Richard M. Daley: With 22 years on the job, the city's longest-serving mayor. A technician and builder with deep political roots. Gave the city its modern look. Son of Richard J. Daley.
Harold Washington: The first African-American mayor, who served from 1983 to 1987 and died in office. Election set the stage for brutal racial political battles dubbed the "council wars."
Jane Byrne: The first woman mayor, ruling from 1979 to 1983. Never consolidated power and never able to deal with machine Democrats.
Richard J. Daley: The last of the big city bosses. Reigned supreme for 21 years after election in 1955. Wielded power by controlling the mechanics of the Democratic Party and the city.
Anton Cermak: In office for three years (1931-33) before being slain at a political appearance in Miami with Franklin D. Roosevelt (who may have been the intended target). Father of the modern Chicago machine. Ended the reign of the "lace curtain" Irish by reaching out to all ethnic groups, including blacks.
William "Big Bill" Thompson: The last Republican to serve (1915-23 and 1927-31) and perhaps the most corrupt mayor on record. Let gangster Al Capone flourish on his watch. Set the stage for Mr. Cermak's Democratic push for reform.
Carter Harrison Sr.: Most beloved of Chicago's early mayors. Called the city his "bride." Elected a total of five times, beginning in 1875. Murdered in 1893 by a disgruntled office seeker.
Joseph Medill: Ran as the "Fireproof" party candidate and served for two years after the "great fire" of 1871. Left office early because of declining health. Helped form the Republican Party and elect Abraham Lincoln president.