Cheapest flights to the Caribbean by island and destination

Caribbean vacations can range from cheap to unbelievably expensive, depending on your budget and your ability to find the best deal for your preferences. For most people the two main components of the cost of a trip will be the hotel once you get there and the airfare itself. If you are looking for a cheap Caribbean vacation it’s important to choose a destination that fits your budget for both parts. The list below should help a lot and show which of the islands and destinations have cheap flights and which are actually very expensive to reach.

The list below shows the Caribbean islands and destinations based on the cheapest flight from the New York area in January of 2024 and the list would be similar for any month of the year. We also have lists of the cheapest Caribbean islands for beach hotels and a separate list of cheapest Caribbean islands for all-inclusive resorts.

Fortunately most of the cheaper Caribbean islands are also the larger ones with the most flights and cheaper flights as well. Another thing to consider is a cruise and we also have a handy list of the cheapest Caribbean cruise lines.

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

The list below shows the cheapest price of a flight for a 7-day stay in January, 2024 leaving from one of the New York City or Newark airports. Due to the high demand, flights from NYC are often cheaper even than those leaving from Atlanta or Charlotte, even though those cities are much closer to the Caribbean.

We could run this test for every week of the year and the list would end up being basically in the same order. The larger islands have more flights each week so the airlines can have multiple flights each day during the high season (December through March).

Some of the smaller islands are harder and more expensive to reach in low season (September through November) because flights can be seasonal, but not many people go to those islands in those months anyway.

Lowest airfare for 28 most popular Caribbean islands and destinations

Fares below are the cheapest 7-day roundtrip from New York to each island in January, 2024. Christmas week flights are probably going to be more expensive.

Those looking for an affordable Caribbean vacation will be happy to see that most of the cheaper islands for hotels and resorts are also the cheaper ones for airfare from the US and Canada as well. There are a few exceptions though so you have to be careful before booking a cheap flight only to find that all of the decent beach resorts there are out of your price range.

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. In many cases you have to change planes in San Juan, Puerto Rico, but the smallest islands can also require a change in St. Maarten or another airport in that area.

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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