I hope you have some takeaways from this blog. if you want our team to provide you tenant placement or property management. Click Here
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

Let’s be real for a moment—no one invests in Chicago real estate with dreams of sitting through eviction court. Whether you’ve got a vintage two-flat in Humboldt Park or a six-unit walk-up in Pilsen, every landlord has one thing in common: the desire to collect rent without drama. But even in 2025, with all the tech, automation, and tools at our fingertips, we’re still seeing landlords caught off guard by the same preventable scenarios. It’s not the market—it’s the process.

And here's the hard truth: the vast majority of evictions in Cook County happen not because the tenants are inherently bad people, but because the landlords never put the right screening and enforcement policies in place.

This isn’t about being a tough guy. It’s about consistency, documentation, and understanding the law. The goal isn’t confrontation—it’s prevention. And if you follow the steps I’m about to outline, you won’t just reduce your evictions—you’ll eliminate them altogether.

I know that’s a bold claim. But after managing over 6,000 units, leasing 5,000+ apartments, and clearing over 60,000 work orders at GC Realty, I’ve seen firsthand what works and what gets you dragged into court.

Let’s walk through exactly how to set up your tenant screening and rent enforcement policies to get to that elusive number: zero evictions.

It All Starts With Consistency—Not Aggression

Too often, landlords fall into two extremes: they either wait six months to act while rent stacks up, or they drop a five-day notice that the second rent is one day late. Neither approach works. The secret sauce? Serve your five-day notice the day after your lease’s grace period ends.

If your lease says rent is due on the 1st and there’s a grace period through the 5th, that notice goes out on the 6th. No exceptions. Even if the tenant says, “I’ll have it by the 15th,” your response is simple: “It’s my policy to serve the notice after the grace period. Everyone receives the same.”

Consistency keeps you out of legal trouble. In Cook County and Chicago, discrimination claims don’t just come from what you say—they come from how you enforce your policies. Uniformity is your shield. When tenants see that every missed rent gets a five-day, you’ll be amazed how quickly the pattern shifts—people start paying on time.

What a Proper Five-Day Notice Actually Looks Like

Let’s break it down like we’re training your office assistant from scratch. A five-day notice isn’t a threat—it’s a legal document that gives your tenant a final chance to pay before you file an eviction. Here’s what needs to be in it:

The full legal name of the tenant(s)
The complete address: include street, unit number, zip code—don’t skip
The total amount of unpaid rent owed as of the date you sign
Only include rent—unless your lease explicitly says that late fees or utilities count as additional rent
The statutory language required by Illinois law (don’t use a California form you found online—this isn’t Reddit advice)
Signature and date from you or your management company
Clearly state that they have five days to pay in full or the lease is terminated

Bonus tip: If your lease doesn’t state that all charges are “additional rent,” fix that now. Otherwise, you’re leaving money on the table during enforcement.

Service Matters More Than You Think

This is where most DIY landlords blow it. Serving a five-day notice in Cook County is like walking a legal tightrope. If you don’t do it right, the judge will toss your case before you even say your name.

Here’s how to serve it the right way:

Personal service is king. Hand it to the tenant directly. Or to any other occupant at least 13 years old who lives in the unit.
Certified mail? Risky. Unless you get a legible signature back (good luck with that), it won’t hold up.
Posting on the door? Only if the unit is abandoned. Judges will ask, “Did you attempt personal service?” If not, case dismissed.

In Chicago, you should make 8–12 documented attempts to serve in person. Write down the date, time, what you observed. “TV on, no answer. Dog barking, no response.” After that, you can post the notice, send it via email (if you have one), and back it up with regular mail.

GET A PROPERTY MANAGEMENT SERVICE QUOTE ESTIMATION

Is It Time to Use a Process Server?

We’ve started relying more on process servers, and for good reason. They’re professional, detailed, and judges respect their affidavits. It’s not just about checking a box—it’s about credibility in court.

Yes, it costs money. Around $75–$100 depending on the vendor. But what’s your time worth? If you’re spending four hours across three days driving to and from a South Side property from Evanston just to catch a tenant at home, you’ve already lost.

Even better? They document everything. If your case ends up in court, a process server affidavit is rock-solid.

But if you're in a time crunch, doing it yourself daily may still be faster. Just make sure you're documenting every attempt.

