Celebrities with Chicagoland Homes in 2025

Chicago is a hotspot for not only filming famous television shows like The Bear and Shameless, but also for extravagant celebrity homes. As the country’s 3rd largest metropolitan area, Chicago has long been a magnet for celebrities who choose to make the Windy City their home. Known for its rich cultural history, world-class architecture, and resilient spirit, the city offers an attractive blend of high-class living and vibrancy. Some stars reside here full-time, while others maintain pied-à-terre-style residences to stay connected to the city that helped shape their careers. 

Below is a detailed look at some of the biggest actors, musicians, and media icons who currently live in Chicago, either part-time or full-time, all with their own unique ties to different neighborhoods.

Media & Public Figures

Oprah Winfrey – Media Mogul (Part-Time Resident)

Oprah maintains homes in multiple cities, but she still keeps a luxury penthouse in Chicago as a personal retreat. While the exact location is private, like many big-name celebrities, her presence in the city where The Oprah Winfrey Show was produced remains symbolic. Oprah’s deep legacy in Chicago media makes her part-time presence feel permanent to locals.

• Neighborhood: Undisclosed luxury penthouse
• Fun Fact: Chicago was her career-launching city

Barack Obama – 44th U.S. President (Part-Time Resident)

Barack and Michelle Obama still own their iconic red-brick Georgian Revival mansion in Chicago’s Kenwood neighborhood on the city’s South Side. This six-bedroom home was their residence before moving to the White House while President Obama was still an Illinois Senator. While they primarily live in Washington, D.C., and Martha’s Vineyard now, the house remains under Secret Service protection and a local landmark.

• Neighborhood: Kenwood
• Notable Feature: Popular stop for tourists and political admirers

Film & TV Personalities

George Lucas – Filmmaker, Star Wars Creator (Part-Time Resident)

George Lucas, the mind genius behind Star Wars, has strong Chicago ties through his wife, Mellody Hobson, a high-profile Chicago businesswoman. Together, they own a sprawling, 9-bedroom, 10-bathroom duplex in the ultra-luxurious Park Tower on North Michigan Avenue. Estimated at $35 million, the home was created by combining two units. Though Lucas splits time between California, locals have reported sightings of him strolling the Mag Mile or enjoying local parks, taking photos.

• Neighborhood: Park Tower, North Michigan Avenue
• Notable Purchase: Combined two condos for ultimate luxury living

Michael Shannon – Actor (Full-Time Resident)

Known for his intense screen presence in films and shows like Boardwalk Empire and Superman, Michael Shannon lives full-time in the artistic Logan Square neighborhood. His vintage-style home, purchased for about $1.34 million, reflects his appreciation for history and character. Shannon is often involved in local theater productions and community events, solidifying his image as a dedicated Chicagoan.

• Neighborhood: Logan Square
• Fun Fact: Balances Hollywood roles with Chicago stage work

Joan Cusack – Actress (Full-Time Resident)

A Chicago native, Joan Cusack has remained loyal to her roots, living in a restored historic mansion in the prestigious Gold Coast neighborhood. Her $4.66 million home, complete with five bedrooms and seven bathrooms, blends elegance with classic architecture. Cusack chose to raise her children in the city, and her presence adds high-class Hollywood prestige to the area.

• Neighborhood: Gold Coast
• Known For: Working Girl, In & Out, and keeping it real in Chicago

John Cusack – Actor (Part-Time Resident)

Joan’s younger brother, John Cusack, remains closely tied to his hometown. Though he travels often for work, he maintains a condominium on the 45th floor of a North Side high-rise, purchased in 2005 for around $2.9 million. Known for his love of the Cubs, Cusack frequently attends games at Wrigley Field (which he never misses when he’s in town) and engages with the city on a grassroots level.

• Neighborhood: North Side area
• Known For: Being John Malkovich, Say Anything, and High Fidelity

Jenny McCarthy / Donnie Wahlberg – TV Personalities, Actor/Actress (Full-Time Resident)

Jenny McCarthy and her husband, actor Donnie Wahlberg, call the Chicago suburb of St. Charles home. After growing up in nearby Evergreen Park, McCarthy decided to stay close to her roots. The couple has transformed their home into a family-friendly space while she commutes to New York for work. If you’re looking for a chance to meet Donnie, they have chosen St. Charles to open up the only Wahlburgers location in Chicagoland.

• Neighborhood: St. Charles
• Known For (Jenny): Singled Out, The View, and hometown pride
• Known For (Donnie): Band of Brothers, Saw II, and Wahlburgers

Music & Entertainment Stars

Kanye West – Rapper, Producer (Part-Time Resident)

In 2020, Kanye West repurchased his childhood home in the South Shore neighborhood — a modest house that features prominently in his music. Although he resides primarily in California and Wyoming, this act of reconnection was a powerful nod to his roots.  The Home nearly faced demolition before being rescued – restoration permits were obtained to bring the property back to life after it had fallen into disrepair.

