Des Moines, Iowa is 4 times larger than Manhattan (NYC borough).
Area: 235 km2 calculated
Des Moines is the capital and the most populous city in the U.S. state of Iowa. It is also the county seat of Polk County. A small portion of the city extends into Warren County. It was incorporated on September 22, 1851, as Fort Des Moines which was shortened to "Des Moines" in 1857. Wikipedia
Area: 59 km2 calculated
Manhattan is the most densely populated of the five boroughs of New York City. The borough is coterminous with New York County, an original county of the U.S. state of New York. Wikipedia