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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Let me give you a little history before I get into the three moves, because the timing of this matters more than most landlords realize.
After the Great Recession, the Chicagoland leasing market spent years without any real rhythm. Then somewhere in the late 2010s it came back to what I would call a historically normal rental season, which around here means April through Labor Day. That is your window. That is when the volume of renters actually moving is high enough to support market rents and reasonable days on market.
Then Covid hit and threw the whole thing off again. For a few years we were leasing units in months we normally would not have, and the season stretched and warped in ways that made planning almost impossible.
In 2025 we finally got the closest thing to a normal season we have had in years. April through Labor Day was strong, and then the leasing season fell off exactly the way it historically does. That drop off is not a surprise anymore. It is the pattern returning.
So here is my point. We are doing everything we can right now across our portfolio to be on the right side of that drop off. I want you doing the same thing. The landlords who panic in September and October are almost always the landlords who did nothing in August. There is still real demand out there for the next few weeks. After that it thins out fast, and a unit that misses the window does not sit for thirty days. It sits until spring.
Three things. Do them now.
Key Takeaways
The Chicagoland leasing season runs April through Labor Day, and 2025 confirmed that pattern is back after years of Covid distortion.
If your unit is vacant right now, price it to be in the top half of your competition today rather than chasing the market down twenty five dollars at a time.
Count your actual competition. If ten similar units are available in your neighborhood and five rent this weekend, you need to be in the top five to get leased.
For a September or October move in, write a 15 to 18 month lease so the term ends in February or March when the market is already climbing again.
If your unit is still occupied and the resident is leaving in September, start preleasing now while they are still living there.
Preleasing requires resident cooperation and a unit that shows well, which is why saving your marketing photos from the last leasing round pays off.
1. Reduce Now and Do Not Chase the Market Down
The most expensive mistake I see in August is the slow reduction. A landlord lists at a number, gets no traction, drops twenty five dollars after two weeks, gets no traction, drops another twenty five dollars two weeks later. He feels like he is being disciplined. What he is actually doing is trailing the market the entire way down, always priced for the demand that existed a month ago, never priced for the demand in front of him.
By the time that landlord catches up to the market, the season is over and he is negotiating in October against a much smaller pool of renters.
Do the opposite. Make one meaningful reduction now that puts you in the top half of your competition, and then hold it.
Here is how to figure out what that number is, and it takes about thirty minutes.
Go look at what is actually available. Not what you think your unit is worth. Not what you rented it for two years ago. Pull up every comparable active listing within a reasonable radius of your property, and count them. Then look at what has rented recently and at what price, and how long those units sat before they leased.
Now run the arithmetic that matters. Say there are ten comparable units available in your neighborhood and five of them are going to get leased this weekend. To be one of those five, you have to be more attractive than half the field. That is the whole game. Price is the fastest lever you have, but it is not the only one. Photos, condition, how quickly you respond to an inquiry, and how easy you make it to see the unit all count toward being in that top half.
Ask yourself honestly where your unit ranks in that group of ten. If the answer is sixth or seventh, you are not getting leased this weekend, and you are not getting leased next weekend either.
If you would rather not do that homework yourself, or you want a second opinion on the number you land on, request a Free Rental Analysis from our team. We are pricing units across Chicago and the suburbs every week, so we are not looking at last year's comps or a Zestimate. We are looking at what is actually leasing in your neighborhood right now and what it is leasing for. It takes seconds to request and it costs you nothing, and knowing the real number is what lets you make one decisive reduction instead of six small ones.
Before you decide how much to cut, also run the numbers through our Vacancy Loss Calculator. Landlords consistently overvalue the monthly rent and undervalue the vacant month. Seventy five dollars a month is nine hundred dollars over a year. One vacant month on a two thousand dollar unit is two thousand dollars, and that is before you account for utilities, lawn care, snow removal, and the risk that comes with an empty property in Chicago through the winter. The calculator makes that tradeoff obvious in about a minute, and it will usually tell you to reduce more aggressively than your gut wants to.
2. Take Your Lease End Date Into Consideration
This is the one almost nobody thinks about, and it compounds year after year.
If you lease a unit in September or October and you write a standard twelve month lease, you have just guaranteed that your next turnover happens in September or October of next year. You have locked yourself into the worst part of the calendar permanently. Do that a few times across a few properties and you have built a portfolio that turns over exactly when demand is at its weakest.
So do not write twelve months. For a September or October move in, write a 15 to 18 month lease and land that expiration in February or March.
