Tuesday's election will be a one-and-done event if any candidate receives one vote above 50 percent support.
With polls showing Emanuel hovering around that threshold, candidates are opening up multiple lines of attack.
Emanuel spent Saturday shaking hands on the city's South Side even as his North Shore roots are the subject of candidate Gery Chico's latest ad.
"I grew up in back of the yards and worked at my father's gas station," Chico says in his ad. "Rahm grew up in suburban safety and privilege."
On Saturday night, Chico cheered on Simeon at the annual City vs. Suburban basketball showdown and drew his own election day comparison.
"You are where you come from, and you're most likely to behave based on what your experiences have been," Chico said. "And I think that's why he's more willing to impose taxes on working families. We call it the Rahm Tax."
Emanuel, who grew up in Wilmette, is firing back with an ad of his own.
"Gery Chico is back on the attack, this time hitting Rahm for the neighborhood where he was raised. But who's fought for our neighborhoods?" Rahm's ad says.
The ad battle reflects a fundraising battle in this run up to Election Day.
Since January 1, when new fundraising laws took effect, Chico has matched Emanuel nearly dollar-for-dollar although Emanuel's overall campaign war chest remains dominant.
"All the TV ads, the huge spin machine, the unlimited money cannot get past what you have already done, what team you're playing on, what interests you represent, what you are going to do to the people of the city of Chicago," said mayoral candidate Carol Moseley Braun.
On Saturday, less-funded candidates Moseley Braun and Miguel del Valle questioned whether Emanuel's money reflected his loyalties.
Disclosure reports show much of Emanuel's recent contributions have come from high-powered Chicago law firms.
"I talked to a friend who is a lawyer who's with a law firm downtown who said to me, 'Sorry Miguel, I've got to go with Rahm Emanuel because my firm said I got to go with Rahm Emanuel because if we don't, we're not going to get any business,'" devl Valle said.
At a forum Saturday, candidate Patricia Van Pelt-Watkins also made her case for a run-off election saying voters need more time to evaluate candidates on the issues.
If there is a two person run-off, we can probably expect more negative ads.
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