• Neighborhood: South Shore
• Known For: Graduation, College Dropout, and Yeezy Brand

Jennifer Hudson – Singer, Actress (Part-Time Resident)

The American Idol alumni and EGOT winner owns a luxurious 12,000 sq ft mansion in Burr Ridge, a suburb roughly 17 miles from downtown Chicago, purchased in 2011 for $3 million. Even though the six-bedroom home is outside of Chicago, the location allows Jennifer to take advantage of offers peace and privacy while still having close access to the city when needed. When she’s not filming in L.A., Hudson has publicly said that returning to Chicago keeps her grounded. 

• Neighborhood: Burr Ridge
• Known For: Dreamgirls, Respect, and her talk show

Chance the Rapper – Rapper, Philanthropist (Full-Time Resident)

Chancellor “Chance” Bennett is one of the most beloved modern celebrities in Chicago. In 2021, he and his wife bought a $2.3 million mansion in Bannockburn, complete with a home studio and 3.7 acres of land. Unlike many stars who flee the Midwest, Chance is actively engaged in the community and local charities, and is often spotted attending community events.

• Neighborhood: Bannockburn
• Notable Project: Continued investment in Chicago youth programs

CM Punk (Phil Brooks) – Professional Wrestler & Actor (Full-Time Resident)

Former WWE Champion CM Punk lives in a modern $2.15 million home in Bucktown. His contemporary-style house features four bedrooms and five bathrooms, fitting his edgy wrestling persona. CM Punk is often seen working out in local gyms or attending Blackhawks games, showing that his connection to Chicago is anything but performative.

• Neighborhood: Bucktown
• Known For: Staying loyal to the city while most wrestlers relocate

Sports Stars & Other Personalities

Jonathan Toews – Hockey Player (Full-Time Resident)

Though his Blackhawks tenure ended in 2023, longtime team captain Jonathan Toews has remained in Chicago. In 2014, he upgraded to a 6,400 sq ft mansion in Lincoln Park, previously owned by a tech executive. Known for his leadership both on and off the ice, Toews remains engaged in the local community and enjoys the city’s vibrant dining and lakefront life.

• Neighborhood: Lincoln Park
• Home Value: ~$3.5 million

Tyler “Ninja” Blevins – Video Game Streamer (Full-Time Resident)

One of the most recognizable names in esports and gaming, popular streamer Ninja lives in the Chicago area, staying true to his suburban roots. Despite the tech world’s pull to the coasts, Ninja has stayed local, even hosting major streaming events in Chicago, something that is found more in cities like L.A. and NYC.

• Neighborhood: Chicago (exact location private)
• Known For: Becoming the face of Fortnite and Twitch

Angel Reese – Professional Basketball Player (Full-Time Resident)

A standout forward for the Chicago Sky, Angel Reese lives in a luxury high-rise in the South Loop. She drew attention online when she joked about her $8,000 monthly rent, which is offset by her lucrative endorsement deals. Despite her fast rise, she has embraced Chicago life and can often be seen around town.

• Neighborhood: South Loop
• Known For: WNBA stardom, viral social media presence

Mike Ditka – Former NFL Player & Chicago Bears Coach (Full-Time Resident)

Legendary Chicago Bears coach Mike “Da Bears” Ditka and his wife recently returned to Chicago after a stint in Florida. Rumors spread that Ditka was going to enter hospice care in Florida, but as of now, they reside in the same apartment complex where they lived before moving south. Ditka has always referred to Chicago as his “real home,” and fans are thrilled to have him back.

• Neighborhood: Downtown Chicago
• Notable Return: Rejoined the community he helped define

Simone Biles – Olympic Gymnast (Part-Time Resident)

Simone Biles, the most decorated gymnast in history, has been living in Chicago during the NFL season to support her husband, Jonathan Owens, who plays for the Chicago Bears. Although their long-term home is in Houston, she’s shared her experiences enjoying Chicago and supporting the team from the sidelines.

• Neighborhood: Temporary stay during NFL season
• Fun Fact: Regularly posts Chicago adventures on social media

FAQs About Celebrities Living in Chicago

Who is the most famous celebrity living in Chicago?
Oprah Winfrey and former president Barack Obama top the list, even as part-time residents.

Where do celebrities live in Chicago?
Popular neighborhoods include Gold Coast, Bucktown, Kenwood, South Loop, and suburbs like Burr Ridge and Bannockburn.

Can I visit celebrity homes in Chicago?
Unfortunately, most are private locations, but public sightings happen frequently around events and neighborhood hotspots, especially at Chicago-centric events like Cubs games and neighborhood festivals.

Do celebrities in Chicago engage with the community?
Many celebrities, like Chance the Rapper and Michael Shannon, are involved in local arts, sports, and charity.

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