Thinking about heading to the Caribbean in October or November before high-season resort prices kick in? Well, if you live in the Tri-State area, you can you can save even more money by booking one of the cheapest airfares to the Caribbean from New York. We checked nonstop flights to 10 popular Caribbean destinations and here are the airlines, dates and flight times that are the cheapest. (Note: The best deals — most under $400 and some as low as $239 — are primarily in October and early November for stays of five to seven nights).