What Happened in 2025 When We Overpriced Our Chicagoland Rentals

I hope you have some takeaways from this blog. if you want our team to provide you tenant placement or property management. Click Here
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

Pricing a rental property is more art than science. After 23+ years of leasing over 5,000 investment properties for other investors and myself  across the Chicago metro area, I can tell you that getting the price right is the single most important decision in the leasing process. Not marketing. Not photos. Not timing. Price.

And when we get the price wrong, whether that’s on us or because we couldn’t get on the same page with an investor/client, the data shows the painful delay to getting rent coming in.

I am intrigued by this topic so I analyzed over 350 completed leases from our 2025 portfolio. This was a learning lesson for me and my team and great data for every investor in the Chicago market.

How We Build Our Recommended Rent Range

For every property we manage, we provide a recommended rent range of approximately $200.   When we work with investors we like to set expectations and this range is the worst to best case scenario a property owner can expect.  

A common question we get is, “How long will it take to lease my property” and my answer always starts off with “if we price it right within the range suggested then……”

As a review of how we come up with this range we break it down to the following 5 steps.

Step 1: What Has Actually Leased Recently?

We start by searching what comparable properties have leased in the last 60 days. This gives us a baseline for what tenants are actually paying in the area right now. But we can’t just take those numbers at face value and have to account for the differences with those properties compared to the property we are about to go to market with.  We often get comps from our own portfolio that most investors won't have access to because we leased the property before it ever hit the open market.

Step 2: Adjust for Seasonality

The Chicagoland rental market moves in cycles, and a property leased in September doesn’t tell you what a property will lease for in November. The market slows in the fall and winter. It picks up in the spring and peaks in the summer. If we’re listing a property in February, we can’t take a December lease price as gospel because December is one of the slowest months of the year. We have to make an educated adjustment based on where we are in the seasonal cycle.

Step 3: What’s on the Market Right Now?

This is where most people stop, but for us it’s actually the most important step. Past leases give us a general idea, but what’s actively on the market right now tells us what we’re actually competing against. How many comparable properties are listed? What are they asking? This comes down to supply and demand, and even during the busier months of leasing season, there are times when inventory is just flooded.

Step 4: Account for the Density of the Area

Not all inventory is created equal. Fifteen competing listings in a section of Lakeview or Ukrainian Village is a completely different situation than three competing listings in a far west suburb like Hampshire, where maybe five people move in and out of the area on a monthly basis. The same number of competing properties can mean very different things depending on how much tenant demand exists in that specific market.

This also ties back into seasonality. Fifteen comparable listings in a corner of Lakeview during peak summer leasing season is manageable because tenant demand is high. Fifteen comparable listings in Lakeview in December is a much bigger problem.

Step 5: Where You Need to Be Priced

Here’s a reality that a lot of owners don’t think about. If there are 15 comparable properties on the market, you need to be priced in the lower 50% of that group. Why? Because most renters are only going to look at 5 to 7 properties before making a decision. If they’re sorting by price from low to high, and your property is in the top half of comparable listings, you may never even get a showing. It doesn’t matter how nice your property is if nobody walks through the door.

Getting on the Same Page

One of our biggest goals at GC Realty, especially with new clients, is to get aligned on that range before a property ever hits the market. We want every owner to understand what the worst case to best case scenario looks like for their final rent. When everyone agrees on expectations upfront, the process works. When we’re not on the same page, that’s when things get far more difficult then they need to.

How Our Range Performed in 2025

Here’s how over 350 leased units performed against our recommended range:

We’re proud of that 77% accuracy rate. Nearly half of all units landed in the top quarter of our recommended range, which means our analysis is consistently helping owners capture strong rent. But let’s talk about those 76 properties that leased below the range, because that’s where the real lesson is.

Why We Miss on Price

I want to be upfront about this. When we miss on pricing, it generally comes down to one of two reasons.

We allow an investor/client to start higher against our better judgment. This is the most common scenario. An investor  looks at our recommended range and wants to test a higher price point. We push back when we can, but at the end of the day, it’s the owner’s property and their decision. Sometimes we can’t get them on board with the range, and we go to market above where the data says we should be.

There aren’t strong comparables to work from. Not every property has five identical units that leased nearby in the last 60 days. And not every area has enough active listings to gauge current supply and demand. When we don’t have strong comparable data, either from recent leases or from what’s currently on the market, our range is an educated estimate with more room for error.

