The president plans to make a personal appearance at the International Olympic Committee's host city selection in Copenhagen, Denmark, on Friday. He will join his wife, Michelle, who is leading the U.S. delegation, along with senior adviser Valerie Jarrett.
Obama would be the first U.S. president to take on such a direct role in lobbying for an Olympics event. Chicago faces tough competition from Rio de Janeiro, Madrid and Tokyo.
The president, who plans to leave Washington, D.C., late Thursday, is likely to echo remarks he made on behalf of Chicago at a recent White House event.
"I've called Chicago home for nearly 25 years. It's a city of broad shoulders and big hearts and bold dreams. A city of legendary sports figures, legendary sports venues and legendary sports fans. A city like America itself, where the world -- the world's races and religions and nationalities come together and reach for the dream that brought them here," Obama said on Sept. 16.
A White House statement Monday said the president will arrive "just prior" to Chicago's turn before the committee, and that he and the first lady will both make presentations.
"They will discuss why Chicago is best to host the 2016 Summer Games, and how the United States is eager to bring the world together to celebrate the ideals of the Olympic movement," the statement said.
Obama, who represented Chicago's state, Illinois, in the U.S. Senate after serving in the Illinois Legislature, is a longtime supporter of the city's bid. He and Michelle consider Chicago their adopted home town, and he recently sent letters to selected IOC members, promising a "spectacular Olympic experience for one and all."
"President Obama and First Lady Michelle Obama symbolize the hope, opportunity and inspiration that makes Chicago great, and we are honored to have two of our city's most accomplished residents leading our delegation in Copenhagen," Mayor Richard M. Daley said in a statement.
The president had held off on announcing a trip to Copenhagen, saying his first priority was the ongoing debate in Washington over health care reform. The legislation is a signature piece of his domestic policy agenda and negotiations in Congress have been contentious.
With the health care debate still brewing, Iran stoking international concerns over its nuclear program and a decision pending on how to deal with the rising violence in Afghanistan, the president will be leaving at a key time for his administration.
However, the trip is scheduled to be brief, according to White House aides.
With heads of state representing Rio and Madrid already scheduled to attend the IOC meeting Friday, Chicago's bid organizers had hoped Obama would make an in-person appeal.
"I don't think there's an IOC member on the planet that wouldn't love to meet your president. He's a transformational figure in the world today," longtime IOC member Dick Pound said recently.
Obama is also mobilizing his administration on behalf of Chicago's bid. Senior adviser Jarrett, Education Secretary Arne Duncan and Transportation Secretary Ray LaHood, will also be joining the president and first lady in Copenhagen. All are from Illinois.
They join a Chicago contingent already packed with more star power than a Hollywood red carpet. The first lady is one of the few people who rivals her husband in visibility, and she'll be joined by talk show host Oprah Winfrey, who trails only Angelina Jolie on Forbes' annual Celebrity 100 list, a ranking of the rich and famous' most powerful.
FOX News' Mike Emanuel and Kelly Chernenkoff and The Associated Press contributed to this report.