Harrison won a majority of the vote, defeating the Republican nominee, businessman Samuel W. Allerton, by a ten-point margin.

Ahead of the general election, Harrison had faced opposition in his race to receive the Democratic Party's nomination.

Both former mayor Cregier and Illinois Staats-Zeitung newspaper editor and former Cook County deputy sheriff Washington Hesing also sought the Democratic nomination at the party's convention.

[3] In the time since the 1891 election, Harrison had made peace again with the Democratic Party, supporting its 1892 presidential nominee Grover Cleveland.

[3] In addition, Harrison had a longstanding feud with Michael C. McDonald, then an influential figure in Chicago Democratic politics.

[5][6] Three individuals suggested themselves to Democrats as potential contenders: former mayor DeWitt Clinton Cregier, and Washington Hesing.

[3] Harrison entered the race without having the support of significant organized groups or newspapers (other than the Chicago Times, which he owned).

[3] This troubled many establishment Democrats, such as Roger Charles Sullivan and John Patrick Hopkins, who were concerned that the charismatic Harrison would come to dominate the party if he was successful at winning the mayoralty.

[3] Hopkins and his political partner Roger Charles Sullivan looked at several prospective candidates to challenge Harrison for the nomination.

[3] Ultimately, Hopkins settled on Illinois Staats-Zeitung editor and former Cook County deputy sheriff Washington Hesing.

[4] At the convention, held March 1[6] at the Central Music Hall, three candidates had their names put forth for the nomination: Harrison, Hesing, and Cregier.

[7] The Republicans had sought to recruit a top-capitalist figure of the city to face Harrison in the general election, but had failed in their attempts to persuade Philip Danforth Armour or Lyman J. Gage to run.

[9] The city elite largely considered Harrison to be too liberal and believed that he allowed himself to be surrounded by corrupt associates.

Allerton argued that the administration of the upcoming World's Fair presented a model for the business-style governance Chicago should adopt.

[7] He received the backing of the city's business elite, such as Philip Danforth Armour, Lyman J. Gage, Harry Gordon Selfridge, Charles L. Hutchison, Franklin MacVeigh, Harlow Higinbotham, and Turlington Harvey.

[7] Some Christian evangelists even tied blame for the Haymarket affair bombing with Harrison's support for allowing saloons to remain open on Sundays.

[3] Harrison effectively responded to criticisms of his record by stating that he had done the best he could when previously mayor to work around state-imposed limitations on the city's taxation powers.

Meanwhile, Republicans advocated for an unrealistic combination of lower taxes and expanded municipal services, unconvincingly telling voters that needed money could be saved if the city decreased its number of civil servants by having professional appointees fill positions traditionally held by patronage appointees.

However, in this era, mayoral races in Chicago were still typically closely contested, and Republicans usually carried the city in national elections.

The Republican-aligned Chicago Tribune newspaper predicted that such a victory would be facilitated by a strong Republican vote in the city's German ward (where Hesing had been popular), expecting massive defections from the Democratic Party to Republican party by voters in those wards of voters (which typically leaned Democratic).