The Chicago mayoral election of 1999, which took place on February 23, 1999, resulted in the re-election of incumbent Richard M. Daley over Bobby Rush, with 428,872 votes to Rush's 167,709. Daley garnered a landslide 71.9% of the total vote, winning by a 44-point margin. This was the first officially nonpartisan Chicago mayoral election, per a 1995 Illinois law.
Daley was considered a broad front-runner from the start. Nevertheless, to dedicated significant funding and manpower to his campaign, and also gave support to several aldermanic campaigns.
Joe Banks Jr. was denied inclusion on the ballot due to issues regarding the filing of his nomination papers. This left Rush as Daley's sole opponent. Rush was a well-known figure in the city. A congressman, Rush had first made his name in Chicago in the 1960s as a local Black Panther leader, and had received further notability thereafter as a member of the Chicago City Council.
The Chicago Tribune wrote of Daley's campaign,
The Chicago Tribune also observed,
Daley adopted a tactic of ignoring Rush, refraining from saying his opponent's name during campaign speeches. As was the case in all of his reelection campaigns, Daley did not attend any debates. He believed that a debate would only gift Rush free publicity.
Rush's campaign lacked funding. His campaign's theme was addressing an issue of there being a divide that had created "two Chicagos (similar rhetoric to the notion of a divide creating "Two Americas"). Rush argued that poor neighborhoods had been neglected by Daley, while Daley instead focused on downtown projects such as adding flowerpots to beautify downtown streets and the construction of a ferris wheel at Navy Pier.
Daley won a landslide re-election to an additional term, which (so long as he completed the full term) would make him the second-longest-serving mayor in the city's history behind only his own father (Richard J. Daley), and surpassing Edward Joseph Kelly.
The Chicago Tribune considered Daley's win a significant landslide victory, writing,
Daley received his highest-yet percentage of the vote, slightly surpassing the share he received in 1991. However it was not an all-time record, as several earlier mayors had received higher vote-shares.
Daley won a majority of the vote in 33 of the city's 50 wards. Rush won a majority of the vote in the remaining 17 wards.
The Chicago Tribune observed that Daley had,
This was the last of Daley's campaigns in which he did not carry a plurality of the vote in all 50 wards (as he would do in the next two mayoral elections).
Results by ward<br />
On the evening of the election, Daley delivered a brief victory speech in which he touted his victory as, "a tremendous vote of confidence...built with votes from all of Chicago's neighborhoods," remarking,
In his speech, Daley further remarked on his victory,
The speech was the first of his campaign in which he mentioned Rush by name. Daley promised to collaborate with Rush (who would continue to Represent portions of Chicago in the U.S. House of Representatives) and other elected officials, "for the betterment of our city and all our neighborhoods."
On the evening of the election, Rush delivered a concession speech to a gathering of approximately 200 supporters at the HoneySuckle Chicago Restaurant. He declared that their campaign had "stood tall" in the face of a much better-funded opponent. While conceding the evident outcome of the election, Rush remarked,
Rush expressed no regret in challenging Daley, opining that he believed that it would have been "disingenuous" to have allowed Daley to be re-elected uncontested because there was a need for Daley to face an opponent promoting a movement "fairness and justice" for the entirety of Chicago. Rush remarked,