A perfect example: we recently looked at a very unique single family home in Elmhurst. Perfect location, good size, quality property. But nothing comparable had leased within half a mile in the last three years. Is it a $4,500 rental or a $5,500 rental? Honestly, we didn’t know. So naturally, you start at the higher end of the range and work your way down, trusting that your marketing is strong enough to surface whatever demand exists. If you’re getting showings and interest at $5,300 to $5,500, great. If there’s no demand at that level, you’ve overshot and you adjust. That’s not a failure. That’s the only way to find the market when the data doesn’t exist.

But regardless of the reason, when we start too high, the result is the same. And the data makes it painfully clear.

What Happens When We Miss

When a property goes to market above where it should be, it doesn’t just miss on price. It misses on time. And time is where the real cost lives.

Properties priced within our range leased in an average of 19 days. Properties that ended up leasing below our range took 47 days. That’s 2.5 times longer.

And here’s the part that really stings: those properties still ended up leasing at or below the price we originally recommended. The extra time on market didn’t result in a higher rent. It resulted in the same rent (or worse) after burning almost a month of extra vacancy.

The Real Cost of a Vacant Property

When people think about the cost of overpricing, they usually think about lost rent. And yes, that’s a big piece of it. But the true cost of a property sitting vacant goes well beyond the rent check you’re not receiving.

Lost Rent

This one is obvious but worth stating clearly. Every day your property sits empty is a day of rent you will never recover. It doesn’t matter what the property eventually leases for. Those vacant days are gone. If your property takes 47 days to lease instead of 19, that’s 28 days of income that evaporated because the listing started in the wrong place. You can’t make that up. It’s just gone.

Check out our Free Vacancy Loss Calculator.  It is always just a math problem!

Utility Payments

While the property is vacant, someone has to keep the lights on, literally. Electric, gas, water. Those bills don’t stop just because there’s no tenant. In the winter, you’re running heat to keep pipes from freezing. In the summer, you may need to run enough climate control to keep the property in showing condition. The longer it sits, the more those utility bills add up, and every dollar is coming out of the owner’s pocket.

Risk of a Vacant Property

A vacant property is an exposed property. Pipes can freeze and burst in winter when nobody is there to notice. A small leak can go undetected for weeks and turn into a major repair. Break ins, vandalism, and squatters are real risks, especially in certain parts of the Chicago metro. The longer a property sits empty, the more risk the owner is carrying. And none of that risk would exist if the property had been priced right and leased on time.

Stress, Frustration, and Your Time

This is the one that doesn’t show up on a spreadsheet but hits the hardest. If you’re the person showing the property, every extra week on the market means more trips to the property, more time carved out of your day, more showings that go nowhere. You’re fielding calls, coordinating schedules, driving to the property, waiting for prospective tenants who may or may not show up, all while knowing the listing is overpriced and the market is telling you so. That wears on you. Multiply that over several weeks and across multiple properties and it’s not just a financial cost. It’s a quality of life cost.

How This Plays Out in the Real World

We see two versions of overpricing play out over and over again.

Scenario A: We Start High, End Up in the Range

We recommend a range of $2,000 to $2,200. Maybe the owner wants to try $2,500. Maybe we didn’t have strong comps and our initial range was off. Either way, the property goes to market above where the market actually is.

It sits. Showings trickle in but nobody bites. After a few weeks, we adjust the price. Eventually it leases at $2,100.

The property landed exactly where the market said it would. The only difference? It took 28 extra days to get there, with all the lost rent, utility costs, risk, and frustration that comes with it.

Scenario B: We Start High, End Up Below the Range

Same starting point, but this time the property sits even longer. The listing goes stale. Prospective tenants scroll past it because it’s been on the market for weeks. The owner gets nervous and agrees to a bigger price cut. It finally leases at $1,795.

Now we’ve lost the vacancy time and ended up below the range. The owner is collecting less rent every single month for the duration of the lease on top of all the vacancy costs they already absorbed. This happened 76 times in our 2025 portfolio.

This Gets Even More Costly in the Fall

Everything I’ve described above gets significantly worse when you overprice a property heading into the fall and winter months.

In the summer, if you’re overpriced, at least you’re overpriced in a market with strong demand. There are plenty of renters actively looking, and even an overpriced listing will get some traffic. You have a cushion. In the fall, that cushion disappears.

