| Year | Won | Margin | Democratic | Republican | Total |
|---|---|---|---|---|---|
| 2024 | D | 65,399 | 60,550 | 128,001 | |
| 2020 | D | 66,377 | 58,180 | 127,108 | |
| 2016 | R | 52,627 | 54,047 | 112,662 | |
| 2012 | D | 55,052 | 53,900 | 110,425 | |
| 2008 | D | 53,994 | 52,625 | 107,521 | |
| 2004 | R | 38,744 | 52,283 | 91,541 | |
| 2000 | R | 33,578 | 39,684 | 74,585 | |
| 1996 | R | 28,713 | 29,251 | 62,686 | |
| 1992 | R | 23,495 | 28,909 | 61,868 | |
| 1988 | R | 18,828 | 29,738 | 48,855 | |
| 1984 | R | 16,740 | 27,542 | 44,684 | |
| 1980 | R | 17,155 | 17,888 | 36,904 | |
| 1976 | D | 17,651 | 12,851 | 32,157 | |
| 1972 | R | 373 | 990 | 1,409 | |
| 1968 | D | 6,843 | 6,234 | 24,760 | |
| 1964 | D | 691 | 459 | 1,153 | |
| 1960 | D | 2,155 | 1,341 | 3,521 | |
| 1956 | D | 1,871 | 1,521 | 3,609 | |
| 1952 | D | 1,782 | 1,098 | 2,897 | |
| 1948 | D | 857 | 347 | 1,283 | |
| 1944 | D | 924 | 241 | 1,168 | |
| 1940 | D | 920 | 156 | 1,076 | |
| 1936 | D | 823 | 172 | 1,002 | |
| 1932 | D | 597 | 329 | 945 | |
| 1928 | R | 158 | 865 | 1,023 | |
| 1924 | D | 1,281 | 423 | 1,808 | |
| 1920 | D | 1,824 | 813 | 2,672 | |
| 1916 | D | 1,612 | 684 | 2,337 | |
| 1912 | D | 1,089 | 422 | 1,744 | |
| 1908 | D | 879 | 739 | 1,618 | |
| 1904 | D | 1,345 | 977 | 2,334 | |
| 1900 | R | 2,415 | 3,024 | 5,444 | |
| 1896 | R | 2,137 | 3,475 | 5,674 | |
| 1892 | D | 2,587 | 2,452 | 5,136 | |
| 1888 | — | — | — | — | |
| 1884 | — | — | — | — | |
| 1880 | — | — | — | — | |
| 1876 | — | — | — | — |
Chesapeake shifted from reliably Republican margins to a narrow Democratic lean in 2024, reflecting the broader realignment of Hampton Roads suburbs as military families and college-educated voters remake its electorate.
The Democratic margin in Chesapeake city has rarely exceeded seventy-one points in modern history; the Republican margin has rarely exceeded sixty-nine points. 2024 delivered the county to the Democratic candidate by four points.
Chesapeake city's demographics resemble the country more than they resemble most counties. A 55% non-Hispanic-white share, a 9% poverty rate, and a median household income of $95,373 — all within the broad national range. The county's voting pattern over the last decade is most similar to that of Virginia Beach city and Oktibbeha County.
