There’s a nice deal to New York from Winnipeg on at the moment through United (and partner Air Canada). Even with the dollar a bit lower these days, there’s quite a few date combinations can get you there and back this fall for under $400 CAD. Availability appears to be starting now through mid-December, see United.com, Kayak (flex month) or Google Flights to book.
EDIT — November 30: A few dates in December and January are now even lower, down to $358 return on Delta.
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