Forty-six men and two women (Jane Byrne, 1979–1983, and Lori Lightfoot, 2019–2023), have held the office.

As an interim mayor, David Duvall Orr (1987) held the office for one week, the shortest time period.

Brandon Johnson (2023–present) is the fourth African American mayor, Eugene Sawyer (1987–1989) having been selected by the council after Washington died in office.

Under Richard M. Daley, the Illinois legislature granted the mayor power to appoint the governing board and chief executive officer of the Chicago Public Schools and subordinated the district to the mayor; the district had long been an independent unit of government.

In practice, however, the mayor of Chicago has long been one of the most powerful municipal chief executives in the nation.

A run-off election, in case no candidate garners more than fifty percent of the vote, is held on the first Tuesday in April.

Chicago is the largest city in the United States not to limit the term of service for its mayor.

A 1995 Illinois law stipulated that "candidates for mayor ... no longer would run under party labels in Chicago".

However, Richard M. Daley, Rahm Emanuel, Lori Lightfoot, and Brandon Johnson are known to be Democrats.

The position was created by a state law that was passed in response to the power struggle that took place over succession following Richard J. Daley's death in office.

[17][18][19] However, in 2023, Mayor Brandon Johnson successfully championed a resolution that gave the office a $400,000 budget.