The Ever-Present Computer Issue

We have covered it in many articles, but the main cause for all of these collective issues is a series of computer issues in Cook County government. Originally conceived as a way to unite the Cook County Assessor’s Office, Treasurer, and County Clerk into one system for property taxes, constant problems have led to numerous delays. While 2025 was certainly not the start, it was by far the most severely affected year. Both installments of Cook County property taxes were delayed, which pushed deadlines back months. The second installment of property taxes was eventually mailed in November with a due date in December. Coming late and in the middle of the holidays proved to be very poor timing for millions of taxpayers, which was further complicated further by a 16% increase in homeowner’s property taxes.

2026 Delays

Thanks to the late bills to end 2025, the first installment of bills in 2026 was intentionally delayed by one month to give breathing room to taxpayers across Chicagoland. It was then intended for Cook County to be back on its traditional schedule, with bills going out in July and due dates falling in August. However, it seems that the ripple effects are still being felt, and the Cook County Treasurer announced that bills would be delayed an additional two months, with a mailing deadline set for September. Although more delays were initially feared, it appears that this schedule is holding. However, this does leave a gap in funding for schools, as revenue will not start coming in until after school has been in session for several weeks.

A Funding Deficit to Start the Year

School districts across Cook County were already reeling from the 2025 delays, which cost the Chicago Public Schools (CPS) system $34 million in interest and other costs alone. While funds are used to cover operating costs and pay for staff and faculty, they are also used to cover the ballooning pension costs, which are also a growing issue. Paying for this short-term funding only puts school districts in a bigger hole, which makes it imperative to begin the next round of funding as soon as possible.

Uncertain Budgets

With funding up in the air, many school districts have had a tough time creating a firm budget. Since a budget needs to be in place to get short-term loans, this puts many school districts in a bind. For instance, the CPS was able to pass a budget at the end of July, but it contained several caveats that were not confirmed when it was voted on. This includes a $150 million in funding from the state of Illinois, which has yet to be approved. While the school year should start off fine, the district might not be able to cover payroll as soon as September. Districts outside of Chicago, such as Evanston, also need to obtain bridge loans to stabilize their budgets, which can then be used to secure other loans for short-term financing. These are tax anticipation warrants and have become incredibly common in Cook County over the past five years.

Furloughs and Layoffs

Delayed budgets and payrolls create the possibility of faculty and staff losing their jobs or at least going without paychecks. Several school districts have chosen to lay off teachers in order to make tight budgets. Others will ask teachers to either take furloughed or unpaid ones in order to keep things functioning until funding can be restored. Many school districts hope to use loans to bridge the gap in an effort to keep their roster intact. Many school districts, including CPS, are doing their best to avoid layoffs in their budget, but keeping these jobs is dependent on state funding or loans.

Will Cook County Schools Start on Time?

The biggest question that many parents have is whether schools across the Chicago area will be ready to open when the school year starts in a few weeks. It is currently believed that school districts will be able to open on time thanks to loans or state action. However, these loans can have large interest rates, which can haunt districts in the future. The next few weeks will be incredibly important, as school districts across Cook County will see if they can secure funding in time for kids to start their school year. Even if funding does not come through, school districts may try to manage operations until revenue streams can be secured.

Chicago Teachers Union Sues to Have Tax Bills Sent Earlier

During the Chicago Bears saga, the Chicago Teachers Union (CTU) opposed the “Megaprojects” bill, as they believed it would have damaged education in the long term thanks to massive cuts for large corporations. They have stepped into the arena again by filing a lawsuit against the Cook County Treasurer. The goal is to force the Cook County Treasurer to send the second installment of tax bills as soon as possible, bypassing the delay. This demonstrates how dire the situation is getting in Cook County. However, even if the suit is successful, it is believed that it will have little consequence, as a court order cannot make things move any faster. It is still indicative of how things are going and what school districts, taxpayers, and parents can expect in the future.

Continuing Tax Uncertainty

“Tax uncertainty” became a buzzword during the Chicago Bears debate, as the iconic franchise said that this was the primary reason for their pondered move to Indiana. The randomness of tax bills and the amounts attached to them have become commonplace, and not just in the last five years due to computer errors. Both businesses and homeowners are experiencing an unstable property tax system, which can result in sudden spikes, such as those observed at the end of 2025. This can be made worse by the triennial reassessment, during which the CCAO reassess one- third of the county under a magnifying glass. Taxpayers in Cook County have learned that they must take matters into their own hands, with a record number turning to property tax appeals to tip the scales in their favor.

Property Tax Appeals Opening Across Cook County

Property tax appeals enable taxpayers to challenge the taxable values placed by the CCAO, which can result in strong property tax reductions. They also have the added benefit of fixing errors and establishing the true value of a home or business, which helps prevent future spikes during reassessment. The use of appeals is backed by the CCAO, the Cook County Treasurer, and many other government entities. Once a notice of assessment is mailed, Cook County taxpayers have 30 business days to file an assessor appeal with the CCAO. Later in the year, if they miss the deadline or do not get a settlement, they can file another appeal with the Board of Review (BOR). Some townships have already closed their assessor appeal windows, while others are starting to open. With so much up in the air, every taxpayer should be exploring their options.

O’Connor Provides Expert Evidence for Appeals

For an appeal to be successful, there must be both strong grounds and evidence to back it up. For instances of overassessment, when a property is assessed at a value higher than its likely sale price, this means sales records dating back three years. For instances of unequal assessment, this means collecting assessments. In either case, these comparable properties must have similar characteristics to your property, including having similar sizes, locations, and ages. Getting the best evidence possible is usually the biggest hurdle facing any taxpayer.

We at O’Connor are here to take care of this major obstacle, as we provide premium evidence and analysis for appeals. First, we will go over your assessment to spot any issues. Next, we will use data-driven analysis and proprietary databases to find the relevant comparable properties to help prove what your home or business is truly worth. Finally, we will coordinate an appeal with a law firm that has decades of property tax experience. You will not pay for this analysis or evidence unless your property taxes are lowered.