$92 Find Cheap Flights from New York to Caribbean Islands - Compare and Save

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 9/23. 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.
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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$431
Santo Domingo
Santo Domingononstop$274
Montego Bay
Montego Baynonstop$396
Oranjestad
Oranjestadnonstop$371
Nassau
Nassaunonstop$312
Kingston
Kingston1 stop$337
Simpson Bay
Simpson Bay1 stop$373
Providenciales
Providenciales1 stop$375
Port of Spain
Port of Spainnonstop$405
Bridgetown
Bridgetown2 stops$457
George Town
George Townnonstop$393
Willemstad
Willemstad2 stops$237
Castries
Castries1 stop$495
Aguadilla
Aguadillanonstop$285
Puerto Plata
Puerto Platanonstop$515
St. John's
St. John'snonstop$386
Punta Cana
Punta Cana1 stop$431
Santo Domingo
Santo Domingononstop$274
Montego Bay
Montego Baynonstop$396
Oranjestad
Oranjestadnonstop$371
Nassau
Nassaunonstop$312
Kingston
Kingston1 stop$337
Simpson Bay
Simpson Bay1 stop$373
Providenciales
Providenciales1 stop$375
Port of Spain
Port of Spainnonstop$405
Bridgetown
Bridgetown2 stops$457
George Town
George Townnonstop$393
Willemstad
Willemstad2 stops$237
Castries
Castries1 stop$495
Aguadilla
Aguadillanonstop$285
Puerto Plata
Puerto Platanonstop$515
St. John's
St. John'snonstop$386

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

Wed, Sep 16 - Sat, Sep 19
American Airlines Logo
6:30 am - 2:50 pm
JFK
-
SJU
8h 20m
1 stop
American Airlines Logo
10:16 am - 7:24 pm
SJU
-
JFK
9h 08m
1 stop
$281American Airlines
Wed, Sep 9 - Mon, Sep 14
American Airlines Logo
7:59 am - 3:40 pm
LGA
-
SJU
7h 41m
1 stop
American Airlines Logo
10:16 am - 6:29 pm
SJU
-
LGA
8h 13m
1 stop
$281American Airlines
Tue, Sep 1 - Tue, Sep 8
JetBlue Logo
8:00 pm - 12:13 am
JFK
-
SJU
4h 13mnonstop
JetBlue Logo
5:01 am - 8:54 am
SJU
-
JFK
3h 53mnonstop
$282JetBlue
Tue, Aug 11 - Fri, Aug 14
JetBlue Logo
8:00 pm - 12:13 am
JFK
-
SJU
4h 13mnonstop
JetBlue Logo
5:01 am - 8:54 am
SJU
-
JFK
3h 53mnonstop
$285JetBlue
Thu, Oct 22 - Wed, Oct 28
United Airlines Logo
6:00 am - 12:34 pm
LGA
-
SJU
6h 34m
1 stop
United Airlines Logo
7:25 am - 4:05 pm
SJU
-
LGA
8h 40m
1 stop
$285United Airlines
Sat, Aug 29 - Sun, Sep 6
United Airlines Logo
8:05 am - 8:38 pm
LGA
-
SJU
12h 33m
2 stops
United Airlines Logo
7:00 am - 4:45 pm
SJU
-
LGA
9h 45m
1 stop
$286United Airlines
Tue, Aug 11 - Thu, Aug 13
Delta Logo
7:28 pm - 11:52 pm
JFK
-
SJU
4h 24mnonstop
Delta Logo
7:30 am - 11:25 am
SJU
-
JFK
3h 55mnonstop
$287Delta
Sat, Sep 5 - Sat, Sep 12
Delta Logo
7:28 pm - 11:52 pm
JFK
-
SJU
4h 24mnonstop
Delta Logo
7:30 am - 11:23 am
SJU
-
JFK
3h 53mnonstop
$292Delta
Wed, Sep 30 - Wed, Oct 14
Arajet Logo
12:00 pm - 7:30 pm
EWR
-
AUA
7h 30m
1 stop
Arajet Logo
8:15 pm - 10:30 am
AUA
-
EWR
14h 15m
2 stops
$393Arajet
Sat, Sep 19 - Sun, Sep 27
Arajet Logo
12:59 am - 10:15 am
EWR
-
AUA
9h 16m
1 stop
Arajet Logo
11:00 am - 10:30 am
AUA
-
EWR
23h 30m
2 stops
$394Arajet
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 5 days was to San Juan, at $142 round-trip. The most popular route is from New York John F Kennedy Intl Airport (JFK) to Santiago de los Caballeros (STI), and the cheapest round-trip airline ticket found on this route in the last 5 days was $396.

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

The average price for all round-trip flights from New York to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $296 on average. Morning departures are around 1% 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 $358.

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 $599, 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 September, when tickets cost $405 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $626 and $606 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 Monday, 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 Friday 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 2 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$92
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Newark Liberty Airport to Oranjestad

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.

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.
7.8
DeltaOverall score based on 8465 reviews
8.1Boarding
8.5Crew
7.8Entertainment
7.2Food
7.8Comfort
Airline reviews

FA was a bit strange and dodgy not very characteristic of Delta

6.0 GoodSaad, Jun 2026
LGA - ATL
Read more Delta reviews

FA was a bit strange and dodgy not very characteristic of Delta

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Everything except the food and entertainment. It was a great experience though

Flight was delayed from 35 minute delayed aircraft arrival to 90 minute delay causing us to miss international connecting flight on SWISS resulting in 16 hour delay to reach detonation causing significant angst, monetary loss and discomfort. SWISS transfer desk and staff was like robots not willing to help at all.

Best part: It’s operated by All Nippon Airways. It’s quite literally comfortable, reliable and respected from boarding to landing each and every time. It’s perfection without extremity in lavishness — it’s how flying should always be!

Delays!!! Serious delays. I was told by a member of staff in LGA that I would miss my DEN to LAX flight connection, so I was put on a later flight. Due to delays I would have been able to have made my original flight, where I was sat in business class - seat 1A: I was put on my original flight but bumped from business - 1A to economy 33C. I want a refund for paying business class but only flying economy

The plane was delayed coming in and on the tarmac. I was coming from another flight so it made for a very long day. The stewardess kept trying to slam the overhead bins closed and I was worried that she had damaged my new luggage. They ran out of snacks and lccdsddd me a hummus box which was nice. It took them a very long time to pick up the garbage so I could not go to the washroom and had little time. To prepare for disbarment. The TV system was hard to control from the armrest and picture wasn’t clear. The crew did apologize several times for the lateness. It took the Denver airport an unusually long time to de-ice the plane.

Their app did not recognize my Aeroplan frequent flyer number and would not allow me access to my boarding card. Ground staff was readily available at the airport to print it out to me.

Excellent as always. Service was excellent and fully bilingual. Cannot complain .Will travel again. Always have and will continue. Highly recommended.

I don’t like the music section but I believe it was a cost decision. I changed my flight last minute due to work issues and had to sit way in the back. The seats were way closer together than I would have preferred.

Our particular exceptional experience was with Johnny at JFK at check in. He was the kindest, most accommodating agent I’ve ever encountered taking extra steps to help my husband and I with our extra baggage. I hope that he knows how much he positively affected our trip.

The flight attendant was very polite and attentive. The food was good.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

Maybe focus more on delivering a good product vs selling me a damn credit card

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

Domestic flights are good. Just stay away from international travel

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

Boarding process was terrible. No assigned seat until the gate, then a long line to get seat assignment.

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

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.