Recently, Straight Up Chicago Investor welcomed back Tom Raleigh, founding attorney of Halsted Law Group. The last time Tom appeared on the podcast was Episode 40: Navigating Chicago’s Eviction Process. After four years, he’s back to offer practical tips and solid advice for landlords on Cook County evictions in 2025 and how to stay ahead of issues.

Tom offers advice on the eviction environment in Chicago. He covers typical causes for eviction, notices, and procedures for serving notices, court-ordered payment plans, legal and fair housing considerations, and screening suggestions to avoid the eviction process altogether.

Typical Causes for Evictions in Cook County

When Chicago landlords and property managers need to file for eviction, they typically fall into four main categories. 

1. Non-Paying Tenants

Nonpayment is the most common reason Chicago landlords go to eviction court. Unfortunately, many landlords wait too long to act on nonpaying tenants, even with substantial increases in average rent rates in many Chicago neighborhoods. If a tenant falls behind and doesn’t plan to catch up, the back-rent balance can become quite large. Landlords should factor in roughly six more months of nonpayment before getting the tenants out. The longer they wait, the worse it gets.

Tom’s firm filed approximately 10,000 eviction cases between 2021- 2024. In those cases, landlords waited until tenants were an average of three months behind and were owed around $5,000. With court timelines stretching to six months (see above), back-rent can balloon to $10,000 or $15,000 of lost income.

Hot tip: Don’t wait for a tenant to magically get back on track. Yes, show human decency and willingness to work with them, but have a hard “trigger point,” such as 1.5x the monthly rent. If the monthly rent is $1,000, the landlord might decide that once the balance reaches $1,500, it’s time to serve the appropriate notice. If the tenant has a realistic plan, you can dismiss the notice or revert to a payment arrangement. But waiting until the balance is $5,000 can become catastrophic.

2. Lease Violation For Cause (10-Day Notice)

Other causes of eviction besides failing to pay rent could be more pressing. A just cause eviction must demonstrate a repeated pattern of damaging behavior, unauthorized pets or people, noise complaints, or even criminal activity. Tom said his practice is seeing an increase in these types of cases. 

In Chicago, property managers and landlords can issue a 10-day notice for lease violations like:

• Unauthorized occupants or frequent unauthorized visitors

• Excessive noise or ongoing disturbances, especially in common areas, that impact other tenants

• Bringing in pets against lease restrictions

• Criminal or dangerous behavior (e.g., drug dealing, gang activity)

To be successful, the landlord must identify the activity's date and the actual lease violation. The letter gives the tenant 10 days to rectify the situation. If they don’t address the problem, the landlord can file. 

Hot tip: Maybe you have no real intention of filing for eviction, but you have tenants with unwanted behaviors and want to show them you mean business to make them stop. Some landlords leverage a fine for the issue in their 10-day notice to increase the tenant’s motivation for complying. Then, speaking with the tenant, they offer to waive the fine if they address the offending situation. The landlord has addressed the behavior and avoided the time and costs of a court eviction. 

3. Non-Renewal

Lease non-renewals should be more routine. They generally happen when the landlord wants to do extensive remodeling, sell the unit, or if there isn’t a positive landlord-tenant relationship. 

For Chicago properties and those subject to the Chicago Residential Landlord & Tenant Ordinance (RLTO), a landlord must give:

• 60-Day Notice if the tenant has lived there fewer than three years

• 120-Day Notice if they’ve lived there for three years or more

Landlords must also comply with new laws in 2025, like The Landlord Retaliation Act, when giving notice of non-renewals. The law prevents landlords from refusing to renew leases because the tenant exercised their legal rights. Those rights include filing complaints, joining tenant unions, or engaging in other legal actions to improve living conditions. The Landlord Retaliation Act addresses the power imbalance between landlords and tenants by ensuring tenants can assert their rights without fear of retaliation.  

Hot tip: Both notices terminate a lease on the last day of the expiration month. You may be forced to wait an additional month if you miss the exact timeline by even a few days. So, if you file a 60-day notice on January 5, it won’t expire until March 31. That’s because even though 60 days would be March 5, tenants have until the last day of the month before termination of the lease. 

4. Squatter Notice

If you own Chicago investment property (and in many other parts of the nation), squatters have become a serious problem. There are many different flavors of squatters. Most often, squatters are just people who stealthily move on into vacant properties without consulting anyone. It gets a little trickier with another flavor of squatter who claims they thought they had a valid lease but have been scammed by someone else. 

Because squatters use the internet as much as the rest of us, they share tips and trade secrets and get craftier. As the process stands now, owners must submit a Demand for Immediate Possession (aka “Squatter Notice”) to have squatters legally removed. Meanwhile, squatters can cause untold damage while the owner goes through the process. Tom hopes that future legislation may simplify the process.

