A lawsuit was filed by an anti-Sawyer coalition of black activists and several Harold Washington supporters demanding a special election be held as soon as possible.

[3] On May 5, 1988, Eugene Wachowski, judge of the Cook County Circuit Court, held that a special election would be required to be held in 1989 on the basis of three previous rulings by Circuit, Appellate, and Supreme Court judges and by a 1978 legislative debate from when the Illinois General Assembly passed the then-current election law.

[4][5] Richard M. Daley won the Democratic primary, defeating Eugene Sawyer, who had been appointed mayor by City Council following the death of Harold Washington.

He also faced Sheila A. Jones[6] and James C. Taylor[6][7] (State Senator who had also been chief of staff in Jane Byrne's mayoral administration).

[3] The campaign overspent on media advertising and failed to spend enough on literature, field operations, and lawn signs.

[3] The African-American anti-Sawyer faction, whose members were responsible for the lawsuit that led to the special election being ordered, rallied around Alderman Timothy C. Evans, whom they viewed as the proper heir to Washington's political legacy.

[3] In July 1988, after receiving months of attacks from pro-Evans aldermen, Sawyer retaliated by stripping them of their committee chairmanships in a City Council restructuring.

[11] Bloom had entered the race in September 1988 and had originally started his campaign near the front of the pack, benefiting from what the press referred to as a "squeaky clean" reputation.

[21] During the campaign, Daley and Sawyer avoided lodging personal attacks, and both called for racial harmony.

[22] The poll also found that Jewish and Hispanic voters, who Sawyer had hoped to capture the support of, had strongly went for Daley.

[11] Vrdolyak obliged, launching a last-minute a write-in campaign for the nomination only a week before the late February primary.

[44][45] He defeated the GOP-backed Sohn by more than a thousand votes, which put him out of reach of the 5% spread for a recount to be triggered.