$70 Find Cheap Flights from New York to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to Caribbean Islands departing on 1/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Caribbean Islands.
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Flight Deals

Cheap Flights from New York to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$276
Santo Domingo
Santo Domingo1 stop$283
Montego Bay
Montego Baynonstop$318
Oranjestad
Oranjestad2 stops$295
Nassau
Nassau2 stops$308
Kingston
Kingston1 stop$340
Simpson Bay
Simpson Bay1 stop$261
Providenciales
Providenciales1 stop$288
Port of Spain
Port of Spain1 stop$293
Bridgetown
Bridgetownnonstop$328
George Town
George Town1 stop$257
Willemstad
Willemstad1 stop$234
Castries
Castries2 stops$450
St. John's
St. John'snonstop$306
Puerto Plata
Puerto Platanonstop$325
Aguadilla
Aguadillanonstop$229
Punta Cana
Punta Cana1 stop$276
Santo Domingo
Santo Domingo1 stop$283
Montego Bay
Montego Baynonstop$318
Oranjestad
Oranjestad2 stops$295
Nassau
Nassau2 stops$308
Kingston
Kingston1 stop$340
Simpson Bay
Simpson Bay1 stop$261
Providenciales
Providenciales1 stop$288
Port of Spain
Port of Spain1 stop$293
Bridgetown
Bridgetownnonstop$328
George Town
George Town1 stop$257
Willemstad
Willemstad1 stop$234
Castries
Castries2 stops$450
St. John's
St. John'snonstop$306
Puerto Plata
Puerto Platanonstop$325
Aguadilla
Aguadillanonstop$229

Book Cheap New York to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New York to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New York to Caribbean Islands

Mon, Jan 26 - Fri, Jan 30
Frontier Logo
1:00 pm - 5:58 pm
JFK
-
SJU
3h 58mnonstop
Frontier Logo
8:50 am - 12:04 pm
SJU
-
JFK
4h 14mnonstop
$139Frontier
Sat, Jan 31 - Wed, Feb 4
Spirit Airlines Logo
7:30 am - 6:49 pm
LGA
-
SJU
10h 19m1 stop
Spirit Airlines Logo
4:40 pm - 11:48 pm
SJU
-
LGA
8h 08m1 stop
$139Spirit Airlines
Thu, Jan 29 - Thu, Feb 5
United Airlines Logo
6:00 am - 5:25 pm
EWR
-
PUJ
10h 25m1 stop
United Airlines Logo
12:56 pm - 7:10 pm
PUJ
-
EWR
7h 14m1 stop
$279United Airlines
Thu, Jan 29 - Tue, Feb 3
American Airlines Logo
2:44 pm - 4:33 pm
JFK
-
PUJ
24h 49m1 stop
American Airlines Logo
12:54 pm - 4:03 pm
PUJ
-
JFK
4h 09mnonstop
$280American Airlines
Thu, Feb 19 - Thu, Feb 26
American Airlines Logo
5:26 pm - 3:55 pm
JFK
-
PUJ
21h 29m1 stop
American Airlines Logo
12:57 pm - 4:05 pm
PUJ
-
JFK
4h 08mnonstop
$281American Airlines
Mon, Jan 19 - Fri, Jan 23
United Airlines Logo
6:52 am - 11:50 am
EWR
-
PUJ
3h 58mnonstop
United Airlines Logo
5:20 pm - 11:59 pm
PUJ
-
EWR
7h 39m1 stop
$284United Airlines
Sat, Jan 31 - Tue, Feb 3
JetBlue Logo
2:10 pm - 7:07 pm
JFK
-
PUJ
3h 57mnonstop
JetBlue Logo
4:45 pm - 7:55 pm
PUJ
-
JFK
4h 10mnonstop
$289JetBlue
Fri, Feb 6 - Sun, Feb 8
JetBlue Logo
9:45 am - 3:30 pm
JFK
-
AUA
4h 45mnonstop
JetBlue Logo
6:00 pm - 9:52 pm
AUA
-
JFK
4h 52mnonstop
$296JetBlue
Mon, Jan 19 - Wed, Jan 28
Delta Logo
6:00 am - 3:20 pm
EWR
-
AUA
8h 20m1 stop
Delta Logo
2:10 pm - 9:00 pm
AUA
-
EWR
7h 50m1 stop
$302Delta
Tue, Feb 24 - Thu, Mar 5
Delta Logo
7:30 pm - 12:32 am
JFK
-
SDQ
4h 02mnonstop
Delta Logo
2:35 pm - 5:50 pm
SDQ
-
JFK
4h 15mnonstop
$320Delta
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 to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from New York found in the last 72 hours was to San Juan, at $105 round-trip. The most popular route is from New York John F Kennedy Intl Airport (JFK) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $112.

