- Oprah Winfrey
- Kanye West
- Barack Obama
- Jennifer Hudson
- Ben Savage
- John Cusack
- Jenny McCarthy
- Kristin Cavallari
- Gillian Anderson
- Vince Vaughn
Oprah Winfrey is the most famous celebrity that lives in Chicago. But, of course, it’s just one of many cities she spends her time in. To a point, it almost feels like Oprah has a property in every city imaginable. The billionairess has been the Queen of All Media for a reason. That reason? She’s famous and knows how to manage her money well.
Along with a gorgeous home in Florida, one in Los Angeles, and a place in New York State, Winfrey owns a luxury penthouse in Chicago. According to rumors, she’s quite secretive about the location of her penthouse. One could only imagine what kinds of epic decorations she has there.
With that said, her Chicago home is more of a pied a terre than a permanent home. Even so, we’re sure the city is happy to have her.
Yes, it’s true. Kanye was originally from Chicago and spent eight years of his childhood with his mom, Donda, in the city. His original childhood home, 7815 S. Shore Drive, has become a legendary hip-hop location because of how frequently it’s been referenced in his music.
For a while, Ye walked away from his time in South Shore. However, he bought his childhood home back in 2020. So, it’s safe to say that he’s a huge fan of the city and the impression it’s left on him.
You know that a city has to be amazing to be able to house one of the best presidents of the modern era, right? Barack Obama was America’s 44th president, and although he’s purchased numerous homes since his two terms ended, he and Michelle still own their Chicago house.
Chicago has been a favorite location of the Obamas for ages. So it makes sense that they would want to kick back in the lap of luxury here after they’ve done so much for a country that’s in such turmoil.
The Boy Meets World star who won over the hearts of a generation might still do a decent amount of work in Hollywood, but he still has a reputation for being based out of Chicago. He used to own a 5-bed, 5.5-bath home in the Glencoe region. Rumors say he still has a place here.
However, Savage has been very vocal about getting into California politics. He’s been mostly in LA since he wants to get political, which is totally cool. But he’s still a Chi-Town guy.
If you are a fan of 80s movies, you might remember John Cusack of 16 Candles. He’s been active in the movie scene since then, and the truth is, he shows no sign of stopping anytime soon. However, that doesn’t mean he spends all his time in LA.
Cusack is one of many celebrities who is originally from Chicago. He grew up in the city and reportedly still has a home there, primarily because he’s a diehard Chicago Cubs fan. After all, he’s got to be close to watch those games, right?
Ladies might recognize the chatty blonde bombshell as one of the hosts of The View. It’s true. She has a comfortable life doing shows in New York City, but don’t be fooled. While she may work in the Big Apple, her heart’s still in Chicago.
According to multiple sources, Jenny goes back to Chicago’s outskirts whenever she is not taping stuff in her NYC-based talk show. She can’t get enough of that delicious Chicago pizza, much to New Yorkers’ chagrin!
American Idol breakout star Jennifer Hudson originally hailed from Chicago and made a point of letting people know. The beautiful songbird has since found fame and fortune doing singing stints throughout the United States.
Jennifer Hudson no longer sticks to Chicago alone, but she still retains some property in the area. When she’s not on tour, she keeps busy with multiple visits to her hometown. According to Hudson, it helps ground her as she navigates Hollywood.
Former “It” girl Kristin Cavallari became every teenager’s envy from her time spent on the hit TV show, The Hills. While she may no longer be plastered on every teen magazine on stands, Cavallari is still living a very enviable life.
According to our research, she is happily married to Jay Cutler of the Chicago Bears. Considering that he needs to play in Chi-Town, it is no surprise that her happily ever after is in the middle of Chicago.
Gillian Anderson first won over hearts with her breakout role in X-Files, but don’t be fooled. She was working and living in Chicago for years before she got discovered and launched her career as a famous detective.
She had to spend time away from her hometown for the longest time. Then, in 2013, she was offered a role in a long-term show that allowed her to move back to Chicago. She’s been a local resident ever since and shows no sign of moving to another town anytime soon. That’s Chicago for ya!
Another famous Chicagoan is Vince Vaughn. A true sportsman to the core, it comes as no surprise to any of his fans that Vince Vaughn truly loves Chicago. He’s repped the city for so long that it only makes sense. He still owns property in the city and visits from time to time.