The Sneaky Risk of Partial Payments

This is the moment where many landlords lose their leverage. Your tenant offers you $300 on a $1,200 balance. It’s tempting. But here’s the problem: if you accept that partial payment, you void your five-day notice. You’ll have to start over from scratch.

Here’s how to protect yourself:

Turn off autopay immediately once you serve a five-day.
Don’t accept anything but full payment.
If they insist, reissue a new five-day notice for the remaining balance—immediately.

Pro tip: If a payment shows up in your lockbox or mailbox uninvited, return it with tracking. FedEx it back, same day. Keep the receipt. That’s your evidence in court that you didn’t accept the partial.

When Can You Actually File?

Now that the notice is served, the five-day clock starts. But here’s where landlords get tripped up again.

Let’s say you served it on the 15th. The tenant has five full calendar days to pay. That means you can’t file until the 21st.

Weekends count. But if Day 5 lands on a weekend or legal holiday, they get one extra business day to pay. No exceptions. You file early, your case gets dismissed. Don’t let your frustration cost you months.

The Long, Slow March Through Cook County Eviction Court

So, you served the notice. You waited the proper time. You’ve documented everything. Now you file… and the real wait begins.

In Cook County:

The filing fee is $356 (under $50,000 rent owed)
$61 per defendant for sheriff service (plus unknown occupants)
If sheriff fails, you’ll likely pay for a process server anyway

Oh, and your first court date? 60 days away. And if the sheriff fails to serve? You get to do it all again with a new summons. And when you finally show up to court? Get ready for another delay—thanks to the ERP (Early Resolution Program) requiring mediators to get involved.

Most of the time, your first appearance leads to a continuance, not a judgment.

Don’t Be Cheap. Be Strategic.

You can try to file the eviction yourself. You can spend hours in the clerk's office, pay the fees, handle the service. But if your lease is weak, your documentation sloppy, or your timeline off—you’re walking into a courtroom with a blindfold on.

If you’re hiring a legal team like KSN, they’ll need three things:

Your lease
An account ledger (clean and formatted, not scribbled on the back of an envelope)
A signed copy of the five-day notice

Then they’ll file, track it, and follow up. And you? You go back to being a landlord, not a litigator.

The Real Goal: Avoiding Evictions Entirely

Everything I just outlined? It’s your safety net. But the real win is never having to use it. And that’s where the magic of strong tenant screening comes in.

Here’s where you connect the dots:

Accurate rent pricing (get your Free Rent Analysis)
Thorough screening (need help? Try our Tenant Placement Service)
Consistent enforcement (use the same five-day policy every time)

Evictions are the symptom. Poor systems are the disease. Cure the system, and you never have to file again.

At GC Realty & Development, we’ve taken every one of these steps and baked them into how we manage properties across the Chicagoland area. Our team trains on this. We document it. We teach others how to do it. It’s how we’ve helped hundreds of landlords eliminate evictions from their portfolios.

Want to see where your rent stacks up? 👉 Run a Free Rent Analysis

Need someone to take tenant placement off your plate? 👉 Check out our Tenant Placement Service

Need Help Managing Your Chicago Property?

👉 Schedule a call with our team and learn how GC Realty & Development helps landlords win long-term

Or tune into the Straight Up Chicago Investor podcast and learn from the city’s best (and worst) investor stories. Because success is never a straight line. And we’re proof of that.

There is a lot of information contained here if you plan on investing in real estate locally. It may seem overwhelming for those wanting to invest in the Chicago market, but it is really just a team sport. Who is on your investing team? Do you even have a team? GC Realty & Development, LLC. has a dedicated team of professionals that are willing to share their decades of experience in all facets of real estate. We handle everything from Brokerage, Leasing and Property Management. Whether you hire us or not, we are happy to provide you with our resources and expertise.

What gets me up in the morning and keeps me going twelve hours a day is the ability to add value to local area investors, in Chicago and beyond! Those who connect with me often hear me say that our goal is to bring value to everyone we come in contact with. We hope that in return, they will one day hire us for our Tenant Placement,or Property Management Services, refer us to someone they know, or leave us a review about our services. We would clearly love all three, however, we are happy whenever we get the opportunity to help!

Reach out today!