Chesapeake, Virginia is 2.6 times larger than Winston-Salem, North Carolina.
Area: 901 km2 calculated
Chesapeake is an independent city located in the U.S. state of Virginia. As of the 2010 census, the population was 222,209, in 2013, the population was estimated to be 232,977, making it the third-most populous city in Virginia. Chesapeake is included in the Hampton Roads metropolitan area. Wikipedia
Area: 348 km2 calculated
Winston-Salem is a city in and the county seat of Forsyth County, North Carolina, United States. With a 2013 estimated population of 236,441, it is the second largest municipality in the Piedmont Triad region and the fourth largest city in the state. Wikipedia