Elections are currently held every four years to elect the mayor of Chesapeake, Virginia.
The 2004 Chesapeake mayoral election was held on May 4, 2004. It saw the reelection of the incumbent mayor William E. Ward.
The 2008 Chesapeake mayoral election was held on May 6, 2008. It saw the election of Alan Krasnoff, a member of the city council.
The 2012 Chesapeake mayoral election was held on May 1, 2012. The incumbent mayor Alan Krasnoff won a second term to his mayoral office.
The 2016 Chesapeake mayoral election was held on May 3, 2016. The incumbent mayor Alan Krasnoff won by default due to the lack of opposing candidates.
On the municipal election of Chesapeake in November 2017, the incumbent mayor Alan Krasnoff ran for and won the election was the Chesapeake City Clerk of Court. Since Krasnoff left the post of mayor on November 14, Richard West, a city council member, became the acting mayor. A special mayoral election was held on May 1, 2018. It saw the election of the acting mayor Richard West.
The 2020 Chesapeake mayoral election was held on May 19, 2020. It saw the reelection of the incumbent mayor Richard West.
The following served as mayors of Chesapeake: