Chicago is 2.6 times larger than Des Moines, Iowa.
Area: 608 km2 calculated
Chicago is the third most populous city in the United States, after New York City and Los Angeles. With 2.7 million residents, it is the most populous city in both the U.S. state of Illinois and the American Midwest. Wikipedia
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