tax bills. While it had been a problem in the past, notably in 2021, a large computer snafu completely derailed the plans of the Cook County Assessor’s Office (CCAO), the County Treasurer, the County Clerk, and the Board of Review (BOR) earlier this year. This meant that the second installment of Cook County property taxes was delayed indefinitely.
In essence, the computer errors caused a spiral of delays and mistakes across the county. Why this happened and who is to blame was never truly found out. Instead, every party blamed the other. As usual, this leaves taxpayers holding the bag. Initially planned for a July release and an August payment deadline, Cook County tax bills should finally hit mailboxes in the next few days. Needless to say, millions of taxpayers getting handed huge bills in the middle of the holiday season is a disaster all around.
Second Installment to be Mailed on November 14
While no tax bill is eagerly awaited, the anticipation over the second tax bills in 2025 has had people across the county on the edge of their seats for months. With rising values and huge totals, over 1.8 million taxpayers have been expecting the worst. These bills will finally be mailed out on Friday, November 14, 2025. This means that the people of Chicagoland will be getting a nasty surprise in their mailbox just in time for Thanksgiving. And this is only adding to a bill that is notorious for being unpredictable.
Unlike the first installment, the second tax bill uses exemptions, tax rates, and the equalization factor from 2025, rather than 2024. This means that many taxpayers are going in blind. As tax rates and the equalization factor both have huge impacts on the size of bills, this can mean that taxpayers are going to be hit by a bill that is not only late but also much higher than expected. This could mean that the money put aside for months might not be enough to cover the new levies.
Property Taxes are Due December 15
Being mailed out in mid-November means that taxes are likewise due in mid-December. While the mailings crash Thanksgiving, the due dates will be there to haunt the December holidays. December 15, 2025, is the hard deadline for due taxes. If payments are even a day late, penalties and interest will begin occurring. This can quickly lead to a spiral of snowballing costs that must be addressed as soon as possible. This makes it imperative to pay taxes as soon as possible.
Due Date for the First Installment of 2026 Pushed Back to April
If you are worried about the second installment in 2025 and the first installment of 2026 being back-to-back, you will at least find some relief to start the new year. The first installment of tax bills is typically due in March, with bills being mailed in February. The CCAO and other bodies responsible for taxation have correctly decided that this will be too much of a burden for the average person in Cook County. Instead, the county plans to send out bills in March of 2026, with them coming due in April. While not the largest of delays, it will hopefully give enough of a buffer for the harried people of Cook County to get everything settled.
The 2025 Delays Prove why Appeals are Vital
Taxes have increased in Cook County for over 30 consecutive years, and this seems to show no signs of slowing down. It has recently been announced that massive tax breaks could be handed out to “Megaprojects” in the future thanks to House Bill 4058. This would give incentives and delayed taxation to large commercial projects. While these are supposed to create jobs, they could lead to small businesses and homeowners footing the lion’s share of taxation instead. It has previously been revealed that large businesses were benefiting from appeals, while those costs were transferred to homeowners, especially low-income, minorities, and the working-class. To top things off, all legislative attempts to create reasonable taxation have failed.
The only way to protect your property is to use appeals to challenge your taxable value. Even the CCAO has championed that every property owner should protest their taxes, as they cannot guarantee that their own assessments are correct. Protests cannot change the current tax bill, but they can lower assessments in the future, hopefully keeping taxes to a reasonable level. Many homeowners have saved their houses thanks to using this option, and the BOR is seeing record appeals every year. The best way to approach appeals is to do so every year, so that you are protected against price spikes and the dreaded triennial reassessment.
O’Connor Can Help
The delayed tax bills, countless errors, and possible corruption seen in Cook County should encourage you to challenge your taxable value. We at O’Connor are here to support you. While we cannot appeal your taxes for you, we can do careful analysis of your valuation, property equity, gather evidence, review your assessment, and use our proprietary database to compare property sales. We can then use this evidence to coordinate with attorneys that know the best ways to appeal and how best to meet the requirements of the CCAO and the BOR. With our evidence in-hand, you and your legal team will be set to protect your property now and in the future. We will review your taxes every year and coordinate appeals if necessary. You will not be charged for these analytic and data services unless your taxes are lowered.
