The mayoral term in Chicago was two years from 1837 through 1907, at which time it was lengthened to four years. Until 1861, municipal elections were held in March. In that year, legislation changed them to April. In 1869, however, election time was changed to November, and terms expiring in April of that year were lengthened.
| William Butler Ogden | 1837-1838 |
| Buckner Stith Morris | 1838-1839 |
| Benjamin Wright Raymond |
1839-1840
1842-1843 |
| Alexander Lloyd | 1840-1841 |
| Francis Cornwall Sherman |
1841-1842
1862-1863
1863-1865 |
| Augustus Garrett |
1843-1844
1845-1846 |
| Alson Sherman | 1844-1845 |
| John Putnam Chapin | 1846-1847 |
| James Curtiss | 1847-1848 |
| James Hutchinson Woodworth |
1848-1849
1849-1850 |
| Walter S. Gurnee | 1851-1853 |
| Charles McNeill Gray | 1853-1854 |
| Isaac Lawrence Milliken | 1854-1855 |
| Levi Day Boone | 1855-1856 |
| Thomas Dyer | 1856-1857 |
| John Wentworth | 1857-1858
1860-1861 |
| John Charles Haines | 1858-1860 |
| Julian Sidney Rumsey | 1861-1862 |
| John Blake Rice | 1865-1869 |
| Roswell B. Mason | 1869-1871 |
| Joseph Medill | 1871-1873 |
| Harvey Doolittle Colvin | 1873-1875 |
| Monroe Heath | 1876-1879 |
| Carter Henry Harrison, Sr. | 1879-1887
1893 (assassinated in office) |
| John A. Roche | 1887-1889 |
| DeWitt Clinton Cregier | 1889-1891 |
| Hempstead Washburne | 1891-1893 |
| George Bell Swift | 1893 mayor pro tem
1895-1897 |
| John Patrick Hopkins | 1893-1895 |
| Carter Henry Harrison, Jr. | 1897-1905
1911-1915 |
| Edward Fitzsimmons Dunne | 1905-1907 |
| Fred A. Busse | 1907-1911 |
| William Hale Thompson | 1915-1923
1927-1931 |
| William Emmett Dever | 1923-1927 |
| Anton Joseph Cermak | 1931-1933 (assassinated in office) |
| Frank J. Corr | March 15, 1933-April 17, 1933 (32 days, acting) |
| Edward Joseph Kelly | April 17, 1933-April 15, 1947 |
| Martin H. Kennelly | 1947-1955 |
| Richard Joseph Daley | April 20, 1955-December 20, 1976 (died in office) |
| Michael Anthony Bilandic | December 28, 1976-April 16, 1979 |
| Jane Margaret Byrne | April 16, 1979-April 29, 1983 |
| Harold Washington | April 29, 1983-November 25, 1987 (died in office) |
| David Duvall Orr | November 25, 1987-December 2, 1987 (8 days, interim) |
| Eugene Sawyer | December 2, 1987-April 24, 1989 (acting, elected by City Council) |
| Richard Michael Daley | April 24, 1989-present |
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