After spending the night in his South Side Kenwood home for the first time in more than a year, he then walked the streets greeting the neighbors.
He was to spend the night at Camp David in Maryland Saturday after departing O'Hare International Airport on Air Force One.
The president and his senior advisor Valerie Jarrett took a four-block stroll around the neighborhood.
When a reporter asked if he had cooked breakfast, Obama said, "No, I woke up too late."
On his walk, the president encountered some excited neighbors.
One, Brian Sayles, shot video of the the president and was among those who got to shake his hand.
"He feels comfortable walking around his neighborhood," Sayles said. "We all feel comfortable having him here. And it's just great."
Elsewhere, nearby residents stood on balconies or just outside the dense security perimeter, hoping for a glimpse of the commander in chief.
"We love having him here," said neighbor Barbara Bowles. "Many of us knew him before he became president. And we feel very fortunate he is president.".
"Some people may think it's a little bit of a headache just to go through the extra security checkpoints, but ultimately I think it's a really good thing," said neighbor Isaiah Robinson.
If the presidential election were held only in Kenwood and Hyde Park, the president would win by a landslide. But polls this week show his favorability slipping, as Republican Mitt Romney and his surrogates continue hammering him on the economy.
"Since President Obama took office, millions of households across the country have seen their incomes shrink, while the cost of healthcare, food, and gasoline have greatly increased," said Texas Republican Sen. John Cornyn.
The president spoke Friday night at a fundraiser at the Chicago Cultural Center.
"We're not where we need to be," Obama said of a bleak jobs report released Friday. "We're not there yet. We saw that in today's jobs report."
Romney is doing his own fundraising in California, wooing donors at the home of a supporter in Beverly Hills.
At a cocktail party in Newport Beach, couples paid $25,000 for a photo with the presumptive GOP nominee.
It is not known how much Obama raised on his fundraising trip.