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At the time, Ms. Lightfoot was one of only a handful of figures willing to run against Mr. Emanuel, who was widely expected to appear on the ballot until announcing in September that he would not. As the field of candidates grew more vast, including the entrance of Ms. Preckwinkle, Ms. Lightfoot forged ahead with her campaign.

There were reasons for skepticism: Ms. Lightfoot was relatively unknown in the city’s political realm, and her ballot petition signatures were briefly challenged last year. But she surged in at least one poll in the final days before the February election, and was endorsed by The Chicago Sun-Times.

“She has the vision, values, qualifications and policies to be an effective leader for the whole city, from the hedge fund managers to the fast food workers,” the newspaper’s editorial board wrote. “She is calm, focused, principled and independent.”

In the weeks since, as the race took on a venomous tone, Ms. Lightfoot tallied up endorsements across the city, including from several of her former opponents.

Ms. Lightfoot repeatedly portrayed Ms. Preckwinkle, with whom she agrees on most major policy issues, as a part of the Democratic machine that long dominated Chicago government.

Ms. Preckwinkle was fond of noting Ms. Lightfoot’s work as a “corporate lawyer” and her service in city government under the previous two mayors. And Bridget Gainer, a county commissioner who supported Ms. Preckwinkle, said her candidate’s political experience was in fact an asset.

“We need results, not just rhetoric,” Ms. Gainer said in February. “Chicago is not a training wheels job.”