Recently, George McCleary was on SUCI to talk about squatters and the even wilder new trend of creating fake title deeds on properties and “selling” them away from the rightful owners. He also shared some of the more interesting ways owners flush out squatters. We also know of another owner who took a more extreme route to smoke out squatters in his property.

[Embed video: Combat Squatters and Title Deed Fraud] 

George McCleary had his “I Stole a House” video go viral. In it, he impersonated a squatter and explained how they do it. As a result, he’s heard squatter horror stories from around the world. Recognizing the need to address this massive, global problem, George created the Squatter Defender Training Course to help educate owners on their options for dealing with squatters in their properties.

Hot tip: Don’t assume your rental property’s location keeps it safe from squatters. Squatters are a problem everywhere. Red states. Blue states. Big cities. Small towns. Rural areas. It’s a veritable Dr. Seuss book of places squatters target. If you can’t drive by and visit a vacant property regularly (daily is best), technology can serve as your eyes and ears. A few cameras and a talk-back system help you identify if anyone is in your house who shouldn’t be and let them know you see them.

The Changing Eviction Landscape in Chicago

Over the past few years, evicting tenants has become increasingly more complex, taking longer from filing to move out. 

The 60-Day Process that Takes Six Months

Every month a landlord doesn’t receive rent cuts into profits. Delays in rent money can get them into financial hot water personally if they need to cover the mortgage or other expenses. 

Pre-COVID, the typical process to evict a tenant in Cook County would take around two months. Some landlords might have a shorter timeline if the tenant clearly defaulted and had no defense. 

Since then, Cook County has increasingly become tenant-friendly. The process now offers even more chances in a more complicated process for tenants to get their rent current. As a result, Chicago landlords can expect a lengthy legal process that can last up to six months (or more). Worse, one error in any step can result in a timeline reset.

So what’s changed?

• Court Procedures
  Many eviction hearings in Cook County are now conducted via Zoom and funneled through an Early Resolution Program (ERP). The ERP has good intentions, allowing Cook County tenants to access resources like rental assistance, a mediator, or other ways to repay balances in full. However, Tom said that 95% of the time, tenants in the cases he’s filed only use the ERP as a delay tactic.

• Inconsistent Court Schedules
  Everything from scheduling issues to remote hearing chaos can slow the wheels of justice. Some judges only sit on eviction matters on certain days of the week, or large dockets are rescheduled for various reasons. Sadly, despite conducting most appearances virtually, this has not necessarily resulted in streamlined efficiency.

• Tenant Leverage
  Tenants know eviction takes a long time. Many stay put, recognizing that the legal system's disarray can buy them time. Sly tenants might also file last-minute motions to vacate a default order if they fail to appear on their scheduled court date. This could add even more weeks of waiting for a new hearing.

These changes mean Cook County landlords need to know how to protect themselves. That starts with a better understanding of the basic reasons you’d file an eviction and the procedures to follow for each one.

Court-Ordered Payment Plans

Given the six-month timeline for a contested eviction, Tom’s practice encourages landlords to work out structured payment plans with tenants that are enforceable through court.

Sound counterintuitive? Why can’t you create your own payment plan and have a tenant sign an agreement saying they’ll catch up with an extra $500 monthly? Well, any random piece of paper holds little weight in court. If a tenant defaults, you must start the eviction process from scratch.

Instead, many Chicago attorneys propose an “Agreed Order” at the first eviction hearing. The steps look like this:

1. File the eviction case (at least you’re in line, timewise, if it fails).

2. Discuss settlement at your first court date, often via Zoom or phone.

3. Draft an agreed order where the tenant commits to paying the current rent plus a set monthly amount toward arrears. The tenant waives the right to trial or jury (so if they default, the landlord can more quickly get an eviction order).

4. If the tenant makes their monthly and arrears payments on time, the landlord agrees to dismiss the case at the end of the agreed period.

5. If the tenant fails, the landlord’s attorney informs the judge of the missed payment under the agreed order. 

6. The judge issues the eviction order without another multi-month delay.

From the tenant’s perspective, it’s a good outcome if they want to remain in the property and can realistically afford a catch-up schedule. They can show good faith by making a partial payment immediately and avoid having an eviction on their rental history. 

This works for landlords because it keeps a paying tenant in place, assuming they can cure the default. It often prevents them from re-filing if things go wrong because the tenant already agreed to the settlement before the judge. Meanwhile, the landlord doesn’t sit on a mounting balance while time drags on.

One Important Note: If you set a payment plan, you might have a status hearing to see if the tenant made a scheduled “good-faith” payment. If so, the judge may require you to track future compliance. If the tenant fails at any subsequent point, you must promptly file the paperwork to enforce the eviction order. Many landlords forget to do so right away, losing valuable time.

