The visit comes on the heels of his announcement that he has officially begun his bid for re-election, and is setting up campaign headquarters here in Chicago.
Thursday's fundraiser will be at Navy Pier, and will include an appearance by Bull's star Derrick Rose.
By operating his re-election campaign from Chicago, Obama will try and do what no incumbent president has done in decades: win re-election with a campaign headquartered outside of Washington D.C.
Obama's advisers hope a Chicago location could insulate his campaign from some of the Washington chatter and news leaks that often plague campaigns. A beyond-the-Beltway headquarters could allow them to offset the notion that Obama, who campaigned as an outsider above the partisan fray and promised a new approach to politics, has become the ultimate political insider.
"Basing it in Chicago says, 'I'm not of Washington,' but if he doesn't spend time in Chicago, he is of Washington," said Paul Light, a public service professor at New York University.
Obama's relationship with his town has evolved over the years.
He was a community organizer, worked on a major voter drive and practiced law in his early days in the city. When he entered politics, he focused on the state capital of Springfield, and cast himself as above the brass-knuckled nature of Chicago politics, whose history is pockmarked with corruption and scandal.
During the 2008 campaign, Obama was a fixture in Chicago when he wasn't crisscrossing the country for votes. He took his wife, Michelle, around town to dinner at some of the city's best restaurants. He hung out with his daughters. He worked out at the gym. He played basketball with his buddies. He attended meetings at his campaign office, all under the watchful eye of reporters and Secret Service agents. His family, friends and neighbors talked openly about the candidate and his lifestyle.
As president, Obama has made only about a half a dozen visits to Chicago, often to raise money for candidates. He's made only a few overnight trips to his South Side house.
His neighbors don't seem to hold it against him.
"He's got a whole world to deal with," says Hosea McKay, a 73-year-old retired substance abuse counselor, who lives several blocks away. "Chicago, we can't be so egotistical that we think he's supposed to pop in every three or four months and hang out with us."
The Associated Press contributed to this report.