CHICAGO — Chicagoans on Tuesday were picking a new mayor in an election that came down to a choice between one of the city’s best-known, longtime politicians and a newcomer who has never held an elected post.

Whether the winner is Toni Preckwinkle, a former alderman who is president of the Cook County Board, or Lori Lightfoot, a former federal prosecutor who has cast herself as an outsider in the city’s insular world of politics, Chicago will be led for the first time by an African-American woman, making it the largest American city ever to elect a black woman as its mayor.

The new mayor — Chicago’s 56th — arrives at a pivotal moment for a Democratic city that has for the past eight years been led by Rahm Emanuel, who surprised many residents when he chose not to seek re-election.

Chicago, a city of 2.7 million residents, is wrestling with dueling realities: Tech jobs and convention business have poured into its shimmering downtown while public schools have been shuttered on the South and West Sides and thousands of black residents have moved away. Mr. Emanuel’s administration made strides to shore up the city’s fiscal woes but residents have complained about mounting taxes and fees. Chicago’s new mayor still must come up with an additional $1 billion in the next four years to continue pulling the city out of a pension crisis.

And the city says its crime problems have been improving over the past two years, recording about half as many murders this year as it did during the same period in 2016. Still, gun and gang violence are pervasive and the city had more than 550 homicides in 2018, more than in the nation’s two larger cities, New York and Los Angeles.

Race has often played an outsize role in politics in Chicago, a city that is essentially evenly split between white, black and Latino residents. On Tuesday, though, the contest between two African-American women scrambled the usual political calculus, or what one Chicagoan, Ra Joy, described as its habit of “tribal voting,” in which politicians could count on support from voters of their own race.

In February, during the most crowded mayoral primary in city history, Ms. Lightfoot and Ms. Preckwinkle topped a far larger array of candidates of various ethnicities, races and genders, removing all the others from Tuesday’s runoff. That left political alignments few Chicagoans had seen before: Ms. Lightfoot pursuing white voters on the city’s Northwest and Southwest Sides; both women seeking black voters from a base on the South Side that had leaned toward a different black candidate in February; parts of Chicago’s North Side lakefront loaded with signs for Ms. Lightfoot.

Some residents said the history-making nature of the election — regardless of the winner — was energizing. But others seemed nonchalant, perhaps partly because Chicago has already seen such milestones. In 1983, the city picked its first black mayor, Harold Washington, in a racially charged election; a term before that, in 1979, the city chose its first female mayor, Jane Byrne.

In many ways, the election transformed into a referendum on Chicago’s political culture, known for its miserable ranking on most measures of corruption, its political machine and its habit of keeping family dynasties in power.

Ms. Lightfoot, who was partner at a prominent law firm, Mayer Brown, portrayed her status as a political newcomer as a sign of strength, pledging to dismantle City Hall’s old political ways and to “bring in the light.”

That resonated with some voters. Nora Handler, 63, a North Side resident, said she voted for Ms. Lightfoot because of her outsider status as well as a pledge to improve how the police interact with people with mental illnesses.

“In Chicago, we talk about the ‘Chicago Way’ and the machine politics,” Ms. Handler said. “I thought she was not involved in any of that.”

Ms. Preckwinkle, the longtime Cook County board president, tried to cast her experience as essential for managing a city the size of Chicago, while simultaneously reminding voters that she had — when she was first elected as an alderman years ago — regularly bucked the political establishment.

Ms. Preckwinkle’s record won a vote from Matt Smith, 30, a Ph.D. candidate at Northwestern University, who voted in Rogers Park on the Far North Side on Tuesday. “I don’t think she’s perfect, but I think she has the more progressive record,” he said. “I wasn’t too excited about Lori being a former federal prosecutor.”

As the election season played out, impatience over political corruption seemed to intensify among voters, in part because a major corruption scandal was unfolding at City Hall. Federal authorities have accused the City Council’s longest-serving alderman, Ed Burke, of running an old-school shakedown, even as the local news media reported that a second alderman had cooperated with the authorities, secretly recording his conversations at City Hall for months. Of the city’s 50 aldermen, 15 seats were up for runoff elections on Tuesday, but Mr. Burke, who has denied any wrongdoing, won re-election to another term in February, winning a margin large enough to avoid a runoff.

In recent weeks, the campaign for mayor had grown intense, boiling over with angry exchanges during debates and back-and-forths over ads and endorsements. In truth, though, the two candidates appeared to have relatively few major policy differences.

Both Ms. Lightfoot and Ms. Preckwinkle portrayed themselves as progressives. Both talked about bringing more equity to Chicago, ensuring that top-level education, affordable housing and investment ought to be spread more fairly across a long-divided city, not limited to white neighborhoods or to wealthy neighborhoods on the city’s North Side.

For Abraham Lacy, 33, a Chicagoan who was voting on the South Side on Tuesday, the city was facing urgent challenges with finances, schools and crime — challenges that may need someone with deep experience.

“At this point in time, you need someone in there that’s going to really do the job,” Mr. Lacy said after casting his ballot for Ms. Preckwinkle at an elementary school. He added: “It’s tough to have someone new come in when you have this many things going on.”

In the end, many voters said they were driven more by their perceptions about politics than about policy. Ms. Lightfoot, her supporters said, offered the promise of a new order and a rejection of the politics of a generation ago.

“It’s because of Chicago,” Deepti Pareenja, 37, said, after casting her ballot on the city’s Northwest Side for Ms. Lightfoot, in part because of the candidate’s status as a political outsider. “We have a history of corruption with people who’ve been ingrained in politics for multiple decades.”

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