Revisit the Obamas' History in Chicago As the Obama Presidential Center Opens
Daniel Hautzinger
June 17, 2026
As the Obama Presidential Center opens in Jackson Park on Chicago’s South Side more than a decade after the city was selected as its home, it’s worth looking back on why the Center is here at all. Barack Obama was born in Hawaii but eventually found his way to Chicago, met his future wife Michelle Robinson here, and launched his meteoric political career here.
The Obamas still have a house in the Kenwood neighborhood, about two miles from the Obama Center, even if they don’t spend much time there these days – they also own property in Washington, D.C., in Martha’s Vineyard, and on Oahu. They bought the Kenwood house after Obama was elected U.S. Senator in Illinois, but their roots in Chicago reach much deeper.
Michelle Robinson was born in Chicago, spending her first year and a half in Woodlawn before her family moved to a second-floor apartment in a modest bungalow in South Shore, the lakeside neighborhood south of Jackson Park, which was at time becoming a majority Black neighborhood as white families left for the suburbs. (The bungalow is visible in a new portrait of the Obamas at the Obama Presidential Center.)
“Everything that I think about and do is shaped around the life that I lived in that little apartment in the bungalow that my father worked so hard to provide for us,” Michelle said later. She attended nearby Bryn Mawr Elementary, where she was salutatorian, while also enrolling in an accelerated learning program at Kennedy-King College. She then went to the new Whitney Young High School on the Near West Side, riding the CTA for an hour or more in each direction.
She followed her brother Craig Robinson to Princeton University and then went on to Harvard Law the same year a recent Columbia graduate named Barack Obama moved to Chicago. Obama had grown up mostly in Hawaii, with a stint in Indonesia after his Kenyan father left his Kansan mother and she married an Indonesian graduate student. He lived with his maternal grandparents in Hawaii to attend a prestigious school before going to Occidental College and then transferring to Columbia. After working as a professional for a time in New York City, he landed in Chicago.
Michelle was aware of the difference between her childhood in a majority Black neighborhood in Chicago and Barack’s as one of the only Black children he knew in Hawaii. “If he had been the same kid growing up on the South Side of Chicago, I think his outcomes might be a bit different. But there wasn’t a lot of trouble to get in in Hawaii,” she told WTTW’s Elizabeth Brackett in an extensive profile in 2004 while he was running for U.S. Senate. “You could screw up in Hawaii and still be ok.”
Explore other sites near the Obama Presidential Center in the neighborhoods that shaped the Obamas.
Finding a Path in Chicago
Obama was seemingly still finding his path when he came to Chicago in 1985 to work as a community organizer on the far South Side, in Roseland and the housing project Altgeld Gardens. But the experience of working with Black communities and churches was formative. “I think the most important chapter in Barack’s life is his first three years here in Chicago,” the biographer David Garrow told WTTW’s Chicago Tonight in 2017. Obama himself agreed, writing of his years as a community organizer in his 2020 memoir A Promised Land, “But if my own impact on Chicago was small, the city changed the arc of my life.”
Inspired by Harold Washington, Chicago’s first Black mayor, who was elected through a multi-racial liberal coalition, Obama decided he could make more of an impact in electoral politics rather than community organizing and set off for Harvard Law.
He once again just missed Michelle, who returned that year to Chicago to work at the illustrious law firm Sidley & Austin. It was there that she finally met Barack in 1989, when she was assigned as his minder at the law firm while he worked there for the summer. They became a couple, their famous first date memorialized both in the fictionalized film Southside with You and in a plaque on a rock at E. 53rd Street and S. Dorchester Avenue where they had their first kiss outside a now-gone Baskin-Robbins.
After graduating from Harvard Law as a highly qualified candidate – he was the first African American to head up the prestigious Harvard Law Review – Barack returned to Chicago and worked on a voter registration project before surprising some by taking a job at a relatively small firm, Davis, Miner, Barnhill & Galland, that did civil rights work. He lived for a time with Michelle in her childhood home in South Shore.
They married in 1992 at Trinity United Church of Christ in Washington Heights, which Barack had begun attending during his organizing days. (The name of his second book, The Audacity of Hope, came from Trinity’s pastor Jeremiah Wright, who married them.) The reception took place at the South Shore Cultural Center, a lakefront palace that had formerly housed a country club that excluded Black and Jewish people. Jesse Jackson’s daughter Santita, a close friend of Michelle’s in high school, sang Stevie Wonder at the reception.
Obama published his first memoir, Dreams from My Father, and the new couple purchased a “modest but cozy condo in Hyde Park, right across from Lake Michigan and Promontory Point,” in Obama’s words in A Promised Land. They were down the street from Michelle’s brother and not too far from her mother, who still lived in the family South Shore home and hosted family gatherings filled with soul food there.
Diving into Politics
When his local state senator decided to run for a congressional seat opened by scandal, Obama decided to dive into electoral politics with the support of, among others, his local alderwoman Toni Preckwinkle. He announced his run on September 19, 1995 at a Ramada Inn in Hyde Park “with pretzels and chips and a couple hundred supporters–probably a quarter of whom were related to Michelle,” he wrote in A Promised Land. He won.
He wrote a regular column for the Hyde Park Herald but sought bigger fields, deciding to make an ill-advised run against Bobby Rush for Congress in 2000. It’s the only election he ever lost.
He considered leaving electoral politics in this period, when he also had two young children at home whom Michelle was shouldering the brunt of caring for: Malia had been born in 1998, and Natasha, known as Sasha, was born in 2001. Michelle had left law behind. At a job with the City of Chicago’s Department of Planning and Development, her boss was Valerie Jarrett. Jarrett would become a close friend and adviser in government and life to both Obamas, and is now the CEO of the Obama Foundation, which administers the presidential center.
Barack Obama also filmed an appearance for WTTW’s Check, Please! around this time, although the episode did not end up airing. He recommended Dixie Kitchen in Hyde Park, but was also known to frequent the no-frills Valois Restaurant in the neighborhood. In his book The Audacity of Hope, he named the West Side soul food spot MacArthur’s as another favorite. In later years, he and Michelle were known to frequent Spiaggia and Rick Bayless’ restaurants near downtown; Bayless was rumored to be one of their choices for White House chef. And Obama got his hair cut by the same barber at Hyde Park Hair Salon for over 20 years.
Obama eventually decided to run for the U.S. Senate, seeing an opportunity when the Republican incumbent Peter Fitzgerald decided not to run for re-election in 2004. Obama’s trusted advisor David Axelrod initially advised him to wait for Richard M. Daley to retire and run for mayor of Chicago rather than try to leap to such a prominent position. But Obama staked out a space, notably speaking at a rally against the Iraq War in downtown Chicago in 2002 when few elected officials were doing so. Obama won the Democratic primary and then faced an easy general election after his Republican opponent resigned due to a scandal and was replaced by an out-of-state firebrand. Obama became senator by the biggest margin in Illinois history.
Michelle had by now left the city to work for a nonprofit youth leadership program and then the University of Chicago, first in its school and later for its hospital system. The Obamas purchased a large home in Kenwood across from a synagogue, which they still own today.
Obama had immediately won a national profile before he was even elected U.S. Senator after being invited to give a memorable speech at the Democratic National Convention in 2004 by presidential candidate John Kerry. He eventually decided to take another audacious leap and run for president himself in 2008.
On election day, he and Michelle voted at Beulah Shoesmith Elementary School in Hyde Park in the morning. He then played basketball – an election day ritual he had developed during the presidential primary – before heading to a hotel downtown to watch the results come in. When he was declared winner, he headlined a massive rally in Grant Park.
And with that, the Obamas were off to the White House.
