Most of the time when someone calls our office, it's because something has gone wrong.

I'm Jason Marcordes, founder of Landmark Property Management, and after years of helping rental property owners throughout Chicago and the surrounding suburbs, I've learned those conversations usually start the same way. Everything was going well until it wasn't.

When rent is being paid, maintenance requests are routine, and lease renewals are signed on time, property management can almost seem easy. It's when something unexpected happens that owners start looking for answers.

One of the most common conversations we have is with owners whose tenants have stopped paying rent.

Sometimes it's after the first missed payment. Other times, an owner has spent months trying to work things out before deciding it's time to get another opinion. By then, unpaid rent is usually only part of the problem. The mortgage still has to be paid. Property taxes and insurance haven't gone away. Maintenance requests continue to come in. And if utilities are included in the lease, those bills keep showing up every month too.

Eventually, almost every owner asks me the same question.

"Can I just shut off the utilities?"

I understand why they're asking because when you're paying every expense associated with a property while receiving little or no rental income, it's easy to focus on the bills you can actually control. Another utility bill arrives, and it feels like one more reminder that the property isn't performing the way it was supposed to.

By the time someone asks me about shutting off the utilities, though, we're usually talking about something much bigger than a utility bill.

We're talking about a rental property that has stopped generating income, and an owner who's trying to figure out the smartest way to move forward. Instead of answering the question immediately, I usually ask one of my own.

"What happened?"

Start With the Conversation, Not the Conflict

One of the biggest mistakes I see landlords make is assuming every tenant who falls behind on rent belongs in the same category.

That's almost never the case.

I've worked with tenants who had always paid on time until they lost a job, went through a divorce, faced a medical emergency, or had another unexpected expense that completely disrupted their finances. I've also worked with tenants who stopped communicating altogether and never had a realistic plan for catching up. Those situations may look similar on a rent ledger, but they're completely different when you're deciding what to do next.

That's why, as soon as a tenant misses a payment, our first priority is starting a conversation.

We reach out by phone, text, email, and every reasonable method available because we're trying to understand what's really happening. In the video, I explain that we're trying to determine whether we're dealing with an income issue or an expense issue, and there's an important difference between the two.

If it's an expense issue, the tenant may have run into a one-time financial setback. Maybe their car needed a major repair, they had unexpected medical bills, or another emergency temporarily disrupted their finances. Income is still coming in, but they need a little time to recover. In those situations, it's often possible to create a payment plan that works for everyone. We talk through when their next paycheck is coming, how much they can realistically pay, and what it will take to become current.

If it's an income issue, the conversation becomes much more difficult. When someone loses their job, you're no longer talking about catching up on last month's rent. You're trying to understand how they're going to pay rent going forward. Are they interviewing? Do they have another position lined up? Is there a realistic timeline for getting back to work? Those answers matter because even if someone finds a new job tomorrow, it may still be several weeks before they receive their first paycheck.

Once we understand the situation, we can decide what makes the most sense. If we believe a tenant is going through a temporary hardship and has a realistic plan to recover, we always recommend trying to work it out if possible. I say that because replacing a good tenant is expensive. Vacancy, maintenance, cleaning, marketing, leasing, and the time it takes to find another qualified resident all cost money. Rental property is really hard to make cash flow when you're turning over tenants frequently, so if someone has been a responsible tenant and simply hit a rough patch, working with them is often the better long-term business decision.

The key is making sure there's an actual plan. When we agree to a payment arrangement, we aren't looking for general promises. We want specific dates, specific amounts, and clear expectations that are documented in writing so everyone understands exactly what's expected moving forward.

Unfortunately, not every situation ends that way. Sometimes the conversations become less productive. The explanations change, but the balance continues to grow. Payment dates come and go, communication becomes inconsistent, and it slowly becomes clear that the tenant doesn't have a realistic path to catching up.

That's when the conversation starts to change. Instead of asking how to help the tenant get back on track, you're asking what's best for the property moving forward.

Knowing When It's Time to Change Direction

If there's one part of this process that's difficult, it's knowing when to stop trying to solve the problem with another conversation. Most landlords don't struggle with whether they want to help a tenant. They struggle with deciding how long they should keep trying.

