Chicago is 65% larger than Philadelphia.
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: 370 km2 calculated
Philadelphia is the largest city in the Commonwealth of Pennsylvania, the fifth-most-populous city in the United States, and the core of the sixth-largest metropolitan area in the country. Wikipedia