I know February and March sound early to some people, and that is exactly why I like them. The leasing market is already on the upswing by then. Renters are starting to look, activity is building, and you are getting your unit in front of that demand before the field gets crowded. By June you are competing against every other listing in the neighborhood. In February and March you are competing against far fewer, with a renter pool that is real and growing. You get better attention, faster showings, and you are set up to be leased and stabilized heading into the strongest months of the year rather than scrambling through them.
Residents are generally fine with a longer term. Many prefer it, because it means no renewal conversation and no increase for a longer stretch. If you need to sweeten it slightly to get the longer term signed, do it. The value of moving your expiration date out of a dead month and into a live one is worth far more than a small concession.
Same thinking applies to renewals you are working on right now. If you have a resident with a December, January, or February expiration, that is a problem you should be solving in August, not in November.
3. Prelease the Unit That Is Still Occupied
If your unit is occupied and you already know the resident is leaving, or they do not move out until September, do not wait for the keys before you start marketing. Start now while they are still living there. We call it preleasing, and it is the difference between zero days of vacancy and sixty.
There are two requirements, and both are real.
First, you need the resident's cooperation. You are asking to bring strangers through their home while they still live in it, and you need to handle that like the favor it is. Give plenty of notice, be respectful of their schedule, follow whatever entry notice your local ordinance requires, and consider a small incentive for making it easy. A resident who feels steamrolled will make showings miserable and can cost you the lease.
Second, the unit has to show well. This is where a lot of landlords get stuck, because a lived in unit does not photograph like a rent ready one. If you saved your marketing photos and video from the last leasing round, you are in great shape. Use those to market the unit and use the in person showing to confirm condition. If you did not save them, learn from it this time around and save everything before your next turnover. Good photos of an empty, clean unit are an asset you should be able to reuse.
If the resident will not cooperate or the unit truly cannot be shown, you still are not powerless. Get your listing up with the old photos and an accurate available date so you are collecting inquiries and building a waiting list. Book showings for the first days after move out. You will not eliminate the vacancy, but you can cut it substantially.
Put It Together
None of these three moves require money. They require you to make a decision in the next two weeks instead of the second week of October.
Price to be in the top half of your competition today. Write your new lease so it expires in a month you actually want to be leasing in. Market occupied units before they are empty.
The landlords calling me in October are not calling because the market turned on them. The market did what it does every single year. They are calling because they spent August hoping.
Frequently Asked Questions
When exactly does the Chicagoland leasing season end?
Practically speaking, Labor Day. Demand starts thinning noticeably after that, and by mid October you are dealing with a much smaller and generally more difficult applicant pool. There are always renters moving in the fall, but there are not enough of them to support market rent across a competitive field of listings.
Should I just take the unit off the market and wait until spring?
Almost never. You are paying for that property every month whether it produces income or not. A shorter term lease at a slightly reduced rate that carries you into the spring market is nearly always better than five or six months of guaranteed vacancy.
How much should I reduce?
Enough to put you in the top half of the comparable units actually available in your neighborhood right now. That amount is different for every property, which is why the exercise of counting your competition matters. Run the tradeoff through the Vacancy Loss Calculator before you decide.
Will a resident really sign a 15 to 18 month lease?
Frequently, yes, and many prefer it. It gives them stability and delays any rent increase conversation. Lead with that benefit rather than explaining your calendar strategy.
Is preleasing legal while someone still lives there?
Yes, provided you follow the entry and notice requirements that apply to your property. Chicago, suburban Cook County, and the collar counties do not all read the same way, so know which framework governs your unit before you schedule the first showing.
What if my unit needs work before it can be shown?
Then get the work scoped and scheduled now rather than after the resident hands back the keys. Every day of turnover work that happens after move out is a day of vacancy in the worst part of the calendar.
Don't Go At This Alone!
Our team handles this exact calendar decision across roughly 1,500 units every single year, and we are making these same three moves right now on behalf of the owners we work with. Competitive pricing analysis, lease terms engineered around the season, and preleasing occupied units before they go vacant are not extras for us. They are the job.
My mission has always been to help investors buy back their time and lower their risk, and nothing lowers risk faster than not being the landlord staring at an empty unit in November.
If you want a real set of eyes on your vacancy, your rent, or your upcoming expirations, we are here.
Related reading:
Author: Mark Ainley | Partner, GC Realty & Development & Co-Host, Straight Up Chicago Investor Podcast
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