Air Force One touched down at O'Hare Airport around 4:40 p.m. The president will spend the night at his home on the city's South Side. The first lady and their daughters are not with the president.
His first event -- a reception with about 350 people with tickets starting at $2,500 -- got under way at 5 p.m. at Chicago's Cultural Center in the Loop. During a half hour speech that focused on the economy, Obama criticized Republican candidate Mitt Romney's vision for the country as the "one that got us into this mess in the first place."
Employers in the United States added only 69,000 jobs in May, the fewest in a year and not even close to what economists expected. For the first time since last June, the unemployment rate rose, to 8.2 percent from 8.1 percent.
"We're not where we need to be," Obama said. "We're not there yet. We saw that in today's jobs report."
The president only briefly mentioned the Labor Department report. He spent more of his speech reminding Americans of the economy he inherited from the previous administration.
"The month I took office we lost 800,000 jobs, eight million all total," he said. "When we embarked on this journey in 2008, it wasn't to get back to where we were before the financial crisis. The idea was to start fixing things in a more fundamental way."
Hours earlier, presumptive Republican nominee Mitt Romney blamed administration policies for the 8.2 percent unemployment rate.
"Their policies have not worked," Romney said. "And in many respects their policies have made it harder for the economy to recover."
With a stop in Minnesota before Chicago, it was the 146th presidential fundraising trip since Obama's inauguration by a Republican count.
"So he's not working for the people, he's working for himself, and I think that's really going to help us in November," said Pat Brady, Illinois Republican chairman.
Local Republicans phone banked before the president's arrival, trying to motivate their voters in a state where the incumbent is expected to win 20 electoral college votes.
"Not only is he a Democrat in a state that has been tending Democratic, he's also a favorite son candidate of the state," said Prof. Dick Simpson, University of lllinois at Chicago.
After an event at the Chicago Cultural Center, the president attended two smaller, pricier fundraisers -- dinner at a private home on the South Side and a reception for wealthy supporters on the city's Gold Coast before heading home to Kenwood Friday night.
"I am sleeping in my bed tonight," he said. "I'm going to go into my kitchen, I might cook something for myself, putter around in the backyard a little bit. It's good being home."
Security tight around Obama's Kenwood home
The president has not spent a lot time at his South Side home since he was elected. When he does return, his visit creates quite a buzz in the Kenwood and Hyde Park neighborhoods.
Concrete barricades, Chicago police, and Secret Service surround Obama's home 24 hours a day. But when he is spending time there, security gets even tighter. Because of the chaos it can cause, President Obama hasn't stayed there in many months.
Neighbor Renita Jones has been living near the president for two years now and is used to being in a heavily guarded area.
"He needs the security, I would expect no less for our president," Jones told ABC7. "It's a little annoying that instead of coming straight up the boulevard, you have to go around, but it's not really a big deal."
Members of the KAM Isaiah Israel Congregation, a synagogue across the street from the president's home, have developed a working relationship with the Secret Service. Some members are even friends with the first family. Services on Friday will coincide with the president's stay at home.
"We work with the Secret Service to enable that our membership and our guests have access to the building whenever we have activities going on regardless of whether or not is physically in residence," said Tal Rosen, former director KAM Isaiah Israel Congregation.
But Noel Morical, a dog walker, isn't used to all of security. Walking "Luke" the dog Friday has been a bit of a challenge.
"I just have to be a little more aware of where I'm walking, so I don't have to clash with security," she said.
Luke's owner lives in the neighborhood and warned Morical about the potential headache.
"You just have to be more prepared, and luckily my boss is kind enough to provide me with information on the best roads to take what areas to avoid," Morical said.
The security perimeter is about three blocks long but as the president makes his way home Friday night, it is expected to widen. Residents must show their ID to Secret Service agents to pass through the barricades.
The Associated Press contributed to this report