Same City. Two Worlds.

Current Market Conditions

My dad turned 70 last week.

That’s a big number.

Honestly… it’s a huge number.

He’s the first male we know of to make it that far in our bloodline. On my dad’s side, the men tend to die young. So 70 doesn’t just feel like a birthday,  it feels like a milestone. Like we’re breaking some kind of generational ceiling.

And if you’ve ever met my dad, you know he’s a true Chicago guy.

Big mustache. Looks like he belongs in an SNL skit.
Big dude , 6’4”, 225, and for some reason he only wore tank tops. Like, year round. Didn’t matter if it was 90 degrees or 9 degrees. Tank top season never ended.

I’ve had two completely different relationships with my dad.

One when I was younger.

And one when I was older.

When I was a kid, my dad wasn’t around much. He worked constantly. He ran the company. Work wasn’t just what he did, work was who he was.

I remember waking up and hearing him talking in his sleep about deals.

That sounds crazy. But it was normal in our house.

Even on family trips, he had routines. Set times for calls. Set times to “catch up.” There was always something to handle. Something to manage. Something to solve.

He never sat us down and said “this is how you work hard.”

But he didn’t have to.

We watched it.

And back then, that level of grind wasn’t weird, it was just what you did if you wanted to build something.

Now… he’s also Irish.

Which means he has the stereotypical Irish temper. He could fly off the handle fast. And if you ended up on the wrong side of it, you got the Conan belt.

And let me tell you, you didn’t sit down for a few days after that.

We didn’t really talk much when I was a kid. Not like real conversations. And asking him for something took courage. Because you already knew what was coming:

“We don’t have the money.”
Even if we did.

So it taught me to get creative.

If I wanted something, I didn’t ask like a kid — I pitched it like a business deal. I’d show him a payment plan. How I’d earn it. How I’d pay it back. How it would work.

It was basically my first exposure to negotiation.
And honestly… it was probably my first exposure to sales.

But he wasn’t approachable. Not in that warm, soft way.
He was more like: figure it out.

Then I got older.

And our relationship changed.

I decided to go work for the family company. I wanted to learn from him. I wanted to understand how he did it.

But he’s not the type to teach you step-by-step.

He’s the type to throw you in the deep end and watch if you swim.

So I created my own system.

I’d sit in the office late. Put on a pot of coffee. And just listen. I’d listen to how he talked. How he handled people. How he negotiated. How he stayed calm in chaos.

Sometimes I’d be there until 9 or 10 at night.

Not because I had to.
Because I wanted to absorb it.

Then my mom died.
And he was a broken man.

That was the moment where everything shifted. That’s when I realized I had to step up. And it’s weird how life does that. One day you’re the kid trying to earn approval… and the next day you’re the adult holding the whole thing together.

We still don’t have deep heart-to-heart conversations.

But we talk on a different level now.
We don’t always see eye to eye… but we relate.

It’s like the roles reversed.

He takes more time off.
And I work endless hours.

And it’s funny,  relationships can feel like they’re coming from two different worlds… even when it’s the same two people.

And that’s where the market is today.

We’re a month into the year and we’re still seeing a tale of two cities — inside the same city.

The outskirts are over-performing.
Downtown is underperforming.

High rises and bigger buildings are performing the worst.

It’s wild to see a place in River North that sold for $1.7M in 2019 struggle to get any viewings at $1.4M today.
At the same time, a place that sold for $800K in Lincoln Park in 2021 will sell for $1.2M now.

The price difference is real.

And the appreciation in the outskirts is at levels we’ve never seen.

When a good listing hits the market out there, it’s insanity.

Line around the corner.
20+ offers.
People offering their first born to win the property.

But when a good listing hits the market downtown?

Crickets.
You’re lucky to get a showing.
And unless the property is priced well below what the sellers paid for it, the odds of selling are low.

We thought by now the downtown market would be back.

And it is coming back — slowly.

Inventory is the lowest it’s been in five years.
But even with low inventory, it’s still not a market where everything flies off the shelf.

The light at the end of the tunnel is that entry-level properties are starting to move fast again — especially when they’re priced right.

But the luxury market downtown?
Beyond soft.

There’s a lot of competition and a lot of sellers willing to cut their losses and run.

Meanwhile, buyers are foaming at the mouth for luxury properties in the outskirts.

When one hits… watch out.

You would never see a $2M+ single family in Roscoe Village sell same day.

But now you are.

At the same time, you would never see a $2M single family in the Gold Coast sit for two years.

But it is.

This tale has been going on for five years now, but it still feels like the gap is widening, not shrinking.

And it’s the same city.
Same skyline.
Same lake.
Same streets.

But two totally different realities.

And that’s the tie-in.

Much like how I’ve had two completely different relationships with my dad…
We have two completely different markets.

One market is hungry.
One market is cautious.
One market is emotional and aggressive, fighting for every inch.

