Missouri (USA) is 293 times larger than Chicago.
Missouri is a U.S. state located in the Midwestern United States. Missouri is the 21st most extensive and the 18th most populous of the 50 United States. Missouri comprises 114 counties and the independent city of St. Louis. The four largest urban areas are St. 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