Cheap flights from New York to Caribbean Islands from $66

The month of October is, on average, the cheapest month to fly to Caribbean Islands from New York, with most prices found around $216. The month of May is another great option to travel to Caribbean Islands, with average flight prices from New York averaging around $219.

The cheapest day to depart from New York to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $271. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $319. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

According to our data, the cheapest time of day to fly to Caribbean Islands is at noon. momondo users have found flights departing from New York to Caribbean Islands at noon for as low as $268. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the evening because they tend to be around $324. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Newark to San Juan Luis Munoz Marin Intl for the best New York - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $278 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from New York for as low as $252 on momondo.

There are 4 cabin classes available to choose from on New York to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Frontier, Spirit Airlines, and United Airlines are the most popular carriers operating from New York to Caribbean Islands

JetBlue, United Airlines and Delta are the top three most popular airlines that fly to Caribbean Islands from New York according to our data. JetBlue is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 13 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

The number of flights available between New York and Caribbean Islands is 94 per day as of February 2026. The most frequent departure time is 8:00AM, with 46% of daily flights leaving at noon.

The number of flights available between New York and Caribbean Islands is 660 per week as of February 2026. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.