Chicago is 304 times larger than Monaco.
Area: 2 km2 World Factbook
Population: 30,508 (July 2014) World Factbook
Monaco, officially the Principality of Monaco, is a sovereign city-state and microstate, located on the French Riviera in Western Europe. It is bordered by France on three sides; one side borders the Mediterranean Sea. 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