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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Top Landlords Are Doing This in 2025
There’s a quiet shift happening in Chicago right now. It was fairly easy to become an investor between 2018 and 2021. Interest rates were low, there was inventory, and rental rates were on the rise, even with the largest pandemic in over a century in the midst of it.
During this period you have major shifts in how Chicago Realtors are conducting business with the NAR settlement, Cook County RTLO and its debut, and a capped limit on what Wholesalers can do legally without being licensed.
The business of real estate investing in the Chicago market has become hard and those that know how to find deals and operate are the ones left in the game while others have stopped investing or put a long pause on trying to find their next deal.
The top investors that are left are not shouting on social media or bragging about cash-on-cash returns. They’re building stability. They’re growing smart. And they’re doing things very differently in 2025.
These are still great times for investors that know how to find deals, know how to pair capital even with higher rates, and Landlords that operate their rental portfolio like a business.
The most beautiful part of real estate is often highlighted around finding the deal or negotiating a killer purchase price. But, the money is made long term in the operation of the business.
The solid Landlord operators here in Chicago are not phased by the new laws, they are not worried about off season vacancy, rising cost of maintenance, or the continued hoops investors have to jump through just to screen an applicant.
If anything these new obstacles are something many investors, including myself, are excited about. This thins out the competition, separates the men/women from the boys/girls. These crazy market changes create headlines that detracts out of state investors from coming here. It creates opportunities!
They Know the Numbers Before the Emotions
The best landlords in Chicago are obsessed with numbers and not just cash flow. They know their operating expenses per unit. They understand return on equity, not just ROI.
They set the current rental rates, they have reduced vacancy, and they understand the 5 ways to make money with their properties.
Want to confirm you are setting the most competitive rental rate? Used the tools thousands of Chicago investors are using each year for reduced vacancy. Run a Free Rent Analysis..
They’re Proactive About Lease Renewals and Vacancy Timing
Here’s the dirty secret most average landlords won’t admit: their leases end at the worst possible times. January. February. Right after the holidays. And they wonder why they get crickets when they list.
The top landlords? They control their lease terms like a pilot controls altitude. They know July 31st is gold. They align renewals to summer demand. They offer 15-18 month leases when it allows the lease to end at the best time of the year. This isn’t just a nice-to-have—it’s a revenue move. One missed month of rent because of poor timing is a 9% loss on annual income.
People ask me often when is the worst time to end a rental lease in the Chicago market and I tell them it depends.
North & Northwest side of Chicago - You must end your lease no later than August 31st of any given year to ensure you have someone moving in by the end of September and even that is pushing it. If you can end the lease by end between April and May that is ideal. Marketing a rental in this side of the city between October-February will result in extended vacancy or rent reductions as much as 10-15% from peak rental season rates.
Southwestern, Western, and Northwestern Suburbs - There is less housing stock available from private owners in any given area so time of year is less of an urgent matter but you should still avoid having to go on the market October-January.
South & Southeast Side Of Chicago & South Suburbs - There is more volume of off rental season tenants out there and they often are able to move in quicker so if you have a rental in October or January it isn't the end of the world but you may be on the market a week or two longer.
You don't have to worry about when the tenant moves out, if you don't let them move out!
Lease Renewals
GC Realty & Development lives on and preaches the notion of “Don’t Anyone Move Out so do what it takes to renew them,”. Turnover is costly and risky and the best Chicago Landlords know this. The money is made in average lease months your residents stay so track that metric and improve it.
Work on your lease renewals early and remember there are rules about this in Chicago and Cook County.
60 Day Notice - If a tenant has been their 1-3 years
120 Day Notice - If a tenant has been there more than 3 years
For Kane, Will, Dupage, Lake, McHenry, and Kendall most likely your lease says 30 days but across the industry sooner the better is best practice but 30 days is the closest you should push it.
They Outsource What Slows Them Down
At some point, every serious landlord realizes they’re the bottleneck in their rental operations efficiency. Marketing a vacancy on time, showing the unit often enough, screening tenants thoroughly, and making repairs timely to ensure resident satisfaction. Often it works when they have one unit. But as you grow, it kills your time and your portfolio’s potential.
If you’re still DIYing every showing or screening tenants off gut feelings, that’s not hustle—that’s delay. Top operators don’t confuse busy with productive.