I've talked with owners who gave a tenant another month because they believed things were about to turn around. The tenant had a job interview scheduled. They were waiting to hear back from a new employer. They expected another source of income to come through soon. Every update sounded encouraging enough that giving them a little more time felt like the right decision.

Sometimes it is.

I've seen tenants work through a difficult period, catch up on rent, and remain in the property for years afterward. Those are great outcomes because everyone benefits. The owner avoids an expensive turnover, and the tenant gets the opportunity to recover from what turned out to be a temporary hardship.

The difficult situations are the ones where nothing is really changing. The explanations change. The promises change. The expected payment date changes. But if you step back and look at the situation objectively, the balance continues to grow, the tenant isn't any closer to becoming current, and there still isn't a realistic plan for how they're going to catch up.

At that point, I stop focusing on what the tenant says they're going to do and start paying attention to what they're actually doing.

Are they communicating consistently? Have they followed through on the commitments they've already made? Is the balance moving in the right direction, even if it's happening slowly? Those questions usually tell me much more than another explanation about why this week's payment didn't arrive.

One thing I never want owners to feel is that they're choosing between being compassionate and making a good business decision.

Those aren't opposite ideas. You can genuinely care about what someone is going through while also recognizing that your rental property has to be managed responsibly. In fact, I think the best landlords I've worked with do exactly that. They give people an opportunity to recover when it makes sense, but they also recognize when continuing to wait isn't improving the situation for anyone.

If a tenant doesn't have a realistic path to becoming current, waiting another month usually doesn't make the outcome better. It simply means another month of unpaid rent, another month of carrying costs, and another month before the property can begin producing income again.

One of the comments I hear most often from prospective clients is, "I wish I would have called sooner."

Very rarely does someone tell me they acted too quickly. Much more often they tell me they knew things weren't getting better, but they kept hoping next month would be different. I understand that feeling. If you've built a good relationship with a tenant, you want things to work out. Nobody enjoys having difficult conversations, and nobody wants to put someone through an eviction if there's another reasonable solution.

Eventually, though, the conversation changes.

Instead of asking how the tenant is going to catch up, you have to start asking what's best for the property moving forward.

That's usually the point where owners begin asking about shutting off utilities, changing the locks, or finding another way to regain possession of the property.

I understand why those questions come up, especially after months of unpaid rent.

The problem is that frustration is rarely the best place to make an important decision.

Before you decide what to do next, it's important to understand that the rules aren't the same everywhere.

We manage properties throughout Chicago and the surrounding suburbs, and where your rental property is located matters. Depending on the property, you may be subject to Illinois law, the Chicago Residential Landlord and Tenant Ordinance (RLTO), the Cook County Residential Tenant Landlord Ordinance (RTLO), or other local requirements. Advice you read online may be completely accurate for someone else's property while being completely wrong for yours.

That's why I always encourage owners to slow down before taking action.

Once you understand the rules that apply to your property, you can make a decision based on facts instead of frustration.

And that's where we start talking about your options.

So, What Are Your Options?

By the time we reach this point, we've usually answered the biggest question.

We've figured out whether the tenant is dealing with a temporary hardship or whether it's time to move in a different direction. From there, I tell owners they generally have three options. The first is continuing to work with the tenant.

If there's open communication, a realistic payment plan, and a genuine belief that the tenant will recover, that may still be the best business decision. People sometimes assume that replacing a tenant is automatically the better option, but that's not always true. Every turnover comes with vacancy, cleaning, maintenance, leasing costs, and the time it takes to find another qualified resident. If a good tenant is going through a temporary hardship, keeping that tenant is often less expensive than starting over.

The second option is beginning the legal process.

This is where I always encourage owners to understand the rules before taking action. In my video, I explain that for non-payment of rent, the process typically begins by serving the appropriate notice required under the applicable law before an eviction case can move forward. The exact notice requirements, timelines, and procedures depend on where the property is located, which is why it's important to understand the local rules and work with an attorney who regularly handles landlord-tenant matters in that area.

One detail that surprises many owners is that the way you handle payments after serving a notice can affect the legal process. In Illinois, accepting a partial rent payment after serving certain non-payment notices may impact your ability to proceed based on that notice. That's one of many reasons I encourage owners not to guess their way through an eviction. A small mistake at the beginning can create delays later.

