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Google Maps estimates the driving time as 13 hours and 47 minutes.

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Q: How long to drive from Ottawa Ontario to Chicago Illinois?
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How far is it to drive to Chicago Illinois from Owen Sound Ontario Canada?

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Depends on what part of Ontario and how fast you plan to drive. Chicago to Windsor (the closest Canadian city to the border. It is basically right beside Detroit) is about a 5 hour drive. To get to the Toronto (Canada's largest city) it would take around 8 hours. To get to Ottawa (Canada's Capital) it would take roughly 13 hours.