CHICAGO — In one of the most unpredictable, wide-open Chicago elections in generations, residents went to the polls on Tuesday to pick a replacement for Rahm Emanuel as mayor of the nation’s third-largest city.

With 14 candidates — more than this city has ever seen before in a mayor’s race — it was uncertain how much would even be known by day’s end. No candidate was expected to win more than 50 percent of the vote, but the balloting was expected to winnow the choices to two people and a runoff election on April 2.

[More on the issues at stake in Chicago’s election.]

Campaign forums have often looked like a reunion of Chicago’s best-known political figures — a former police superintendent, a former public schools chief, a former police board head, a former city clerk.

Among the names familiar to voters: Toni Preckwinkle, the Cook County board president and chairwoman of the county’s Democratic Party; Susana Mendoza, the state comptroller; and William M. Daley, a brother of this city’s longest-serving mayor (Richard M.) and a son of the second-longest-serving mayor (Richard J.).

But with so many candidates and no clear favorite, the race was seen as up for grabs — a rare circumstance in a city where mayors have more often held office for long stretches and where incumbents are usually on the ballot. Richard M. Daley, who ran Chicago for 22 years before Mr. Emanuel arrived in 2011, was sometimes known as “Mayor for Life.”

So many choices seemed to have left some Chicagoans flummoxed — unsure, even in the final hours, whom they would vote for. Some political strategists said they wondered if that might discourage some people from voting at all in the election, which is technically nonpartisan, though Democrats reliably win.

As voters streamed into a polling place in Rogers Park, on the city’s Far North Side, many said they were disappointed with the choices, even if there were a lot of them.

“I still haven’t made up my mind,” said Brian Koch, 58, a retired computer programmer, as he walked down a snowy sidewalk in front of Sullivan High School.

He had only one guiding principle in mind: If a candidate had been in politics too long, he’d be voting for someone else. “If they’re in, get them out,” Mr. Koch said. “There’s just so many of them and a lot have a bad history.”

[Everything you need to know about the top candidates for Chicago mayor.]

By midday, Chicago appeared to be headed for historically low voter turnout. Fewer than 300,000 ballots had been cast, including mail-in and early votes, from among the city’s 1.5 million registered voters, said Jim Allen, a spokesman for the Chicago Board of Election Commissioners.

“If there was ever a time when your vote counted more, I can’t think of one,” he said.

Mr. Emanuel upended Chicago’s political landscape when he announced in September that he would not seek a third term. Mr. Emanuel — who had been sharply criticized over his handling of school closings, crime and police misconduct and had faced political challengers — said at the time that the mayor’s office “has been the job of a lifetime, but it is not a job for a lifetime.” After that, many more candidates stepped forward.

Whoever becomes the next mayor of this city of 2.7 million people will face an array of complicated, sometimes interconnected, challenges all at once.

The city’s pension system will require an additional $1 billion in revenue by the end of the new mayor’s first term. Yet residents say they are weary from years of increases in their property tax bills and fees. Crime and gang violence remains a deep worry for many, even as the city contends with its long history of troubled relations between the police force and residents, especially in the black community.

And although tourism has boomed downtown, development along the Chicago River has flourished and corporations have flocked to the city in recent years, some neighborhoods on the South and West Sides have struggled with disinvestment, schools closing and people moving away.

On Tuesday, Jackie Ropski, a marketing director for an elementary school, said that she saw this election as more important than some, with so many candidates to choose from and at a pivotal moment in Chicago history.

“I think there is a certain amount of weight on this particular election,” Ms. Ropski said, after voting in the Irving Park neighborhood on the Northwest Side. “Personally, I think education takes prominence among all the issues, but whoever is mayor has to take a layered approach. How do you solve poverty, crime, neighborhood tensions, education? That’s complex.”

Jewel Morris, 62, a retired probation officer, said he had voted for Ms. Preckwinkle, though he deemed her the “lesser of two evils” compared with William Daley, who is known as Bill.

“No Daleys, no Bushes, no dynasties,” said Mr. Morris, who lives on the Near West Side. “We don’t need any of that.”

The Chicago of 2019 is better than when he was a child, he said. The architecture is unparalleled, the restaurants are world-class and tourists are coming to the city in droves. But the inequality feels like the Chicago of his youth.

“You’re looking at a tale of two cities,” he said. “It’s still the city of neighborhoods and still the city of segregation.”

At Manny’s deli, south of downtown, Natalie Wasso said she was leaning toward voting for Mr. Daley, if she voted at all.

Ms. Wasso, 32, a phlebotomist who lives on the Southwest Side, said she trusted the Daley family, which led the city for most of her childhood. Her grandmother had always voted for Daleys in past elections.

“We never had a problem: That’s the name we know in Chicago,” Ms. Wasso said. “He can relate to us regular people.”

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