Zillow, Redfin, and the Shrinking Rental Market: What It Means for Chicago Right Now

By Sean Flynt, Pioneer Realty Group

A new antitrust lawsuit from the FTC is shaking up the national rental housing conversation—but if you’ve been trying to rent or advertise an apartment in Chicago, the effects aren’t some future threat. They’re already here.

On September 30, 2025, the Federal Trade Commission (FTC) sued Zillow and Redfin over what it alleges is an illegal agreement to eliminate competition in multifamily rental advertising. According to the complaint, Zillow paid Redfin $100 million to stop competing and instead act as a syndicator—essentially, a billboard for Zillow’s own listings.

While the legal outcome is yet to be decided, the consequences for renters, landlords, and property managers in Chicago are very real and already unfolding. I want to walk you through what’s happening, what it means for our market, and why now—more than ever—it’s critical to work with ethical, independent housing professionals.

🔒 Fewer Choices for Renters

Millions of renters rely on internet listing services (ILSs) to search for housing. In fact, these platforms have replaced yard signs and word of mouth as the primary way to find a home. But the FTC alleges that Zillow’s deal with Redfin wipes out meaningful competition in this space.

Here’s what that means on the ground:

• The same listings now appear on fewer platforms.
• Redfin no longer allows multifamily properties to advertise independently.
• Zillow becomes the sole gatekeeper of what renters see on multiple sites.

For the renter, this translates into less visibility, less diversity in options, and ultimately, higher prices.

When competition disappears, platforms lose incentive to make listings better, cheaper, or more accessible. Instead, they can control the flow of information—and that control comes at a cost.

💸 Advertising Prices Have Skyrocketed in Chicago

Let’s talk about what property managers and landlords are seeing firsthand:

• Just a few years ago, you could list a unit in Chicago for free—or at most, for a modest fee on multiple sites.
• Today, many platforms have introduced steep tiered pricing, monthly recurring ad costs, and “boost” packages just to get your unit seen.
• Properties that aren’t “promoted” are buried in the listings, invisible unless someone digs deep or filters by price.

And this isn’t just about extra fees—it’s about the concentration of control. The same dominant players now own or syndicate across multiple listing channels, which means that property managers and owners have no real choice if they want visibility.

We've spoken with landlords across Chicago—many of whom manage just a few units. They tell us it's now prohibitively expensive to advertise. In some cases, they're spending hundreds of dollars just to get a listing live, with no guarantee of leads. That's a huge burden, especially for smaller owners who serve working-class neighborhoods.

🔁 What Happens When Listings Become a Monopoly?

Let’s be clear: this isn’t just a nuisance for landlords. This changes the economics of the entire rental market.

When it costs more to advertise a unit:

• Landlords often pass that cost along to renters.
• Smaller landlords may drop out of online advertising, making their units effectively invisible.
• Renters are shown a narrower slice of the market, which reduces their negotiating power.
• Larger management companies and institutional landlords dominate the visibility—and often command higher prices with fewer questions asked.

What we’re seeing in Chicago is a dangerous loop:

Fewer listings → Less visibility → Higher rents → Higher ad costs → Fewer listings.

This is not a healthy rental ecosystem.

🏙️ What We're Seeing in Real Time at PRG

Here at Pioneer Realty Group, we’ve already had to adjust our strategy to ensure our clients and tenants still have access to a full market picture.

We’ve seen:

• Free or low-cost listing sites disappear or become paywalled.
• Duplicate listings show up across different platforms, even when they lead back to the same companies.
• A rise in renters only seeing a fraction of what’s actually available in neighborhoods like Logan Square, Uptown, or Avondale.
• Inquiries from renters who say they feel "trapped" in what the algorithm is showing them.

And perhaps most critically: we've seen landlords priced out of the ability to compete—which directly affects the choices renters have.

👎 Why This Hurts Chicago's Rental Market More Than Most

Chicago is a neighborhood city—diverse, localized, and made up of thousands of small landlords and mid-sized property managers. We're not dominated by institutional investors or national-scale landlords in the way some cities are.

That means this kind of consolidation is particularly harmful here.

If you're a:

• Small landlord trying to rent out your 2-flat unit in Lincoln Square
• Mid-sized manager with 20 units in Albany Park
• Renter looking for a deal in Pilsen or Humboldt Park

...you’re getting squeezed. Not just by market forces, but by platform politics. Visibility is no longer a meritocracy. It's a bidding war.

🙌 What Renters and Landlords Can Do About It

Here’s the good news: we’re not powerless.

🧑‍💼 For Renters:

• Use multiple sources. Go beyond the top listing sites. Search local brokerages, neighborhood Facebook groups, Reddit threads, and Craigslist.
• Ask about unlisted inventory. Some of the best deals are in the hands of local agents who know owners personally—and don’t list through the big platforms.
• Work with community-based brokerages. You'll get better service, faster responses, and a wider view of the market.

🏠 For Landlords:

• Stop relying on one platform. Diversify your strategy with local brokerages, direct renter outreach, and social channels.
• Track what you’re spending vs. what you’re getting. If you're paying $200 a month and not getting leads, it's time to rethink.
• Partner with firms like ours. We know how to get visibility without overpaying for ads. We hustle, we network, and we invest in systems that don’t rely on corporate monopolies.

💬 Why Work with Pioneer Realty Group?

At PRG, we’ve always believed in transparency, fairness, and community-based housing solutions. That’s never been more important than it is today.

• We don’t force landlords into overpriced marketing funnels.
• We maximize listing exposure across both traditional and modern channels—at fair prices.
• We work directly with local renters, helping them find homes that aren’t buried behind paywalls.
• We’re independent, which means we answer to you—not to some shareholder strategy that values market share over service.

We see what’s happening in the listing world. And we’re choosing to take a different path.

📣 Final Word

The FTC lawsuit against Zillow and Redfin should be a wake-up call for anyone involved in renting property—especially in a city like Chicago. When fewer companies control more of the market, everyone pays—renters, landlords, and communities alike.

But it’s not too late to shift course. Use platforms that promote openness. Work with people who value fairness. And most importantly: demand better.

We’ll keep doing our part. If you need help finding a place to live or renting out a property—without feeding the machine—we’re here.

👉 Visit chicagoprg.com
📞 Call us to talk about your next rental strategy
📬 Or drop us a message and let’s build something better together.