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Chicago Mayoral Election Quiz

by Annalee AlbertsonPublished: December 13, 2025

Chicago’s mayoral elections have been a cornerstone of the city’s political landscape, reflecting its diverse and dynamic history. This quiz will challenge your understanding of the pivotal moments, influential candidates, and significant outcomes that have defined Chicago’s leadership. Ready to see how well you know the Windy City’s political past and present? Let’s get started!
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Chicago Mayoral Election Quiz
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1. Who was the first mayor of Chicago?
Hint: He served from 1837 to 1838.

Chicago Mayoral Election Quiz Questions Overview

1. Who was the first mayor of Chicago?

William B. Ogden
John H. Kinzie
Carter Harrison Sr.
Richard J. Daley

2. Which Chicago mayor served the longest term?

Richard J. Daley
Harold Washington
Jane Byrne
Rahm Emanuel

3. Who was the first African American mayor of Chicago?

Harold Washington
Eugene Sawyer
Lori Lightfoot
David Orr

4. Which mayor was the first woman to hold the office in Chicago?

Jane Byrne
Lori Lightfoot
Toni Preckwinkle
Dorothy Tillman

5. Who succeeded Harold Washington after his death in 1987?

Eugene Sawyer
David Orr
Richard M. Daley
Michael Bilandic

6. Which mayor is known for the controversial decision to bulldoze Meigs Field?

Richard M. Daley
Rahm Emanuel
Jane Byrne
Harold Washington

7. Who was the mayor of Chicago during the Great Chicago Fire of 1871?

Roswell B. Mason
Joseph Medill
John Wentworth
Carter Harrison Sr.

8. Which mayor launched the ‘Chicago Plan’ for urban development in the early 20th century?

Carter Harrison Jr.
Fred A. Busse
William Hale Thompson
Edward F. Dunne

9. Who was the mayor of Chicago during the 1968 Democratic National Convention?

Richard J. Daley
Michael Bilandic
Harold Washington
Jane Byrne

10. Which mayor initiated the Millennium Park project?

Richard M. Daley
Rahm Emanuel
Lori Lightfoot
Jane Byrne

11. Who was the first openly gay mayor of Chicago?

Lori Lightfoot
Toni Preckwinkle
Jane Byrne
Rahm Emanuel

12. Which Chicago mayor was known for his efforts to improve public transportation?

Richard M. Daley
Harold Washington
Jane Byrne
Rahm Emanuel

13. Who was the mayor of Chicago when the city hosted the World’s Columbian Exposition in 1893?

Carter Harrison Sr.
John P. Hopkins
George Bell Swift
William E. Dever

14. Which mayor was in office during the Chicago Cubs’ World Series win in 2016?

Rahm Emanuel
Lori Lightfoot
Richard M. Daley
Jane Byrne

15. Who was the mayor of Chicago during the launch of the Chicago Riverwalk project?

Rahm Emanuel
Richard M. Daley
Lori Lightfoot
Jane Byrne
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