How many miles is it from Toronto to Chicago?
Approximately 800 miles in straight line distance.
The total distance from Chicago, IL to Toronto, Canada is 437 miles.
Chicago, at 2,695,598 residents is only slightly larger then Toronto at 2,503,281 in population, however Chicago's Metropolitan population is about 4.3 million residents greater then Toronto. Toronto's Metropolitan area covers 2,751 square miles and Chicago's metropolitan area is 10,874 square miles.