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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Tim finally got his hands on the first full draft of Mayor Johnson’s Protecting Renters Ordinance, so this week we went past the headlines and into the actual details being discussed.
Some parts of the proposal surprised me. There are actual tenant responsibilities and consequences for blocking lawful access. But there are also new fee limits, longer notice requirements, and relocation payments that could completely change how Chicago landlords handle renewals and possession of their properties.
We also talked about where investors are looking on the South Side and one of the biggest changes we are seeing in the 2026 Chicago rental market.
YouTube Link
https://www.youtube.com/watch?v=r_R2mkgWIT4
Proposed CRLTO Details
The first surprise in the proposed CRLTO was seeing actual tenant responsibilities written into the draft.
Tenants would be responsible for properly disposing of garbage, keeping plumbing fixtures clean, reasonably using building systems, not deliberately damaging the unit, and not interfering with another resident’s peaceful enjoyment.
The proposed access rules also caught our attention. Landlords would still generally need 48 hours' notice for non-emergency entry, and entry would need to happen during reasonable hours. But tenants who improperly block lawful landlord access could potentially face fines of $50 to $100 per day.
On the landlord side, improper entry could create penalties of $250 to $750.
The proposal also gets much stricter around timing. Any rent increase could require 120 days' notice, while a renewal without an increase could require 90 days' notice.
Fees would change too. The proposed Chicago application fee cap would be $20 or actual cost, whichever is lower. Landlords could charge either a one-time pet fee or a recurring pet fee, but not both. Move-in fees, optional services, and utility charges would also need to be tied closely to actual costs.
Then we got into the biggest issue: just cause eviction and relocation payments.
Based on the draft Tim reviewed, nonpayment and serious lease violations would not require a relocation payment. A tenant rejecting a legitimate rent increase could also result in zero relocation payment.
But owner move-in, condo conversions, major repairs, CHA abatement, and demolition could require five months of rent or $5,000, whichever is higher.
Anything that falls outside the listed reasons could trigger 10 months of rent or $10,000, whichever is higher.
That catchall is where the proposal becomes very concerning for landlords.
Investing On Chicago’s South Side
We also talked about whether South Side investor interest is heating up or cooling down.
The answer is completely neighborhood dependent.
South Shore had years of investor hype tied to the Obama Center. Now some of that initial excitement has cooled as the project becomes reality.
Woodlawn is different. We are seeing properties sell for numbers that would have surprised a lot of investors just a few years ago.
Then there are areas like East Side and Hegewisch that do not get nearly as much attention.
The East Side has reasonably priced housing, the alphabet streets, Metra access, established communities, and commercial corridors where we are seeing more restaurants and businesses show up.
Hegewisch is another unique pocket. It almost feels like an island because of how separated it is geographically from surrounding neighborhoods.
The point is something Tim and I say all the time: Chicago is block by block.
Saying you invest on the “South Side” is not enough. Two streets can completely change the property, tenant base, rent, and long-term opportunity.
2026 Chicago Leasing
One of the biggest changes I am seeing in the 2026 leasing market is the growing difference between updated and outdated rental units.
A few years ago, an updated unit might get $25 or $50 more per month.
Now we are seeing differences of $150 to $250 in some cases, and the updated units are leasing faster.
White cabinets, clean flooring, modern finishes, and a unit that feels current are becoming much more important to renters.
Putting money back into the property can directly put more money back into your account.
Tim also brought up the changing voucher market.
A few years ago, finding a subsidy tenant on the South Side was usually not the hard part. The paperwork and inspection timeline were the problem.
Now, families who previously had three-bedroom vouchers may have smaller vouchers and less buying power. That is changing demand for larger units and creating another challenge for landlords who historically relied heavily on voucher tenants.
The Chicago leasing market is still active, but renters are becoming more selective and the subsidy market is changing. Owners need to understand both before deciding how much to invest in a unit and how to price it.
Questions We Answer in This Episode
Q: Could tenants be fined for refusing landlord access?
A: Under the proposed ordinance discussed in the episode, tenants who improperly block lawful access could face daily fines.
Q: How much notice could Chicago landlords need for a rent increase?
A: The proposed CRLTO would require 120 days' notice.
Q: Could landlords owe relocation payments to regain possession?
A: Yes. Depending on the reason, the proposed payments could reach five or 10 months of rent.
Q: Where are investors looking on the South Side?
A: Woodlawn remains active, while East Side and Hegewisch are getting more attention.
Q: What is changing in Chicago leasing in 2026?
A: Updated units are commanding larger rent premiums and leasing faster, while voucher tenants are seeing changes in buying power.
Show Notes and Timestamps
00:55 First draft of the Protecting Renters Ordinance revealed
05:03 Tenant responsibilities inside the proposed CRLTO
06:24 Fines for blocking lawful landlord access
11:07 120-day rent increase notice requirements
12:28 Application fee and pet fee restrictions
15:39 Tenant repair rights increasing to $1,500
20:30 Just cause eviction relocation payments explained
23:30 Rent increases and when relocation fees may not apply
36:26 Biggest changes in the 2026 Chicago leasing market
38:46 South Side investing, Woodlawn, East Side, and Hegewisch
Key Takeaways for Chicago Landlords and Investors
The proposed CRLTO includes new responsibilities and penalties for both tenants and landlords.
Renewal and rent increase decisions may need to happen much earlier.
Just cause relocation payments remain the biggest concern in the proposal.
South Side investing is completely block by block.
Updated units are earning larger rent premiums and leasing faster in 2026.
Changes in the voucher market are affecting demand for larger rental units.
Guest Information
Mark Ainley
Founder & Partner – GC Realty & Development
Podcast Co-Host – Straight Up Chicago Investor
Tim Harstad
Founder – Chicago Style Management
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
