$61 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 10/12. 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

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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Flights Deals

Best Caribbean Islands Flight Deals from New York

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$260
Santo Domingo
Santo Domingononstop$228
Montego Bay
Montego Bay1 stop$260
Oranjestad
Oranjestadnonstop$280
Nassau
Nassaunonstop$308
Kingston
Kingston1 stop$291
Simpson Bay
Simpson Bay1 stop$252
Providenciales
Providencialesnonstop$328
Port of Spain
Port of Spain2 stops$332
Bridgetown
Bridgetown2 stops$323
George Town
George Town1 stop$329
Willemstad
Willemstad1 stop$367
Castries
Castries2 stops$466
St. John's
St. John's1 stop$264
Puerto Plata
Puerto Platanonstop$340
Aguadilla
Aguadilla1 stop$230
Punta Cana
Punta Cananonstop$260
Santo Domingo
Santo Domingononstop$228
Montego Bay
Montego Bay1 stop$260
Oranjestad
Oranjestadnonstop$280
Nassau
Nassaunonstop$308
Kingston
Kingston1 stop$291
Simpson Bay
Simpson Bay1 stop$252
Providenciales
Providencialesnonstop$328
Port of Spain
Port of Spain2 stops$332
Bridgetown
Bridgetown2 stops$323
George Town
George Town1 stop$329
Willemstad
Willemstad1 stop$367
Castries
Castries2 stops$466
St. John's
St. John's1 stop$264
Puerto Plata
Puerto Platanonstop$340
Aguadilla
Aguadilla1 stop$230

Cheap Flights from New York to Caribbean Islands

 
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

Tue, Sep 9 - Fri, Sep 12
Frontier Logo
6:00 am - 9:56 amJFK-SJU
3h 56mnonstop
Frontier Logo
9:26 pm - 1:25 amSJU-JFK
3h 59mnonstop
$134Frontier
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Sun, Oct 5 - Sat, Oct 18
JetBlue Logo
6:59 am - 10:54 amEWR-SJU
3h 55mnonstop
JetBlue Logo
3:55 pm - 8:03 pmSJU-EWR
4h 08mnonstop
$136JetBlue
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Tue, Aug 5 - Fri, Aug 15
Spirit Airlines Logo
7:00 pm - 11:32 amEWR-SJU
16h 32m1 stop
Spirit Airlines Logo
4:12 pm - 8:57 amSJU-EWR
16h 45m1 stop
$139Spirit Airlines
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Tue, Sep 9 - Fri, Sep 12
American Airlines Logo
6:33 am - 3:52 pmJFK-SJU
9h 19m1 stop
American Airlines Logo
4:43 pm - 10:38 amSJU-JFK
17h 55m1 stop
$145American Airlines
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Tue, Sep 9 - Fri, Sep 12
American Airlines Logo
9:00 am - 3:52 pmLGA-SJU
6h 52m1 stop
American Airlines Logo
4:43 pm - 11:45 pmSJU-LGA
7h 02m1 stop
$145American Airlines
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Tue, Aug 5 - Fri, Aug 8
Spirit Airlines Logo
5:45 am - 3:30 pmEWR-SJU
9h 45m1 stop
Spirit Airlines Logo
11:59 pm - 4:11 amSJU-EWR
4h 12mnonstop
$147Spirit Airlines
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Tue, Nov 4 - Mon, Nov 10
Delta Logo
1:00 pm - 11:21 pmLGA-SJU
9h 21m1 stop
Delta Logo
7:30 am - 5:44 pmSJU-LGA
11h 14m1 stop
$225Delta
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Mon, Sep 1 - Thu, Sep 4
Delta Logo
8:15 am - 12:25 pmJFK-PUJ
4h 10mnonstop
Delta Logo
1:50 pm - 6:07 pmPUJ-JFK
4h 17mnonstop
$260Delta
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Thu, Sep 11 - Mon, Sep 15
United Airlines Logo
6:00 am - 12:40 pmEWR-PUJ
6h 40m1 stop
United Airlines Logo
3:15 pm - 7:24 pmPUJ-EWR
4h 09mnonstop
$265United Airlines
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Fri, Nov 28 - Wed, Dec 3
United Airlines Logo
7:00 am - 5:25 pmEWR-PUJ
9h 25m1 stop
United Airlines Logo
6:32 pm - 9:49 pmPUJ-EWR
4h 17mnonstop
$290United Airlines
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from New York to Caribbean Islands.

