Chicago is 9 times larger than Boulder, Colorado.
Area: 68 km2 calculated
Boulder is the county seat and most populous city of Boulder County and the 11th most populous city in the U.S. state of Colorado. Boulder is located at the base of the foothills of the Rocky Mountains at an elevation of 5,430 feet. The city is 25 miles northwest of Denver. 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