Decrease in Rental Assistance Program Acceptance

By law, an eviction case is dismissed when a tenant is approved for rental assistance. However, it’s becoming increasingly difficult for tenants to receive approval… and the decision is taking longer. 

For example, in 2024, Tom’s practice saw 3,000 cases where tenants applied for rental assistance. Of those, only 300 were approved. Plus, those approved accrued even higher back rent with those longer delays. 

So, if a tenant applies for $10,000 in assistance and is approved (assuming they’re among the lucky ones), they owe $13,000. Where does that other $3,000 go? Landlords have started accepting that $10,000 payment and then serving a fresh five-day notice to get back into court and restart the process for the balance. 

It’s also evident that the rental assistance program is having processing issues. Tom said it’s common for tenants and landlords to file paperwork in the rental assistance portal and then receive email notifications that they’re missing documentation even if they’ve already submitted it. Landlords and tenants often submit the same paperwork four or five times. Heaven help you if you miss an email… you’ll be looking at longer delays. This is frustrating, expensive, and wastes unnecessary time and energy.

Some landlords (like Tom himself) will apply for rental assistance with their tenants on the condition that the tenants sign an agreed order. In the order, the tenant acknowledges they’re in arrears a certain amount but agrees to pay rent moving forward while waiting for a decision. If approved, the owner receives the back pay and the $500 filing fee, and everyone moves on. If they’re declined, with the order, the tenant must pay their monthly rent plus an additional amount (say $500) toward the back rent. The landlord spreads the repayment over a longer timeline to make it manageable for the tenant. This protects the owner and tenant.

Updates to Notices and Procedures

Many changes in procedure in the last few years have complicated how landlords can submit notices. Staying on top of changes is imperative for landlords to comply with local, state, and federal laws. 

Five-Day Notice Becomes a 30-Day Notice Under The CARES Act

For years, the landlord’s standard tool in a nonpayment situation has been a five-day notice (as in rent is five days late). If the tenant paid within that timeframe, they couldn’t proceed to court. The landlord had grounds to file the eviction if they failed to pay. However, a major complicating factor emerged during (and after) the pandemic: the Coronavirus Aid, Relief, and Economic Security (CARES) Act.

A lesser-known portion of the CARES Act states that landlords must serve a 30-day notice instead of five if they hold certain federally backed mortgages (e.g., Fannie Mae or Freddie Mac) or the tenant receives federal housing subsidies (e.g., Section 8). 

Many Chicago landlords inadvertently find themselves subject to this requirement because they have a loan indirectly owned by Fannie Mae or Freddie Mac, or their tenant has a Housing Choice Voucher.

A difference of 30 days instead of five can drastically shift timelines and be a rude surprise to a landlord expecting an otherwise expedited process. 

Parts of the CARES Act sunsetted as the pandemic ended. But the eviction-related provisions may be here to stay. So, landlords should continue to monitor whether their property or tenant may trigger these extended notice requirements. 

Hot Tip: If you’re unsure about the type of notice to serve, consult with an attorney or an experienced property manager. Mistakes in notice and service can lead to your case being thrown out (and you’re back at square one with the timeline reset).

Source of Income and Voucher Holders

In Chicago and throughout Cook County, it’s illegal to discriminate based on the source of income, including Housing Choice Vouchers (e.g., Section 8). You’re not required to lower your rent or overlook legitimate screening concerns, but housing providers cannot refuse to rent to applicants with housing subsidies.

The Illinois Human Rights Act, a portion of the Illinois Fair Housing Laws, requires housing providers to treat all applicants and tenants equally regardless of their source of income. Source of income can mean Section 8 rent, social security, and other subsidies willing to pay a tenant's portion of rent monies to the landlord.

Let’s say a voucher covers $1,000 of the rent, but the tenant is responsible for the other $300. You can only evaluate that $300 portion for nonpayment or shortfall. If the housing authority fails to pay its portion, you cannot hold the tenant responsible.

Legal and Fair Housing Considerations

An increasingly common scenario is that a landlord denies an applicant with a housing voucher or a lower credit score. Not long afterward, the landlord receives a letter from a local fair housing or tenant advocacy group accusing them of discrimination. The landlord might panic, worry about lawsuits and legal fees, or bury their head in the sand—none help. 

Here’s a better approach:

1. Stay Calm and Gather Info: Collect written screening criteria, the application, the credit/background report, and any notes.

2. Seek Legal Advice: An attorney experienced in fair housing can help you craft a polite but professional response.

3. Communicate: Nonprofits often submit letters to determine whether you provided a fair and non-discriminatory screening. Be transparent. Explain your denial's legitimate reasons, such as insufficient income or major recent delinquencies. Then, point to your consistent, documented screening policies. 

