Former mayor Jane Byrne (who had held office from 1979 until 1983) unsuccessfully challenged Washington in the Democratic primary.

[5] Four years earlier Washington had won nomination against divided opposition, and in 1987 faced a more united bloc of opponents.

[9] Byrne's campaign ads argued that under Washington's tenure racial tensions in Chicago had increased.

Hynes (a career-long Democrat) opted to make a third party run after leading Republican operatives persuaded him to do so.

[16][17][18] The following individuals received speculation as prospective candidates, but did not run: At one point it was believed that, if a federal bribery investigation against members of City Hall (including some in Washington's administration) had proved damaging enough to Washington, he might face a particularly notable Republican opponent such as former governor Richard B. Ogilvie or former U.S. attorney Dan K. Webb (the latter of whom had been involved in launching the aforementioned bribery probe).

Thompson saw his own position of influence in Illinois politics and enhanced by a discordant local government in Chicago.

[5] 1983 Republican naominee Bernard Epton announced his candidacy in 1986, but his run was not greeted with any excitement from figures in the county party.

[5] The Republican Party nominated Donald Haider, a business professor and former city budget director.

[19] Haider narrowly defeated 1983 nominee Bernard Epton for the Cook County Republican Party's endorsement.

Vrdolyak formally received the Illinois Solidarity nomination in the party's primary, held on February 24.

[30] "Chicago First" nominee Thomas Hynes withdrew two days before the election and threw his support behind Washington's two remaining opponents.

[31][32] Some regarded Washington's modest margin of victory in the Democratic primary as an indicator that he would be vulnerable in the general election.

He claimed he was a fresh alternative to the dirty infighting that had defined Chicago politics in recent years.

[34] Just two days before the general election, Hynes dropped out, leaving Vrdolyak and Haider as Washington's remaining opponents.

Hynes did not throw his support to any of the remaining candidates, but suggested that either Vrdolyak or Haider should also drop out make it a one-on-one race against Washington.