One voter took a little convincing to believe she was on the phone with President Obama.
"You have to tell the whole team over there we appreciate them. It's going to depend on whether the votes turn out," Obama said.
On Tuesday, Obama told a newspaper he had two speeches ready for Election Night. It's the first time the president suggested something other than victory.
He and first lady Michelle Obama will watch the election returns from their Kenwood home, where they stayed overnight, on the city's South Side before attending his event at Chicago's McCormick Place.
Obama shot hoops on the city's West Side at the Hope Athletic Center with friends, including former NBA player Scottie Pippen, former 2010 senate candidate Alexi Giannoulias, former NBA star Randy Brown and U.S. Secretary of Education Arne Duncan. Basketball is an Election Day ritual for Obama that has been observed since his 2008 primaries.
"It is good camaraderie," said Arne Duncan, U.S. secretary of education and former Chicago Public Schools CEO. "We did this four years ago and it was a good luck charm then and hopefully again tonight."
According to twitter posts, Obama's team won by about 20 points.
"It was a good opportunity to let the president put his guard down and have some fun with his friends and win a basketball game. There is a great tradition. It is kind of bittersweet, but it was a lot of fun," Giannoulias said.
After the game, the president returned home for a bit before going to the Fairmont Hotel to join Vice President Joe Biden. The two are doing TV and radio interviews with local stations in battleground states.
It's not clear when he and the first lady will greet thousands of supporters -- staffers and campaign volunteers -- at McCormick Place. Their daughters, Sasha and Malia, flew in with their grandmother after school on Tuesday afternoon.
"We have lots of people go to Wisconsin from Illinois. Those are the people who are going to receive tickets and have access to this event. It is about encouraging people to be part of history, the part of this campaign ," Melanie Roussell, DNC national press secretary- campaign spokesperson, said.
Two thousands credentialed journalists from all over the world will also be at McCormick Place. Lorenzo Mila Is the Washington, D.C. Bureau chief for Spain's Eurovision.
"We still have that picture of 2008, of a president trying to reach the world in a different way," Mila said.
The atmosphere at McCormick Place is quite different than four years ago when Obama spoke after being elected to crowds at Grant Park. Still, campaign spokespeople insist the same energy will electrify on election night.
"It is as historic. Last night was the president's last campaign speech ever. Tonight will be his last victory speech ever ," Roussell said.
Obama will play basketball with some buddies - an Election Day tradition- at a Chicago gym. He will do satellite interviews with local TV stations in battleground states, but will not leave Chicago on Tuesday.
"This is it. This is the last time we have. We don't want to preoccupy our volunteers and voters with events when we really want to be driving them to the polls ," Roussell said.
Republican presidential nominee Mitt Romney continues to campaign on Tuesday in those battleground states.