Voters in Tuesday's election will cast ballots that for the first time in more than two decades do not have Daley's name on the list. And they may select the city's first Jewish mayor, Rahm Emanuel. Or the first black woman, former U.S. Sen. Carol Moseley Braun. Or the first Hispanic mayor - either former Chicago public schools president Gery Chico or City Clerk Miguel del Valle.
The five-month campaign took all kinds of unusual turns, even for a city where voting from six feet under is part of election lore. But after a race that included a challenge of Emanuel's right to call himself a Chicagoan going all the way to the Illinois Supreme Court and Braun accusing another candidate of being strung out on crack cocaine, some voters complained they had not heard enough about where the candidates stood on the issues.
Some said they were focused more on the candidates' resumes and influence.
"Daley had connections," said Terrence Trampiets, 66, a North Side resident intending to vote for Emanuel. "You have to have that to get things done."
The campaign began with Daley's stunning announcement last fall that he would not seek a seventh term. Suddenly a race that looked like it might be boring, with many Chicago residents certain that the incumbent Daley would easily outdistance whatever competitors stepped forward, as he had six times before.
Nearly two dozen politicians, from the county sheriff to congressmen to state lawmakers to members of the City Council, made noises that they were at the very least considering a run.
The campaign focus quickly shifted from City Hall to the White House. There, Obama bid farewell to Emanuel and wished him luck in the next chapter of his life, which everybody knew but nobody said included running for mayor of Chicago.
That was followed by a sometimes downright weird tussle over whether Emanuel was a city resident and therefore even eligible to run because he had not lived in Chicago for a full year before the election, as required by law. He had lived in Washington working for Obama since soon after giving up his North Side congressmen's seat in 2008.
The residency challenge turned into a spectacle that saw Emanuel on a Board of Elections witness stand in a makeshift courtroom in the basement of a downtown building being grilled for a dozen hours by regular Chicago residents with some very irregular questions, such as one from a man who asked if Emanuel had been involved in the 1993 Branch Davidian siege at Waco, Texas, when he worked for the Clinton administration.
Several tense days followed when an appellate court ordered Emanuel's name thrown off the ballot, before the state's Supreme Court stepped in and definitively ruled that Emanuel was a resident and could indeed run for mayor. Until then, Emanuel's rivals had painted him as an outsider.
Meanwhile, a group of African-American leaders, including the Rev. Jesse Jackson, decided that their best hope of electing a black mayor was to convince all but one of the major black candidates to drop out of the race. Both U.S. Rep. Danny Davis and State Sen. James Meeks, the pastor of a megachurch on Chicago's South Side, ended their candidacies and threw their support behind Braun.
The city's first black mayor was Harold Washington, who was elected in 1983. The first woman mayor was Jane Byrne, elected in 1979.
The black consensus effort marked a return to the spotlight for Braun, who last won election in 1992 when she became the first African-American woman to win a U.S. Senate seat. She had largely been out of the spotlight since she announced a longshot bid for the Democratic nomination for president in 2004.
But Braun made headlines when, after rival Patricia Van Pelt-Watkins wondered aloud at a debate about Braun's absence from public life, Braun shot back that the reason Van Pelt-Watkins didn't know what she'd been up to was that she had been "strung out on crack."
Van Pelt-Watkins said afterward she'd had a drug problem years ago, but denied ever using crack, and Braun later apologized. But she has often shown sharp elbows during the campaign in exchanges with Emanuel and even calling a local newspaper columnist. Some polls had her stuck in single digits or the teens while Emanuel scored well above 40 percent.
Patrick Johnson, a 41-year-old carpenter, said he is voting for Emanuel, in part because he did not hear enough from the other candidates. "There was an inability to promote themselves," he said.
Another voter, Lucinda Williams, said she too is voting for Emanuel - in large part because he knows Obama. "I mean, he's the president," she said.
Others said they weren't impressed by what they heard during the campaign, particularly Braun's remarks about Van Pelt-Watkins.
"That drove people toward Emanuel," said Randolph Wells, a 46-year-old employee with United Airlines who lives on the city's Southwest Side. He said he was voting for Emanuel because he thinks the former White House chief of staff is best equipped to fix what ails the city: "All that mudslinging, that split-splat."