Jacksonville, Florida is 5.7 times larger than Winston-Salem, North Carolina.
Area: 1,988 km2 calculated
Jacksonville is the largest city in the U.S. state of Florida by population and the largest city by area in the contiguous United States. It is the county seat of Duval County, with which the city government consolidated in 1968. 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