Chesapeake is an independent city in Virginia, United States. At the 2020 census, the population was 249,422, making it the second-most popu…Chesapeake is an independent city in Virginia, United States. At the 2020 census, the population was 249,422, making it the second-most populous city in Virginia, the tenth largest in the Mid-Atlantic, and the 89th-most populous city in the United States.