Another misconception is that filing an eviction means the problem is almost over. It isn't.

Filing is simply the beginning of the legal process. How long it takes depends on the county, the court, and the specific circumstances of the case. Some cases move much faster than others, but regardless of the timeline, I encourage owners to go into the process with realistic expectations rather than assuming they'll have possession of the property again in a few weeks.

That's also why I tell owners not to make decisions based on Facebook comments or advice from strangers online. Every time someone asks what to do about a tenant who hasn't paid rent, you'll see suggestions like shutting off utilities, changing the locks, or finding another way to force the tenant to leave.

I understand the frustration behind those comments.

I also know that frustration doesn't change the law.

Kristy spends a lot of time helping owners understand compliance because we've seen how expensive small mistakes can become. Using the wrong notice, overlooking a local ordinance, or trying to shortcut the legal process often creates more problems than it solves.

Once owners understand that, the conversation naturally turns to one final option that many people haven't considered. Cash for Keys.

The Last Option I Talk Through With Owners

The last option I talk through with owners is something called Cash for Keys.

I'll be honest, this is usually where I get the most pushback.

The first question is almost always the same.

"Why would I pay someone who already owes me money?"

I completely understand that reaction because it's the same one most owners have the first time they hear about it. In the video, I say, "This one hurts. I get it. No one wants to reward a tenant for not paying their rent." That's exactly how it feels.

The reason I still bring it up is because by the time we're having this conversation, I'm no longer looking at the situation emotionally. I'm looking at it as a business decision.

Let's use a simple example.

If your property rents for $2,000 a month and it's going to take several more months before you regain possession through the legal process, the losses continue to add up every month you're waiting. Once you finally have the property back, you still need time to inspect it, complete any repairs, clean it, market it, show it, screen applicants, and place a new tenant. Even in the best-case scenario, that's additional time before the property starts producing income again.

Now compare that to reaching an agreement where the tenant voluntarily moves out.

You may not like writing that check, but the question isn't whether you like it. The question is whether paying a few thousand dollars today costs less than continuing to lose rent while waiting for the legal process to play out.

That's why I don't look at Cash for Keys as rewarding bad behavior.

I look at it as comparing two business decisions and choosing the one that leaves the owner in the strongest financial position. Sometimes that's still eviction. Sometimes it isn't.Another benefit owners don't always think about is the condition of the property when it's returned.

One of the reasons we like clear, written agreements is because everyone understands the expectations before the tenant moves out. In the video, I explain that we typically expect the property to be returned in good condition and broom swept before payment is made. Compare that to a contested eviction, where emotions are often running high, and it's easy to understand why the condition of the property can be very different.

Like everything else we've discussed, this isn't something I'd recommend handling with a handshake. The agreement should be documented properly, and I always recommend involving an attorney so the terms are prepared correctly. In the video, I also mention using a cashier's check or money order instead of cash so there's a clear record of the transaction.

Cash for Keys isn't the right answer every time.

Neither is a payment plan.

Neither is eviction.

The right answer depends on the tenant, the property, the circumstances, and the laws that apply where your rental is located. That's why I spend much more time understanding the situation than trying to fit every owner into the same solution.

What I Hope Owners Take Away From This

When someone calls our office because a tenant hasn't paid rent, they usually think they're calling with a utility question. By the end of the conversation, we've almost always moved past that. We're talking about whether the tenant has a realistic path to catching up, what the local laws require, and which option puts the property in the best position moving forward.

After years of managing rental properties, I've realized this business is about much more than collecting rent or coordinating maintenance. Those responsibilities are important, but they aren't the reason owners pick up the phone. They call because they're facing a situation that doesn't have an obvious answer, and they want another perspective before making an important decision.

Sometimes the right answer is giving a good tenant the opportunity to recover from a temporary hardship. Sometimes it's beginning the legal process because the situation simply isn't improving. Other times, it's having a difficult conversation about Cash for Keys because, from a business standpoint, it's the option that makes the most financial sense.

My job isn't to force every owner toward the same solution. It's to understand what's happening, explain the options, and help owners make informed decisions based on the facts instead of the frustration they're feeling in the moment. That's the approach we've always taken at Landmark Property Management, and it's the same advice I'd give if we were sitting across the table talking about your property.