4. Consider an “Individualized Assessment”: Sometimes, you might invite an applicant to submit more documentation or add a co-signer. If you remain steadfast in your denial, your best defense is using the same objective criteria for them as for every other applicant.

No More Sheriff Service Requirement

On a more positive note, a 2025 law removed the requirement to pay the Cook County Sheriff to serve eviction notices to tenants. 

For years, landlords and property managers in Chicago and the surrounding areas had to rely on the sheriff's office to carry out eviction orders, often with low success rates. The bottleneck frequently created backlog delays, lengthy wait times, and inefficiencies.

Instead, private process servers can now handle eviction-related tasks, streamlining and drastically improving the entire process. Plus, with the flexibility to choose preferred private servers, owners and their attorneys can select those with the best possible outcomes.

Avoiding Evictions in the First Place

Because the eviction process is long, arduous, and expensive, landlords should do everything possible to avoid them. The best eviction is the one you never need to file! It is possible to have a large rental property portfolio and zero eviction filings. 

An effective tenant screening program balances compliance with local ordinances and fair housing laws against the landlord’s need for financially stable residents.

Evolving Beyond Simple Credit Scores

Historically, many landlords routinely denied anyone with a credit score under 650 or prior evictions. No exception. 

However, that approach can inadvertently block out many otherwise qualified renters, especially in workforce or affordable housing segments. Meanwhile, landlords might still rent to a 700-credit-score tenant on the verge of losing their job.

Willingness to Pay

Some screening services or third-party platforms, like Tom’s Rent Butter, now offer more nuanced data, examining both credit scores and the applicant’s financial behavior over time. 

Rather than focusing on years-old defaults or raw debt load, these services detect patterns: Do they apply for numerous payday loans every month? Do they pay their utilities and phone bills on time? Have they built discipline, suggesting they’ll meet their rent obligations moving forward?

Although two applicants might have a 580 credit score, one has turned over a new leaf, consistently paying major bills on time for 12 consecutive months. Meanwhile, the other has a recent spree of missed payments or new collections. The first applicant could be the perfect candidate despite the slightly higher risk profile. 

Consistency with Fair Housing Laws

Landlords should apply uniform criteria to all applicants to avoid discrimination. But a rigid, one-size-fits-all approach might unintentionally sideline entire classes of people, especially in specific neighborhoods.

To remain consistent with Fair Housing Laws:

• Have written criteria for things like income-to-rent ratio, prior rental history, and criminal background guidelines

• Allow for individualized assessment if an applicant appears borderline but shows mitigating factors such as a stable job or only older credit blemishes

• Document decisions so you can explain them later if challenged by a housing advocate

DOWNLOAD EBOOK: MASTERING TENANT SCREENING IN 2025

1. Start the Clock Early

If the rent is overdue and you suspect the tenant is experiencing a genuine hardship they cannot overcome, serve notice sooner rather than later. You can always back down if the tenant pays. But if you wait three or four months, the court process alone can consume another half-year, leaving you with a huge financial hole.

2. Cash for Keys

Sometimes, paying a problematic tenant to leave the unit early is cheaper and more humane. If you calculate that a contested eviction might cost you $3,000 in attorney fees and months of unpaid rent, offering that same $3,000 to the tenant might get them out in under a month. Draft a written agreement that states they must hand over the keys, surrender possession, and remove all personal property. Just do things properly to avoid expensive mistakes.

3. Track Rental Assistance Carefully

Various rental assistance programs can be a lifeline for tenants. However, many landlords have found these approvals can drag on, with repeated requests for the same documents. Respond promptly to requests and know that accepting partial payment (like a large chunk from a rental assistance program) might obligate you to dismiss the current eviction.

4. Explore Court-Ordered Agreements

Where feasible, use agreed orders to avoid the repeated “start from scratch” scenario if the tenant defaults repeatedly. It also demonstrates a good-faith effort to keep a paying tenant in place, which can look favorable if the matter later escalates in front of a judge or a fair housing claim.

5. Validate Your Notices

Be clear about which notice—five-day, 10-day, 30-day, 60-day, 120-day— applies to your current situation. Double-check the deadline for when that notice must expire, or risk re-serving and losing valuable time.

6. Document, Document, Document

Anytime you communicate with a tenant, keep a short written record. If you get dragged into an eviction or fair housing dispute, your detailed notes can be the difference between a swift resolution and a messy legal entanglement. Conduct pre-move-in inspections and keep all photos and videos, which can later prove damage if the tenant disputes any claims at move-out.

7. Lean on Professional Resources

Managing the day-to-day intricacies of property management, especially if you own multiple units or live far away, is nearly impossible. Consider hiring a professional property manager to help streamline rent collection, screening, and lease enforcement while saving you money in the long run.

Contact us today to learn how our expert property management team can help you navigate or avoid the eviction process altogether.