Chicago is 8,107,862 times larger than Jackson, Mississippi.
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: 0 km2 calculated
Jackson is the capital and since 1944 the largest city of the U.S. state of Mississippi. Located south of the Yazoo River, it is considered to be at the southern border of the Mississippi Delta and is one of two county seats of Hinds County, with the city of Raymond being the other. Wikipedia