Anchorage, Alaska is 5 times larger than Chesapeake, Virginia.
Area: 4,476 km2 calculated
Anchorage is a unified home rule municipality in the southcentral part of the U.S. state of Alaska. It is the northernmost city in the United States with more than 100,000 residents and the largest community in North America north of the 60th parallel. Wikipedia
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