Here’s what happens when you overprice going into the slower months. New competing listings come on the market at lower prices because those owners and property managers can see that demand is slowing down. Existing competition starts dropping their prices because they’re worried about sitting vacant through the winter. And the pool of renters actively searching gets smaller by the week.

So now you’re not just overpriced. You’re overpriced in a market that’s actively moving away from you. Every price drop you make is already behind where the market has shifted since you listed. You’re chasing the rental market down, and you’re never catching up.

In the summer, an overpriced listing might sit for a few extra weeks before finding the right tenant. In the fall, that same overpriced listing can sit for months because the market deteriorates around it. By the time you’ve made two or three price adjustments, you’re deep into November or December where demand is at its lowest point of the year. Now you’re either accepting a significantly lower rent than you would have gotten if you’d priced it right in September, or you’re carrying a vacant property through the holidays and into the new year.

This is why we push so hard to get the price right from the start, especially as we head into the fourth quarter. The margin for error gets thinner every week once September hits.

What We’ve Learned (and What We’re Doing About It)

This data isn’t just for owners. We’re using it to get better on our end too.

For properties in areas with limited comparables, we’re building deeper datasets by tracking every lease outcome, price adjustment, and days on market number across our portfolio of 1,400+ properties. The more data points we collect, the more accurate our initial ranges become, even in neighborhoods where traditional comps are thin.

For new client relationships, we’re putting even more emphasis on the pricing conversation before the listing goes live. We want every owner to understand the range, understand what the worst case and best case outcomes look like, and understand the real cost of starting too high. Because the data is clear: the properties that perform best are the ones where the owner and the property manager are aligned on price from day one.

The Bottom Line

I’ve been managing properties in Chicago for over 23 years. I’ve seen every market cycle, every leasing season, and every pricing scenario you can imagine. And the data tells the same story every time.

When we get the price right, properties lease in 19 days. When we miss, they take 47 days and end up at the same rent anyway.

Our recommended range hits the target 77% of the time. Nearly half of all units lease in the top quarter of that range. That’s not luck. That’s 23 years of Chicago market experience backed by data from 1,400+ properties.

The question isn’t whether you might be able to get $200 more per month in rent. The question is whether that possibility is worth the lost rent, the utility bills, the risk to your property, and the stress and wasted time that come with an overpriced listing. In our experience, it isn’t.

Price it right. Lease it fast. That’s how you maximize your return.

Don’t Go At This Alone

This is a lot of information you need to know if you plan to invest in the Chicago market and it may seem overwhelming, but real estate investing in Chicago is a team sport. Who is on your real estate investing team? Do you have a team? GC Realty & Development has a team of resources and we are willing to share all of our 20+ years of experience in both real estate investing and property management in the Chicago market. We will do this whether you hire us or not.

What gets me up in the morning and keeps me going 12+ hours a day of work is the ability to add value to Chicago real estate investors. If we connect you will hear me say our goal as a company is to add value to everyone we come in contact with, and in return we hope one day you will hire us for our Tenant Placement or Property Management Services. You can also refer us to someone you know that needs Tenant Placement or Property Management Services, or I will take a simple 5 Star Google review.

Whether you are a first time investor or a seasoned pro, having the right team behind you makes all the difference. If you want a data backed rent analysis for your Chicago area investment property, reach out to us at gcrealty.com or give us a call. We’ll show you what the market says your property is worth and help you lease it fast.

This is a lot of information you need to know if you plan to invest in the Chicago market and it may seem overwhelming, but real estate investing in Chicago is a team sport. Who is on your real estate investing team? Do you even have a team? GC Realty & Development has a team of resources and we are willing to share all of our 20+ years of experience in both real estate investing and property management in the Chicago market. We will do this whether you hire us or not.

What gets me up in the morning and keeps me going 12+ hours a day is the ability to add value to Chicago real estate investors. If we connect, you will hear me say that our goal as a company is to add value to everyone we come in contact with. In return, we hope one day you will hire us for our Tenant Placement or Property Management Services. You can also refer us to someone you know that needs Tenant Placement or Property Management services, or I will take a simple 5 Star Google review. We love the opportunity when we get all three from the current and aspiring investors we get to help!

Reach out today!

Partner / Co-Host of Straight Up Chicago Investor Podcast

Free Rent analysis

Schedule a call