The two-day event kicked off Tuesday at the Illinois Institute of Technology in Bronzeville on the South Side.
The former president was interviewed by actress Yara Shahidi.
"Worry more about what you want to do rather than what you want to be," the former president advised.
Young dancers from the Joffrey Ballet started the event, which is aimed at helping future leaders find their way.
Michelle Obama was joined by her older brother Craig Robinson. She spoke about growing up on Chicago's South Side and going to Princeton University.
"What I didn't know that I was getting into by going to one of the iviest of the Ivys was sort of the isolation of being one of a few black students, blacks students from an urban environment like Chicago," she said.
"There's so many different lessons that I learned from my Dad the years we had him. But none more than hard work," said Robinson.
"It was just amazing to hear her speak and talk about her experiences on the South Side. I'm from the South Side, it was such a great connection to make with her," said Nyia Hawkins, Joffrey Ballet Exelon Strobel dancer.
The summit will feature civil rights activists and celebrities such as Ava DuVernay, legendary singer Mavis Staples, as well as Chicago artist Theaster Gates. This year's event will also showcase a 3-D version of the Obama Presidential Center, including a look at the proposed landscape of Jackson Park's historic Women's Garden.
Hundreds of participants will meet amid the cultural inspiration and technical innovation to see the updated plans for center.
"Imagine Chicago as the hub, the global hub, where there is a network of people who want to make their communities better," said David Simas, Obama Foundation CEO.
WATCH: Obama Foundation releases renderings of the Obama Presidential Center
The park will be restored with plantings, pathways, and new seating as well as plans for a one-acre wetland area and a place for children to play.
President Donald Trump was in Chicago Monday morning to speak at the International Association of Chiefs of Police conference at McCormick Place. He called the city an embarrassment to the U.S.
Meanwhile, construction of the actual center is on hold pending a federal review, but some say the area around Jackson Park is already changing.
In advance of a bankruptcy auction of Woodlawn properties, some rallied for Community Benefits Agreement to protect longtime residents from potentially being forced out.
"Please think about the people in the community. It's not just luxury condos and hotels," said Kyana Butler, area resident.
Kellye Winbush lives in Woodlawn and says she is thinking about the community as they plan to develop affordable rental units with their two newly purchased properties.
"We were able to get a piece of the pie, that's where it starts. You have to get a small piece and do the best we can with that," Winbush said.
The future of the area around the site and empowering the next generation of leaders will likely be among the remarks of former President and First Lady Obama when they return to Chicago Tuesday.
For more about the Obama Foundation, visit their website: www.obama.org.