Anchorage, Alaska is 7.4 times larger than Chicago.
Area: 4,476 km2 calculated
Anchorage is a unified home rule municipality in the southcentral part of the U.S. state of Alaska. It is the northernmost city in the United States with more than 100,000 residents and the largest community in North America north of the 60th parallel. 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