Leave and return to Canada from the US and stopover in the US
Upvote:2
This should not be a problem.
While visting Canada does not reset the clock on a VWP visit to the US, if you reside in Canada it does. Each of your visits to the US will treated separately. Telling the immigration official each time you enter that you are studying in Canada should be enough. Having some evidence of that fact would be a good idea, but a record of only entering the US occasionally also means they won't be concerned.
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Source: stackoverflow.com
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