JFK - PVG - YYZ

My boss will be flying from New York City to Shanghai on Wednesday, May 30th. On Friday, June 1st he will fly from Shanghai to Toronto. This is being done merely as a way to avoid getting him a business visa, I'll have to get him from YYZ back to NYC if this works.

Does this work? Toronto and New York City are in different countries, but the same "region" so looking for confirmation here.

Thanks!