The other market is slow, analytical, and cold, waiting, watching, refusing to overpay.

And here’s the truth:

The market doesn’t care what you paid.

It doesn’t care what your neighbor got in 2021.
It doesn’t care what you “need” to walk away with.
It only cares what buyers are willing to pay today.

My dad never sat me down and said “adapt.”

But he lived it.

He built a company in an era where you didn’t get participation trophies, you either figured it out or you got left behind.

And that’s exactly what Chicago real estate is doing right now.

Because what worked downtown doesn’t work in the neighborhoods.

What worked in 2019 doesn’t work in 2026.

And what worked for sellers the last few years?

That era is over.

Same city. Two worlds.

And just like life forces you to grow up… the market has a way of pulling you back to reality.

Demand grew again this week. That’s a great sign, and I expect demand to keep surging as we head deeper into spring.

Inventory grew again this week, and we’re finally in a nice rhythm of new listings consistently hitting the market.

Rates were basically on par with last week, maybe down a tad.

Contract surged this week. Buyers are writing

With that being said, multiple bids were up too.

Desperate buyers are showing up again. Anyone with a lease ending in April is feeling the pressure, and they’re writing aggressive offers to lock in a home before they get left behind.

We should see more listings hit after the Super Bowl. Expect fewer listings this upcoming week, but a lot more the following week.

What it takes to win. In the outskirts, the trend is simple. Buyers are doing whatever it takes. No financing, as-is, $100K+ over ask. Some of these offer situations are getting crazy, and buyers are pushing all the chips in. This is going to be the trend all spring.

Single Family Homes 
We’re still seeing buyers line up for any new home that hits the market in an entry-level price point. Inventory remains extremely limited and demand is very high. I expect this trend to continue through Spring Break. Mid-tier and luxury price points are also starting to heat up. Keep an eye on the period right after the Super Bowl. Historically, we tend to see a wave of single-family listings hit the market then, and it will be interesting to see if that happens again this year. For now, this remains a strong seller’s market.

Lincoln Park, Lakeview, North Center, Roscoe Village
What do you get when there’s almost no inventory and buyers who need to buy before their lease expires? Crazy bids. Entry-level properties are getting the most offers right now because demand is the highest in that price point. We’ve also seen almost no duplex-downs or townhouses hit the market yet. Similar to single-family homes, keep an eye on the period right after the Super Bowl. Historically, that’s when we tend to see more of those come on. Inventory is the biggest issue right now, and because of it, this remains a huge seller’s market.

West Town, Wicker Park, Bucktown, Logan Square, Avondale
Same as above.

West Loop
I’m starting to see a little bounce back again. High-end luxury units in the top luxury buildings are seeing a noticeable uptick. Entry-level listings are also starting to move quickly. The mid-tier has been hit the hardest, but we’re finally seeing a small amount of momentum return. We said to keep an eye on this market this year, and it does appear to be slowly turning. For now, I’d call it balanced with a slight edge to buyers, but I expect it to feel more balanced over the next few weeks.

Old Town
Old Town is still very hot. There isn’t enough supply to keep up with demand. We’re continuing to see smaller buildings outperform the larger buildings, but overall the market remains very strong. This is a major seller’s market.

South Loop
The South Loop has been down overall, but we’re seeing a nice bump in activity in the entry-level buildings. Units need to check the key boxes, low HOA, in-unit washer and dryer, and the right price, but we are seeing a good amount of contracts happening there. We’re even seeing a slight uptick in showings on the high-end luxury side, but those listings still need to be priced below market to generate real activity. The mid-tier is still struggling, though we’re starting to see a little more action there as well. Overall, South Loop remains a buyer’s market.

New East Side & The Loop
This is still the worst area in Chicago right now. Inventory is the highest here, and demand is the lowest. The upside is that demand is starting to creep up in the entry-level market. We’re also seeing some top-tier luxury units move, but they typically need to be priced well below what the seller paid, or what the unit is truly worth, to generate a sale. This is definitely one to watch this spring to see if demand continues to improve. One buyer group we need to see more of is empty nesters and in-towners. If that segment returns, it could shift momentum. For now, it remains a buyer’s market.

River North, Streeterville, Gold Coast
We saw some life here for once. The entry-level and mid-tier markets are finally getting some action, but it has to be priced well. Anything that reaches sits. The listings that are priced correctly are selling, and selling fairly quickly. This is the first time we’ve really seen that. The biggest struggle is still the luxury market. We’re seeing a little bit of activity, but there’s a lot of inventory at the high end. The only units moving are the ones priced well below market value or the ones that show extremely well with over-the-top upgrades. This is a market to watch closely as we head deeper into spring to see if demand continues to build. For now, it remains a buyer’s market.

The Big Picture:

• Outskirts: It remains a seller’s market across all categories, 

• Downtown Core: Is a buyer’s market.