Can I save money by flying with a layover from New York to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $505, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from New York to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New York to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from New York to Caribbean Islands is March, when tickets cost $207 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $361 and $356 respectively.

What’s the cheapest day of the week to fly from New York to Caribbean Islands?

The average price of all round-trip flights from New York to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from New York to Caribbean Islands. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

How far in advance should I book a flight from New York to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from New York to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from New York to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$70
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from New York LaGuardia Airport to San Juan Airport

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

Insights shared by verified travelers who flew the route from New York to Caribbean Islands 
Maria AlejandraFlew with Frontier
JFK
-
SJU
Aug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
Verified travelerFlew with United Airlines
EWR
-
SDQ
Apr 2024
Early check in online, get on time for the flight

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 travelers 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.

  • 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 afternoon, when round-trip flights cost $234 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $319.

Reviews of the top 5 airlines serving from New York to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from New York to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.9
Caribbean AirlinesOverall score based on 211 reviews
6.7Food
6.6Entertainment
8.3Crew
7.8Comfort
8.0Boarding
Airline reviews

There was no flight. They canceled the flight with no knowledge to me, and I still haven’t received a refund

2.0 Mediocrejahbless, Dec 2025
FLL - KIN
Read more Caribbean Airlines reviews

There was no flight. They canceled the flight with no knowledge to me, and I still haven’t received a refund

Overall, it was good. There was no food or entertainment, which is why I put poor (it wasn't an issue though).

Nothing, they could have made some accommodation for an awful experience. Me and my family were not informed properly we we separated. They took me off the original flight i booked. I booked our flight at one price and called me and told me they were not honoring my rate and they charged me double of what I paid. Me and my family don’t want to ever use your services again.

This flight was great. The plane took off and arrived at the destination an hour early. The crew was pleasant. The food and entertainment options are minimal but adequate for a 1-hour flight. They passed out water and quickly supplied me with a fresh magazine since the previous one had the crossword section filled out.

Better movie and tv selections. Also, the overnight flight to Trinidad from Toronto, the staff were not very attentive. I did not see them for at least half the fight. They were behind their curtain a lot of the time, and they did not check on us before landing to make sure all landing requirements were met.

Little space for luggage and the flight was delayed by an hour.

The flight was delayed over a hour and that was over 15 hours in advance not good

At check in I had to pay for my seat that I already paid for on purchasing my ticket. The flight was over an hour late and the plane smelt gross.

just a child who screamed and threw tantrums the entire flight

Excellent experience this was my first time booking with Kayak.

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

I truly love flying with Delta. They have always treated me with the upmost respect

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight was great. The gate location was way to far away!!!

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

Aircraft was noisy, old and never dimmed the lights on a night flight even on business class! I flew 17 times on United and probably another 40 on other airlines United USA /Europe flights were the worst to include luggage delayed once going to europe and once coming back

Check how old the airframe is, some older ones have inoperable seat back entertainment or power.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

Flight and crew were great. United didn't inform crew of immigration process which was disappointing!

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

Friendly and professional flight crew. Aside from departure delay after boarding, easy flight and smooth landing.

Flight was timely, relatively comfortable, with decent entertainment and food served. Only problem encountered was with the free messaging which I highly appreciate, but it did not work from iphone to non-iphones.

Food was poorly timed and not good.. Hand held snacks, really. I kept asking for water and never got any. Service was rushed for a 7-hour flight.

Boarding was organized. Old plane. Seat fairly comfortable. Business Class much too large so you don’t receive as much attention as you should considering what you pay for the seat.

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

Disliked having to wait a little longer to disembark from the plan when we landed in London

Food should be better quality. Video screens have poor resolution and the library of movies is poor. The other airlines are much better.

They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

We arrived 4 hours early and still almost missed the flight because they weren’t able to access one of the boarding tickets. They then sent hour bags late and we were all of our without clothing and eventually had to take an expensive cab back and forth to the airport as they wouldn’t deliver the bag which arrived late at night that day and we would have to wait until noon the began day (messing up a second day of plans). Also, all the food has dairy or pork. No vegan or even vegetarian option in the flight—even for purchase.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

Pathetic check in experience at JFK. Everything is self check in. Not enough staff present to help with when the check in process or the kiosk gets stuck. Staff present not welcoming or pleasant at all. On the other hand the NY based flight crew was great. Courteous and friendly throughout the flight. Special meals leave a lot to be desired. Kids meals should be made available when kids are flying and same goes for special kids meals too.

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

Not a pleasant experience, service was poor. Didn't like it

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

The flight departed more than 1 hour late. Leg room is bigger than most airlines

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to New York

Cabin classes available on flights to New York. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.