Chicago is 59% larger than Detroit.
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: 383 km2 calculated
Detroit is the most populous city in the U.S. state of Michigan and the largest city on the United States-Canada border. It is the seat of Wayne County, the most populous county in the state. Wikipedia