How to Deal with Problem Tenants in Chicago (and the Suburbs)

Being a landlord in Chicago isn’t easy—especially when you’re stuck with a tenant who won’t pay rent, damages your property, or refuses to leave. If you’re feeling overwhelmed or drained by a bad rental situation, you’re not alone.

We help landlords across Chicago and the surrounding suburbs get out from under problem properties fast. Fill out our online form or call/text us at (773) 825-9855 to request a cash offer today!

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Understanding Chicago’s Tenant-Friendly Laws

Chicago and Cook County have strict protections in place for tenants, which can make it incredibly difficult for landlords to act quickly. If you're unfamiliar with the process, eviction can become a costly legal nightmare.

You must provide proper notice, follow legal procedures exactly, and be prepared for delays. “Self-help” eviction tactics—like changing the locks or shutting off utilities—are illegal and can backfire. And in many cases, court backlogs mean the process can take months.

How to Know You Have a Problem Tenant

Sometimes it’s obvious. Other times, the signs creep in gradually. If you’re dealing with constant late rent, unauthorized guests, property damage, or a tenant who avoids communication—or worse, becomes aggressive—it’s likely time to explore your options.

Problem tenants rarely improve over time. And in Chicago, the longer the issue goes on, the more difficult and expensive it becomes to resolve.

What Are Your Options as a Landlord?

As a landlord, you typically have three paths forward when dealing with a difficult tenant:

1. Offer “Cash for Keys”
This means offering your tenant a lump sum of money to move out voluntarily. It might sound crazy—but it often works and is cheaper and faster than eviction. We can even help with this negotiation.

2. Go Through Formal Eviction
If your tenant refuses to leave, you can file for eviction in court. But in Chicago, this process is slow and expensive. You’ll need legal counsel, time, and patience.

3. Sell the Property As-Is—Tenant Included
This is the simplest option for many landlords. We buy rental properties with tenants still inside. Whether they’re paying or not, cooperative or not, we handle it. You get paid, and we take over the problem.

Sell Your Chicago Rental—Even with the Tenant Still There

We’ve helped dozens of landlords across Chicago and the suburbs walk away from problem properties with zero stress. You don’t need to wait for an eviction, make repairs, or negotiate with a tenant who refuses to cooperate.

We’ll buy your property as-is, handle all communication with the tenant, and close on your timeline.

  • We buy with tenants still inside

  • No eviction needed

  • We pay cash and close fast

  • No cleaning or repairs required

  • You walk away stress-free

Get Your FREE Offer Started TODAY!

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What Other Happy Chicagoland Landlords Are Saying

"I’ve been a landlord in Berwyn for over 20 years, but my last tenant nearly broke me. Late rent and total disrespect. I reached out just hoping for options, and ended up selling the property with the tenant still inside. Couldn’t be happier."

Visual of fast and fair cash offers for homes in Chicagoland

Frank D. - Berwyn, IL

5-stars

“My tenant stopped paying rent and threatened to sue when I asked him to leave. I was ready to give up—then I found this company. They bought the property with him still in it, and I never had to speak to him again.”

Supporting homeowners through quick house sales in Chicagoland

Derek S. - Cicero, IL

5-stars

"I had a tenant in my two-flat in Logan Square who hadn’t paid rent in over four months and was refusing to leave. These guys stepped in and bought the property as-is—tenant and all. I was shocked at how easy they made it and how fast the process was."

Homeowners in Chicagoland turning properties into cash with ease

Maya T. - Chicago IL

5-stars
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We Help Landlords Across the Chicagoland Area

  • Cicero

  • Oak Lawn

  • Evanston

  • Skokie

  • Naperville

  • Joliet

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  • Elmwood Park

  • Waukegan

  • Gurnee

  • Oak Park

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