Toronto is 9.3% larger than Chicago.
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: 665 km2 calculated
Toronto is the most populous city in Canada and the provincial capital of Ontario. It is located in Southern Ontario on the northwestern shore of Lake Ontario. The history of Toronto began in the late 18th century when the British Crown purchased its land from the Mississaugas of the New Credit. Wikipedia