It is 863 miles (1,389 miles) taking this route:
722 miles
The driving distance from Winnipeg, Canada to Springfield, Illinois is 980 miles / 1,577 km.
Chicago to Montreal is about 850 miles.
Toronto, Canada, is 437 miles northeast of Chicago, Illinois. That is 703 kilometers or 379 nautical miles.
It is 489 miles according to Google Maps.
The flight distance from Chicago, Illinois to Windsor, Canada is: 240 miles / 386 km
Distance from Chicago to Winnipeg is 1324 miles. Not sure if this is air or road. Web site resource was: http://www.travelmanitoba.com/default.asp?page=53&node=635&menu=436 John :-#)#
Approximately 500 miles.
It is 521 miles according to Google Maps.
The flight distance from Chicago, Illinois to Windsor, Canada is: 240 miles / 386 km
The flight distance from Chicago, Illinois to Ottawa, Canada is: 647 miles / 1,041 km
It is 791 miles according to Google Maps.