Antarctica is 23,023 times larger than Chicago.
Area: 14,000,000 km2 World Factbook
Population: 4,490 (Summer 2009) World Factbook
Antarctica is Earth's southernmost continent, containing the geographic South Pole. It is situated in the Antarctic region of the Southern Hemisphere, almost entirely south of the Antarctic Circle, and is surrounded by the Southern Ocean. 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