Chesapeake, Virginia is 3.1 times larger than Orlando, Florida.
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: 295 km2 calculated
Orlando is a major city in the U.S. state of Florida. Located in Central Florida, it is the county seat of Orange County and the center of the Greater Orlando metropolitan area. Wikipedia