The 20 Most “On-the-Up” Housing Markets Right Now (and Where Chicago Lands)

If the 2025 housing market were a treadmill, a handful of metros just slammed the incline button—and didn’t hang on to the rails like the rest of us. Here’s a copy-paste-ready roundup of the 20 markets trending up as of October 3, 2025, plus a Chicago reality check you can brag about at open houses.

How we picked the climbers (so you don’t have to)

I combined two gold-standard lenses:

• Redfin’s latest monthly metro snapshots (Aug 2025) for fast reads on where median sale prices are jumping.

• S&P CoreLogic Case-Shiller (July 2025) for an index-based view of the biggest metros (apples-to-apples over time).

Together? You get the smaller/mid-size markets that are ripping, and the heavyweight cities proving it’s not just a one-hit wonder.

Top 20 “inclining” markets (as of today)

Fast movers on median sale price (Redfin — Aug 2025)Birmingham (AL) • Rockford (IL) • Washington, DC • Alexandria (VA) • Des Moines (IA) • Little Rock (AR) • Honolulu (HI) • Pittsburgh (PA) • St. Louis (MO) • Lakewood (CO)

Translation: if these markets were stairmasters, they’d be the ones the trainers warn you about.

Leaders among the largest metros (Case-Shiller — Jul 2025)New York (NY) • Chicago (IL) • Cleveland (OH) • Boston (MA) • Detroit (MI) • Charlotte (NC) • Atlanta (GA) • Minneapolis (MN) • Denver (CO) • Dallas (TX)

Translation: the heavyweights aren’t just maintaining—they’re climbing with good form.

Where does Chicago land?

Right near the top. Among the 20 largest metros tracked by Case-Shiller, Chicago is the #2 gainer year-over-year, just behind New York. In other words: we’re not just “steady Midwest” anymore—we’re “speedy Midwest.”

Use this in your listing presentation:

• “Chicago’s one of the nation’s top big-city climbers right now.”

• “Buyers, don’t sleep: pricing smart beats chasing later.”

• “Sellers, leverage the momentum—but watch comps and days-on-market so you don’t end up in ‘wish-price’ limbo.”

What this means for buyers & sellers (no fluff, just field notes)

1) The Midwest is flexing.Rockford, St. Louis, Cleveland, Chicago—the center of the map is carrying the gains like it’s squat day.

2) National trend = positive but chill.U.S. prices are up modestly year-over-year. It’s not 2021 turbo mode, but it’s not a slide either. Picking the right micro-market matters more than ever.

3) Price cuts exist—just not in the winners above.Plenty of metros saw a record share of sellers cutting list price. Moral: price it right and you won’t have to chase the market down the hill.

The fun (but actually useful) cheat sheet

• If you’re relocating: Put the fast-mover list on your radar (Birmingham to Honolulu). Momentum + affordability can be a sweet combo, especially for first-time buyers or investors.

• If you’re upsizing in Chicago: You’re surfing a tailwind. Use a data-tight CMA and lean on concessions instead of over-listing.

• If you’re selling in a price-cut city: Don’t panic—reposition. Improve photos, tweak terms, time your reductions, and target the move-ready crowd.

One-liner you can steal for your newsletter

“Chicago is one of the strongest big-city climbers in 2025—proof that the Midwest isn’t just steady; it’s sprinting.”

Sources

(Everything above reflects the latest available releases as of October 3, 2025.)

• Redfin — U.S. Housing Market (Aug 2025): national YoY, price-drop share, and metro-level views. Redfin

• Redfin — Data Center (metro downloads & charts). Redfin

• Redfin News — Price drops at a record rate (Aug 2025): which metros saw the most cuts. Redfin

• S&P Dow Jones Indices — S&P CoreLogic Case-Shiller (July 2025): official release (PDF). S&P Global

• Calculated Risk — summary of the same Case-Shiller release (NYC #1, Chicago #2, Cleveland #3). Calculated Risk