Biggest Celebrity Real Estate Moves in Chicago This Year (2025): You Won’t Believe Number 3!

From million-dollar mansions to TikTok-famous lofts, here’s who’s buying, selling, and “just browsing” like the rest of us—except with, you know, a few extra zeroes in the bank account.

Where Are Chicago’s Stars Living Now?

Chicago’s A-list has been making real estate moves in 2025—some splashier than a Cubs home run in July! Ready to peek behind the velvet rope? Don’t worry, we promise not to tell your landlord you’re dreaming big.

1. Chance the Rapper’s Gold Coast Penthouse: Alexa, Play “Blessings”

When your career’s on fire, you need a pad to match. Chance the Rapper just dropped $4.2 million on a Gold Coast penthouse that’s so high up, he’s officially above the cloud line (sorry, Willis Tower).Features: Rooftop that’s better than most rooftop bars, a recording studio bigger than my first apartment, and smart home tech that probably raps back.Why here? Chance says he wanted to “stay close to Chicago roots”—but we think the heated toilet seats sealed the deal.

2. Jonathan Toews Sells His Lincoln Park Mansion: Hockey Stick Not Included

Blackhawks legend Jonathan Toews has traded his Lincoln Park mansion for $5.5 million. It’s got a home gym, an indoor sports court, and enough garage space for, like, six Zambonis. Where’s he off to? Rumor has it he’s headed north—like, “North Shore, please don’t make me shovel my own driveway” north.

3. Jennifer Hudson’s Naperville Estate: All the Single Ladies (and Olympic Pools)

Jennifer Hudson is showing off her pipes and her pool, dropping $3.8 million on a Naperville estate with a movie theater, Olympic-sized swimming pool, and a closet bigger than your local Zara.Bonus trivia: This house allegedly once belonged to a Chicago Bulls player. Is there a secret basketball court hidden behind the wine cellar? Only J-Hud knows.

4. TikTok Food Star “@ChiCityEats” Buys River North Loft: Now Accepting Brunch Invites

Why just watch food videos when you can live in one? Chicago’s own TikTok sensation @ChiCityEats scooped up a River North loft with exposed brick, soaring ceilings, and a fridge that finally fits all those viral leftovers.The real headline? Her home tour video already has 3 million views—her plant collection gets more likes than my entire real estate Instagram.

Other Celebrity Moves Lighting Up the Market

• A former Cubs pitcher buys a Lakeview pad—close to Wrigley and, more importantly, every taco place on Clark.

• A famous radio host lists a vintage Uptown condo, with a soundproof room for belting out karaoke (or hiding from the news).

• Top chef grabs a Lake Michigan retreat: will there be a reality TV show called “Baked on the Beach”? We can only hope.

Do Celebrity Moves Raise Home Prices?

Yes—and they also raise your standards. Suddenly that two-bedroom looks a little small, doesn’t it? Fun fact: When stars buy in your neighborhood, everyone pretends they don’t notice, but Zillow searches triple overnight.

Wanna See Inside These Celebrity Cribs?

You don’t need a million-dollar paycheck (or a Grammy) to find your own dream home.Contact The Rosenberg Group for a tour—heated toilet seats not included, but we’ll throw in plenty of fun stories and a killer home search.

Share this post if you’d crash Chance’s rooftop party, or tag a friend who thinks their fridge is influencer-level. #ChicagoCelebHomes #NotMyHouseButICanDream