They Over-Communicate with Residents (Yes, Really)
The best landlords in Chicago aren’t just managers. They’re communicators. They know that a resident who feels respected and heard is also a resident who renews. They also allow space for the “Human to Human” interaction that this world craves these days. That means proactive check-ins, quick replies to maintenance requests, proactive notice of maintenance delays, and clear lease explanations. There is a good chance you were a renter at one time, think about how you wanted to feel.
It might sound soft, but here’s the reality: turnover is expensive. Every time a tenant moves out, you’re not just losing rent—you’re spending on cleaning, repairs, showings, and possibly another month or more of vacancy.
We like to look at it from the tenant perspective. Lease renewal really starts to move in. We broke down the moving process from the tenant's point of view with New York Times Best Seller Joey Coleman. (Watch Here)
They Stay Ahead of Compliance Instead of Chasing It
The rules in Chicago aren’t getting looser. The RTLO in Cook County, the CRLTO in Chicago, The Just Housing Amendment is enforced in Cook County suburbs. The enforcement climate has tightened—and the best landlords don’t just react to that; they plan for it.
Your leases should be reviewed annually, your screening criteria and process should be always updated. Things are always changing and it takes being in the know to stay out in front of it all.
Let’s be real, a Fair Housing violation or CRTLO case can crush two years of your properties profit. And a lawsuit over screening practices? That’s a risk not worth taking when compliance is 100% within your control.
They Budget for Repairs Before They’re Needed
Preventive maintenance isn’t exciting. But you know what’s worse than paying for a water heater? Paying for one after it floods the basement and you’ve got three damaged walls, mold remediation, and a furious tenant ready to break their lease.
Top landlords plan maintenance like clockwork. They know the age of every system. They build reserves into every deal. They’d rather replace something on schedule than get surprised by an emergency service call on a Sunday night.
They also don’t cut corners. Cheap repairs now almost always cost more later. They’ve learned this lesson the hard way—and you don’t have to. Your cut corners may not always affect your tenant today but it could affect your future sales price by thousands of dollars.
They Treat Their Portfolio Like a Business, Not a Side Hustle
This is the mindset shift that separates the top ten percent from the rest. Owning one or two properties might feel manageable on nights and weekends. If your goal is to scale, even modestly, then you need to treat your portfolio like an actual business.
That means tracking KPIs like the average time tenants stay in your units, outsource to other professionals when it makes sense, creating repeatable systems, and having standard operating procedures. The best landlords in 2025 are the ones who can step away for a week and know the lights stay on. That’s not luck, that’s business maturity.
They Know That “Passive” Income Isn’t Real
To find the best deals in the market investors know they can NOT just lean on their Realtor, they have to be out there looking and networking themselves. They also know that unless you hire a Property Management company the concept of “arm chair investment” isn't possible either.
There’s nothing passive about the effort that has to go into quality marketing and screening. Nothing passive about timing of renewals. Nothing passive about ignoring market shifts.
They Look Ten Years Out, Not Ten Months Ahead
The real winners in Chicago real estate aren’t chasing 2025 wins. They’re laying the groundwork for 2035. That means buying in the right zip codes, investing in solid properties, and thinking in decades, not quarters.
They’re not trying to hit a home run every time. They’re building consistency. Repeating wins. Avoiding big mistakes. Over time, that adds up to serious wealth.
The best properties I personally own today are the ones I have had for the longest. They were not the best though in 2008. Investors know that time is the real asset!
You Don’t Have to Be a Veteran to Operate Like One
This is where it gets exciting. You don’t need 20+ years of experience like me to start thinking like a top landlord. You just need the right systems, the right mindset, and the willingness to take action.
Start with the basics:
Run a Free Rent Analysis to make sure your pricing is on point.
If you are too busy to handle Tenant Placement use a service like ours.
Align lease terms to peak season.
Track every dollar that goes in or out.
Talk to your tenants like you want them to stay.
In the end of the day if you want to invest but don't want to have to be the investor we described here then hire someone like GC Realty & Development to handle it all for you.
And then keep building from there.
Because in 2025, the Chicago market is still one of the best cities in the world for rental real estate! You just have to know the right people and operate like the best operators do.
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!
Partner / Co Host of Straight Up Chicago Investor Podcast
