There was intense security around the property as Trump made a rare overnight stop in the deeply Democratic city.
Down the street, that opponent party was celebrating.
With fewer than 40 days until the election, the statewide party's annual gala served as a small-scale repeat of the Democratic National Convention and a call to action.
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"We are taking buses to Wisconsin and Michigan," said Cook County Democratic Party chair Toni Preckwinkle. "We are not trying to convert Trump voters, we are trying to get our own people to vote."
Michigan Governor Gretchen Whitmer reminded Democrats how slim the margin is.
"In 2016, Donald Trump won Michigan by two votes per precinct," she said.
Trump made two separate campaign stops in Michigan Friday.
"We have early absentee mail in voting in your state starts this week. And if you have your ballot, return it as soon as possible. And if not get a ballot, go out and get a ballot," he told voters.
Michigan is one Midwestern piece of must-win territory for both candidates; a state that's won, and cost, each party in the last election.
Gov. Whitmer is working to pull ahead in that equation.
"Everyone counts," she said. "All across the state, in all counties, we are working to make sure people know it's easier to vote than ever in the state of Michigan."
Illinois Democrats said they raised another $1 million at the event Friday.
Trump is set to depart from his Chicago property Saturday morning for a campaign event in Wisconsin.