Talk Through Your Situation With Us

If you're dealing with a tenant who has stopped paying rent and you're not sure what your next step should be, we'd be happy to help.

At Landmark Property Management, we've worked with rental property owners throughout Chicago and the surrounding suburbs for years, and we've had this conversation countless times. While we don't provide legal advice, we can help you think through the situation, explain the options available to you, and share what we've seen work in circumstances like yours.

Whether you ultimately decide to hire Landmark or simply want another perspective before making an important decision, we're always happy to be a resource.

If you'd like to talk through your situation, schedule a free consultation or call us at (312) 313-8553. We'd be happy to learn more about your property and discuss the next steps.

Frequently Asked Questions

Can I shut off utilities if my tenant hasn't paid rent?

In most situations, no. If utilities are included as part of the lease, intentionally shutting them off to pressure a tenant into leaving can create serious legal problems. While every situation is different, landlords should avoid "self-help" eviction tactics and instead follow the legal process that applies to their property. If you're unsure of your rights or responsibilities, it's best to consult with a qualified landlord-tenant attorney before taking action.

How long should I work with a tenant before starting the eviction process?

There's no universal timeline because every situation is different. The better question is whether the tenant has a realistic plan to become current. If they're communicating, following through on payment agreements, and making measurable progress, it may make sense to continue working with them. If the balance continues to grow and there's no realistic path forward, it may be time to begin the legal process.

Can I accept a partial rent payment after serving a notice?

Be careful. In Illinois, accepting a partial rent payment after serving certain non-payment notices may affect your ability to continue with the eviction process based on that notice. Because the rules can be complicated, it's important to understand the legal consequences before accepting any payment and to consult with an attorney if you're unsure.

How long does an eviction take in Chicago?

There isn't one answer. The timeline depends on the county, the court, and the specific facts of the case. In our experience, owners are often surprised by how long the process can take, which is why acting promptly and following the correct legal procedures from the beginning is so important. An experienced landlord-tenant attorney can provide guidance based on your property's location and circumstances.

What is Cash for Keys?

Cash for Keys is a voluntary agreement where a property owner offers a tenant financial assistance in exchange for moving out by an agreed-upon date and returning the property according to the terms of a written agreement. While it isn't the right solution for every situation, it can sometimes help owners regain possession sooner, reduce vacancy costs, and minimize property damage compared to a lengthy eviction.

Is it better to work with a tenant or file for eviction?

That depends on the situation. If the tenant is experiencing a temporary hardship, communicating openly, and has a realistic plan to catch up, working together may be the best long-term business decision. If the tenant has stopped communicating or there's no realistic path to becoming current, it may be time to begin the legal process. The goal isn't to choose the same solution every time. It's to choose the solution that makes the most sense for the circumstances.

Are eviction laws different in Chicago than the rest of Illinois?

Yes. While Illinois state law provides the framework for landlord-tenant relationships, additional local ordinances may apply depending on where your property is located. For example, rental properties in Chicago are generally subject to the Chicago Residential Landlord and Tenant Ordinance (RLTO), while many suburbs in Cook County fall under the Cook County Residential Tenant Landlord Ordinance (RTLO). Properties in other counties may be subject to different local requirements. Before taking action, make sure you understand the rules that apply to your specific property.

Should I hire a property manager before problems arise?

Many owners don't contact a property manager until they're dealing with a difficult tenant, but professional management can often help prevent those situations from developing in the first place. Thorough tenant screening, consistent rent collection, proper lease enforcement, proactive communication, and staying current with changing landlord-tenant laws all reduce the likelihood of costly problems down the road.

Can Landmark Property Management help if I'm already having problems with a tenant?

Yes. We regularly speak with rental property owners who are trying to figure out what to do after a tenant stops paying rent or violates the lease. While we don't provide legal advice, we can help you evaluate your situation, explain the property management side of the process, and discuss the options available to you. If legal action is necessary, we can also help coordinate with experienced landlord-tenant attorneys as part of the management process.

Can a property manager evict a tenant?

A property manager can coordinate the eviction process, serve required notices where permitted, communicate with the owner, and work alongside a landlord-tenant attorney. However, property managers are not attorneys and cannot provide legal advice or represent owners in court. At Landmark, we help guide owners through the process while coordinating with experienced legal counsel when necessary.

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