Oprah Winfrey Returns to Her Former Hometown of Chicago as She Makes Rare Appearance With Partner Stedman Graham

TV mogul Oprah Winfrey has gone back to where her media career started—returning to her former hometown of Chicago, where she enjoyed a sweet reunion with her former colleagues on "The Oprah Winfrey Show" weeks before the 40th anniversary of its premiere episode.

The 72-year-old media personality was joined for the emotional occasion by her longtime partner, Stedman Graham, marking the couple's first public appearance in nearly seven years.

Images shared on LinkedIn by one of Winfrey's former producers, Jill Van Lokeren, show the happy couple celebrating the milestone occasion with a large platter of fried chicken at the event, which was held at Chicago's Navy Pier.

The couple also posed for a snap alongside chef Art Smith at the star-studded event.

“15 year reunion for 'The Oprah Winfrey Show.' The best segment 1 surprise guest showed up. A night of all love and pure joy. Forever grateful @oprah + @thechefartsmith hosting at his fabulous @reunionnavypier was an added treat," Van Lokeren wrote.

While the event was held in honor of Winfrey's former show, this year also marks a very significant milestone in her relationship with Stedman, whom she began dating in 1986, the same year that her show premiered.

Winfrey opted for a chic and casual look, sporting a matching cream pinstripe blazer and pants. Graham donned a black suit and white shirt.

“I cannot even believe that as of next month, Sept. 8, it will be 40 years since we first launched 'The Oprah Winfrey Show.' Thank you for being the greatest team ever,” Winfrey said in a speech, which was shared on Instagram.

The couple, who have been together for four decades, have chosen to keep their relationship out of the limelight. They were last seen in public together in 2019.

According to multiple reports, the duo met at a charity event and initially started out as friends, before their relationship blossomed into a romance. While they did get engaged in 1992, they called it off just one year later, with Winfrey later revealing that she had no interest in being married, despite remaining committed to her partner.

Today, the couple reside primarily in Winfrey's extraordinary Montecito, CA, mansion, which is known as The Promised Land. However, the earliest years of their romance remain firmly planted in Chicago, where the TV legend launched her legendary career.

“The Oprah Winfrey Show” was filmed at a studio in Chicago from 1986 to 2011—and the city served as Winfrey's home base for several years. Her property collection in the Illinois metropolis steadily evolved as her fame grew.

She is understood to have since offloaded most, if not all, of her Chicago holdings, earning a very pretty profit along the way.

In the 1990s, she bought four condos on the 56th and 57th floors of a luxury high-rise. She later sold the combined 9,600-square-foot property in 2015 for $4.6 million.

She also shed a three-bedroom apartment over the Four Seasons Hotel that she had bought in 1994 for $100,000. The unit was sold for $1,275,000 in 2015.

Winfrey went on to unload three units in a historic downtown building known as Acorn Lofts in 2013, selling one of the live-work spaces for $675,000, another for $507,000, and the third for $875,000.

She also sold a modest Colonial in Elmwood Park, IL, for $375,000 in 2018.

For many years, Winfrey's main stateside residence has been in the coastal enclave of Montecito, where her neighbors have included Prince Harry and Meghan Markle, Gwyneth Paltrow, and Ellen DeGeneres and Portia de Rossi.

Winfrey first laid down roots in California in 2001, when she purchased an extraordinary megamansion for $50 million—marking the start of her Promised Land compound. She has since added several parcels to that property.

The enormous neo-Georgian mansion on 40 acres comprises six bedrooms and 14 bathrooms in 23,000 square feet of living space.

Offering mountain and ocean views, the gorgeous grounds include a pool, stables, landscaped gardens, vegetable gardens, and a pond.

That home was just the beginning of what has since become an incomparable compound with numerous structures, including a neighboring 23.26-acre equestrian estate that she purchased for $28.85 million in 2015.

She also snagged Jeff Bridges’ longtime retreat for $6.85 million in late 2019, bringing her total holdings in the area to nearly 70 acres.

However, in recent years, she appears to have begun downsizing her California portfolio.

In 2021, the savvy investor reportedly picked up a 2-acre estate for $10.8 million and split it in two. She turned around and sold the main farmhouse with mountain and ocean views on an acre to “Friends” star Jennifer Aniston in 2023 for $14.8 million.

Two smaller cottages were sold to her friend and personal trainer Bob Greene for $2.3 million.

Then, in 2025, she offloaded a chunk of the estate she purchased from Bridges to Maroon 5 frontman Adam Levine and his wife, supermodel Behati Prinsloo, for $17.27 million.

It's understood that the couple planned to carry out some extensive renovations to the home, with their spokesperson previously revealing that they were viewing the dwelling as an "exciting opportunity." They were going to spend around a year "developing" the estate.

While she has been downsizing in California, Winfrey appears intent on growing her extraordinary estate in Hawaii, where she now owns about 1,000 acres in Maui.

Her love of the Valley Isle started in 2003, when she purchased two properties in the Kula community, before adding 23 more acres and multiple buildings to the estate for $5.3 million. She’s been a part-time resident ever since.

Multiple reports suggest that her Hawaii property purchase also included a boutique bed-and-breakfast, which is thought to be used by the TV legend to house any guests who visit her while she's staying there.

Over the decades, she has picked up even more properties in the area, reportedly spending over $40 million on 163 prime acres.

She didn’t stop there. In March 2023, local news outlet KITV reported that Winfrey had picked up 870 "agriculturally zoned" acres in Kula for about $6.6 million.

She’s said to have built a secret road to her property, making access to the more populated parts of Maui that much easier.

In addition to her Kula holdings, she purchased over 60 acres in the Hana area in 2005.

Additionally, the TV legend owns a stunning 66-acre estate in Colorado, which she purchased for $10.85 million in 2014.

It has been reported that she had plans to build a custom home on the property, which sits above the ski town of Telluride.

Clearly eager to ensure that she had somewhere to rest her head in the area, however, she chose to snap up a "temporary" home while work on her other resort property was completed, buying a high-tech Telluride mansion for $13.7 million in 2015.