Find cheap flights from New York to Caribbean Islands – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Best Caribbean Islands Flight Deals from New York

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta CanadirectC$ 508
Montego Bay
Montego Bay1 stopC$ 476
Kingston
Kingston1 stopC$ 663
Port of Spain
Port of SpaindirectC$ 673
Santo Domingo
Santo Domingo1 stopC$ 518
Punta Cana
Punta CanadirectC$ 508
Montego Bay
Montego Bay1 stopC$ 476
Kingston
Kingston1 stopC$ 663
Port of Spain
Port of SpaindirectC$ 673
Santo Domingo
Santo Domingo1 stopC$ 518
Booking Insights

KAYAK's insights & trends for New York to Caribbean Islands flights

Get data-powered insights and trends into flights from New York to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New York John F Kennedy Intl Airport to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from New York John F Kennedy Intl Airport found in the last 5 days was to San Juan, at C$ 350 round-trip. The most popular route is from New York John F Kennedy Intl Airport (JFK) to Nassau (NAS), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 553.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost C$ 668 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 668.

Can I save money by flying with a layover from New York John F Kennedy Intl Airport to Caribbean Islands?

No, with an average price for the route of C$ 989, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from New York John F Kennedy Intl Airport to Caribbean Islands?

The cheapest month for flights from New York John F Kennedy Intl Airport to Caribbean Islands is January, when tickets cost C$ 634 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is C$ 936 and C$ 887 respectively.

How far in advance should I book a flight from New York John F Kennedy Intl Airport to Caribbean Islands?

To get a below-average price on a flight from New York John F Kennedy Intl Airport to Caribbean Islands, you should book around 5 weeks before departure, which saves you about 3% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

September
Best time to beat the crowds (2% less expensive on average)
Most popular time to fly (14% more expensive on average)

Flights from New York to Caribbean Islands: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from New York to Caribbean Islands 
NicoleFlew with Delta-Jun 2026
Terminal has great options for food. Lots of seating and charging stations. If checking luggage and already paid online just drop them at the curbside and continue to the check point.
Maria AlejandraFlew with Frontier-Aug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from New York to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from New York to Caribbean Islands is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New York to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from New York to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from New York to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from New York to Caribbean Islands

 
Need help choosing which airline to fly with from New York to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8700 reviews
8.1Boarding
7.8Comfort
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

Only flew a short distance from Buffalo to New York City JFK SO it was okay

8.0 ExcellentJohn, Oct 2026
Read more Delta reviews

Only flew a short distance from Buffalo to New York City JFK SO it was okay

Delta seems to be getting worse. They are trying to take any comfort away from poorer people to make more money selling it to the rich. I paid for delta comfort and on my flight from Rome to jfk I had a tv that would go on and off automatically and literally no electrical outlets or usbs worked which was advertised in the price of the fare. The infotainment system wasn’t fully working. Luckily the movies worked and the plane was needing a lot of repairs. The jfk to Tampa flight they stuck me next to this really larger guy who was half in my seat and they should have made other accommodations for him because now you’re interfering with the fare class I paid for and act like I shouldn’t care because I didn’t pay for first class. I couldn’t even pull out my tray table because of this guy. The safety video tv screen you couldn’t even see it. It made me a little scared to fly delta anymore, because if these planes are this much in need of servicing, I have to wonder if the plane is going to make it to the destination.

First, off the bat, the Delta gate attendant was rude, inattentive and gave us an attitude when we asked for clarification of our seats for this rebooked flight as we missed our connecting flight due to the delay from Berlin. Flight attendants were all but friendly, rushed through for water refills so you couldn’t even catch them to request more water. Snacks were just OK. Headphones for the movies were so bad that with the airplane noise, the volume of the movie wouldn’t go up enough to even understand the voices. I had to turn on CC to even know what was being said.

Very crowded and the economy seats were the smallest and with the least legroom I have ever experienced. Cabin staff were excellent although the food service was chaotic as they were being each person their food individually instead of from the wagon.

great! appreciated the last minute upgrade to Comfort+ exit row, as well

The crew were very respectful. And also they were welcoming.they did help us locate our seats.i enjoyed.

The wait in the tunnel to enter the plane was too long. The counter personnel, specially ''Israel'' was really not welcoming considering Delta Standards. Other than this everything was good overall.

Delta exceeded my expectations! I am beyond satisfied. Thank you!

Everything was very good or excellent, but the seats were extremely uncomfortable and painful.

We were delayed 2 hours because of a broken seat. Other than that it was a very nice flight.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

Flight was fine, but I was annoyed to have to pay for luggage again. We had paid for our luggage on our first two connecting flights with SATA Azores Airlines, but had to pay for luggage again with JetBlue at JFK airport. For one trip we paid over $500 for two suitcases to travel from Azores to San Francisco.

Uncomfortable seat. No help for my disability. Staff refused to help me put my carry-on in the overhead bin. So I had to check the bag.

Terrible. Quality has gone down significantly. Plane was delayed. No instructions from the staff. Will try to avoid in the future!

The plane was filthy and worn - the seat pockets were stuffed with tattered food and torn pamphlets. The cleaning crew that came on as we were deboarding were grabbing handfulls of trash and perfunctorily wiping down tables with dishrags. It's been a while since I flew Jetblue and it used to be a great experience. After this flight I will avoid flying Jetblue again if there is any alternative.

JFK is the worst airport and JetBlue is the worst airline

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental