Why Are Some Downtown Chicago Homes Selling at 1990s Prices?

Not long ago, I saw another agent mention that certain downtown Chicago condos are selling at prices not seen since the 1990s. That caught my attention. After all, most of the Chicago market has been climbing for years—so why would part of downtown be going backwards?

I decided to take a closer look at the numbers and trends to see what’s really going on.

A Market Unlike the Rest of Chicago

While much of the Chicagoland real estate market has thrived in the past decade, downtown condos have lagged behind—and in many cases, even declined in value.

Between 2014 and 2023, the median home price downtown fell 17%, dropping from about $326,000 to $284,000. Over the very same time frame, the rest of the city saw prices rise about 40%.

That’s an astonishing contrast: while neighborhoods across Chicago were appreciating, the downtown core was losing ground.

Why the Downtown Drop?

Several factors combined to create a challenging environment for downtown sellers:

Crime & Safety Concerns – Some buyers hesitated to invest downtown due to perceptions of safety.
High Taxes & Assessments – Many condos carry steep HOA fees and property taxes that push monthly costs higher.
Work-from-Home Lifestyle – The pandemic showed people they didn’t need to live near the office. Many chose larger homes in the suburbs.
Oversupply of High-Rises – A surge of luxury buildings increased inventory while buyer demand shifted elsewhere.

All of this meant that while single-family homes and suburban properties surged in value, downtown condos struggled to keep pace.

What About 2025? Signs of Stabilization

The story doesn’t stop in 2023. More recent data shows that downtown Chicago may finally be turning a corner.

Redfin (July 2025): Median downtown home sale price is $425,000, up 1.2% year-over-year.
Realtor.com (July 2025): Median listing price is $485,000, with homes selling just 1.7% below asking.

So while it’s true that some individual buildings are still selling at 1990s pricing, the broader trend suggests stabilization and even modest recovery downtown.

What About the Rest of Chicago and the Suburbs?

It’s important not to confuse downtown’s unique challenges with the wider market.

Citywide: Home prices across Chicago rose about 40% between 2014 and 2023, showing broad strength outside the core.
Suburbs: Demand in suburban areas has remained strong, driven by families seeking more space, schools, and quieter communities.
Competition: Many suburban homes are still selling quickly, sometimes with multiple offers—very different from the slower pace of many downtown condos.

In other words: real estate is hyper-local. Just because one neighborhood struggles doesn’t mean the whole region is.

Final Thoughts

Downtown Chicago has had a tough decade, with some condos trading at values not seen in decades. But new 2025 data shows that the broader downtown market may finally be bottoming out and stabilizing. Meanwhile, the rest of Chicago and its surrounding suburbs continue to see steady growth.

For buyers, this could mean opportunity downtown—especially if you believe in a long-term rebound. For sellers, it means you need a smart pricing and marketing strategy to stand out.

About Me

I’m Frank Campobasso, a licensed real estate professional with over 20 years of experience helping buyers and sellers throughout Chicago and the suburbs. I specialize in pricing, preparing, and marketing homes to sell quickly and for top dollar. I’ve also been featured in real estate magazines, newspaper articles, and radio shows for my expertise.

Whether you’re considering selling a downtown condo, buying in the suburbs, or even relocating out of state, I’d love to guide you through the process.

📞 773-425-6265
🏢 Century 21 Circle
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