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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Evictions are one of those parts of Chicago real estate that no one plans for, but almost everyone eventually faces. You can screen well, communicate clearly, and still find yourself dealing with a resident who stops paying and stops responding. When that happens, the Cook County eviction process becomes less about fairness and more about understanding timelines, procedures, and how to minimize losses.
In this episode of the Straight Up Chicago Investor Podcast, eviction attorney Zeke McDonald-Lewis walks through the Cook County eviction process from start to finish. The recurring theme is simple, this is not about being right, it is about making smart business decisions, getting possession back, and moving forward.
What You’ll Learn in This Episode
Chicago landlords will learn why notices and service are the foundation of the eviction process, how ERP impacts timelines, when settlements make sense, and why chasing money judgments is often unrealistic. Zeke also explains why sealed evictions change how landlords should think about screening and why squatters are usually handled through the same civil process as non-paying tenants.
Questions We Answer in This Episode
Q. What mindset should landlords have when starting an eviction?
A. Evictions are business decisions, not moral battles. The goal is possession and stopping losses, not proving a point.
Q. When does settlement make more sense than going through the full eviction?
A. Most of the time, especially when the tenant is communicating and willing to sign a court-entered agreement.
Q. What payment plan mistakes do landlords make?
A. Plans that start weeks later with no money up front usually fail and put landlords back at square one.
Q. What is the biggest mistake new landlords make with notices?
A. Serving the wrong notice, listing the wrong tenants, using the wrong unit number, or serving it improperly.
Q. Can landlords accept partial payments after serving a five-day notice?
A. No. Accepting partial payment can invalidate the notice and force the process to restart.
Q. How long does a typical Cook County eviction take?
A. Most cases take five to eight months depending on tenant behavior, service, ERP, and court delays.
Q. What is ERP and how does it affect cases?
A. ERP provides legal access and can help secure rental assistance when funding exists, but often adds delay when it does not.
Q. What happens if the tenant does not show up to court?
Many cases resolve by default, but sheriff enforcement still takes time and can be paused by motions.
Q. Are money judgments usually worth pursuing?
A. Usually no. The money owed is more often a bargaining chip than a collectible asset.
Q. How are squatters handled in Chicago?
A. Squatters are typically handled through the same eviction process, not a faster criminal route.
Show Notes
00:00 Why evictions are business decisions, not justice battles
03:25 Housing provider tip on realistic payment plans
11:37 Why notices are the most common failure point
17:04 Serving five-day notices correctly in Illinois
21:08 The danger of accepting partial payments
24:51 ERP explained and when it helps
28:37 Sealed evictions and screening risks
32:02 Why money judgments rarely pay off
36:00 Why settlements must be court-entered
44:09 Fraud and squatter horror stories
46:49 Squatters and civil possession
55:42 Advice for new Chicago investors
Key Takeaways for Chicago Landlords
Evictions are about speed and process, not principle.
Mistakes at the notice stage cost months.
Partial payments can invalidate your case.
ERP helps most when rental assistance exists.
Court-entered agreements are the only enforceable settlements.
Money judgments are usually leverage, not income.
Squatters require fast action and realistic expectations.
Guest Name: Zeke McDonald-Lewis
Guest Company: Erwin Law
Guest Link: https://erwinlawfirm.com/attorney/ezekial-mcdonald-lewis/
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
