Chicago is 14 times larger than Manila.
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: 42 km2 calculated
Manila is the capital and second largest city of the Philippines. It is one of the sixteen cities which, along with the municipality of Pateros, make up Metro Manila, the National Capital Region, whose overall population is around 12 million. Wikipedia