Cheapest flights to the Caribbean by island and destination

As we now have a series of articles that concentrate on several of the 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 certainly true that many of the best deals to the Caribbean are part of package holidays where the flight and the hotel (sometimes an luxury all-inclusive resort) 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. Also consider looking into your choices for the cheapest Caribbean cruise, as those can also be great bargains.

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

In order to keep things fairly simple and easy to understand we are listing only the cheapest price we’ve found in the past 7 days in March 2020 (for a future booking in 2020) from any of the 3 New York City-area airports. The prices below are for one person. Interestingly and perhaps a bit surprising, this is the cheapest starting point for many of the destinations listed below due to the size and competition within the flight 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 in 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. When traveling from Atlanta you’ll find that 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%.

Photo courtesy of michael feagans on Flickr

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  1. Snowskidude says:

    This peers to be a great list of inexpensive flights to the Caribbean… but it was posted back in November 2011.
    Does anyone know of an updated list for 2015?

    1. Roger Wade says:


      Our most recent Caribbean airfare tests appear on this main page about the cheapest Caribbean islands from early 2015. It’s similar in that we found the best fares to each island from New York City. And even if you are starting from another city, the rankings of islands by airfare should be similar. I hope this helps. -Roger

  2. Gina says:

    Hi Roger,

    A bunch of my friends and I are going to the Bahamas from 6/17-6/21. Right now the flights are looking at $485 RT from San Francisco. Is this considered a good deal or should I wait a little longer before I book the flight.


    1. Roger Wade says:


      Interestingly, I got a nearly identical question from someone named Jay just a bit ago. My response is at the bottom of the comments on this other article about when is the best time to buy plane tickets. Best of luck with it and have a great trip. -Roger

  3. cassandra todmann says:

    how to fly from sju to aruba without coming to usa

    1. Roger Wade says:


      Technically, San Juan (SJU) is in the USA already. But if you want to change planes in a third country you can fly on Copa Airlines changing in Panama City, Panama. Have a great trip. -Roger