New York City is 29% larger than Chicago.
Area: 784 km2 calculated
New York is the most populous city in the United States and the center of the New York metropolitan area, the premier gateway for legal immigration to the United States and one of the most populous urban agglomerations in the world. Wikipedia
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