Cheapest flights to the Caribbean by island and destination

As we are starting a series of articles that will concentrate on Caribbean islands to help winter travelers figure out which is the best for their budget and their style, we thought we d start out by breaking things down by the price of the flights themselves.

It s definitely true that many of the best deals to the Caribbean are part of package holidays where the flight and the hotel (sometimes an all-inclusive hotel) are bundled together into an unbeatable deal. Have a look at our list of the cheapest Caribbean islands and destinations to see where your travel money goes furthest. We ll be sorting through those deals in the coming weeks as well, but in the meantime we ll start by ranking each island and destination by the cost of the flight itself, which will also generally translate into the cost of an entire vacation package.

Cheapest flights from New York City in the coming high-season months

In order to keep things fairly simple we are listing only the cheapest price we ve found in the past 7 days (for a future booking) from any of the 3 New York City-area airports. Interestingly, this is the cheapest starting point for many of the destinations due to the size and competition in the market. If you are flying to many of the smaller islands you ll usually have to change planes in Puerto Rico or at least south Florida.

Those coming from cities other than New York will generally have to pay at least a bit more to reach these destinations, although they ll likely rank in more or less the same order. If you are starting at either Miami or Fort Lauderdale you can find cheaper flights into Nassau (Bahamas), San Juan (Puerto Rico), and the US Virgin Islands, but many destinations are actually more expensive. From Atlanta there are a few good deals, but again, most prices are actually higher in spite of the shorter distance (thanks, Delta!).

Lowest airfare for 31 most popular Caribbean islands and destinations

For the budget traveler it works out pretty well that most of the cheapest islands to reach are also the ones loaded with the cheaper resorts, but this isn t always the case. St. Lucia, for example, has many very affordable beach hotels and it s one of the cheapest of all Caribbean islands to vacation on, but due to the longer distance the flights aren t quite so cheap.

Nearly all of the bottom third of the list are smaller islands where you ll have to change planes at least once if not twice to reach them.

Stay tuned for our full Caribbean coverage that will sort out costs at all 31 of these islands and destinations to help find the bargains as well as the best ones to rub elbows with celebrities and others in the 1%.