Singapore is 15% larger than Chicago.
Area: 697 km2 World Factbook
Population: 5,567,301 (July 2014) World Factbook
Singapore, officially the Republic of Singapore, is a sovereign city-state and island country in Southeast Asia. It lies off the southern tip of the Malay Peninsula and is 137 kilometres north of the equator. 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