The cheapest ticket to Caribbean Islands from New York found in the last 72 hours was to San Juan, at $139 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 $139.

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 $1,293, 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 $196 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $396 and $327 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 4 weeks before departure.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$61
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 37% increase in price.
Flight from Newark Liberty 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 FrontierJFK-SJUAug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
Verified travelerFlew with United AirlinesEWR-SDQApr 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 $207 on average. Morning departures are around 2% cheaper 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 $326.

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.
8.2
Caribbean AirlinesOverall score based on 164 reviews
8.5Crew
8.1Boarding
6.9Food
7.9Comfort
6.8Entertainment
Airline reviews

Flight time. The crew was the rudest, talked down to customers, ignored requests, acted like security guards, used forceful language like must and can't. Everything was on purchase, no entertainment, unless you could use your own phone. Poor customer service.

4.0 OkaySheldon, Jul 2025MIA - POS
Read more Caribbean Airlines reviews

Flight time. The crew was the rudest, talked down to customers, ignored requests, acted like security guards, used forceful language like must and can't. Everything was on purchase, no entertainment, unless you could use your own phone. Poor customer service.

Checking in, boarding, the food and crew were all excellent. It was my first time traveling on Caribbean Airlines and trust me it’s the only airline I’ll be flying on as of now as long as it’s going my way😁. The service was unbelievably good I don’t regret missing my flight on flair at all cause I wouldn’t have realized how great the service is on Caribbean Airlines

The flight could'nt be better ,the comfort ,the crew and everything was good.i will definitely fly with this sirline again.

I love my entire experience. What I love most, was the friendliness and helpfulness of the staff at check-in and that of the crew on the flight. Their Customer Service was paramount.

The flight crew was extremely hospitable, though there was a lot of turbulence, they made it a good experience. The only negative was the inflight experience for economy class. There wasn’t any, or at least non that I was aware of.

I liked the friendliness of the employees at the airport

I liked the extra leg room in Caribbean plus. Worth the extra money. The food could have been more balanced, there was no salad or veggies

The Flight itself was smooth and uneventful. The crew was polite and caring. I used the Lounge in Piarco and the service was STELLAR

Crew were quite friendly. Food was very poor considering the price of the ticket and the flight time. Could not charge my phone due to USB charger not working..

The food wasn’t good. Need better food. There wasn’t any entertainment.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

Overall, aside from the baggage issue, it was as good as one expects.

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Our bag was lost so that made unnecessary chaos On our trip

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The food should improve! And The flight should leave on time and not make the traveler wait.

We love united ! We would like to acknowledge Aimee in the lounge near gate 130

Survey sent before we actually left. Delay after delay. Now a crew problem.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

The flight was operated by Lufthansa. You can't expect much from them anymore. They have a talent in getting something wrong.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Smooth flight, especially take off and landing, and great crew on board. Really loved the stroopwaffles!

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Not really their fault, but a 4.5 hour delay is pretty brutal

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.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

The flight crew that we had in our section may have been tired or something. I asked the flight attendant about my son’s screen not working and she spoke down to me like I was stupid. He still had no working screen throughout his flight. The other members had no personality and seemed like they were annoyed when you asked them for something. Definitely took a hit for simple things on my JB experience.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

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.

Delays on all NY flights. There was no communication on why but they didn’t say it was weather. Other carriers were not delayed.

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

They cancelled our flight without warning OR a refund. Never doing business with American Airlines again! This is the second AA booked trip in a row that we've had challenges with.

I got bumped due to weight restrictions even tho there were empty seats on my flight. I got put on an other flight with a stopover. My flight that originally was going to take 5-6 hours ever up being 14+ hours and my luggage arrived to my destination without me because I was made to check in my luggage on my original flight when I was deemed ok to board only to be asked to deplane. Worst flight experience.

Flight cancelled. Added a day and a half to my travel. American Airlines DID put me in a hotel for two nights, but have not given any money back for any of this! I spent money on an apartment at my destination that I basically wasted because I could not arrive.

I was pleasantly surprised with an upgrade at boarding. I finally had a mostly gluten free food options and a very attentive attendant.

Staff at the gate were incredibly rude, hostile and threatening. Never fly American Airlines.

AA had a nationwide tech glitch today and after two connections snd hours of delay, I arrived 7 hours late to my destination

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.

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