Chicago is 2.1 times larger than Orlando, Florida.
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: 295 km2 calculated
Orlando is a major city in the U.S. state of Florida. Located in Central Florida, it is the county seat of Orange County and the center of the Greater Orlando metropolitan area. Wikipedia