$95 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 4/21. 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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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$306
Santo Domingo
Santo Domingo1 stop$265
Montego Bay
Montego Bay2 stops$287
Oranjestad
Oranjestad2 stops$297
Nassau
Nassau1 stop$356
Kingston
Kingston1 stop$335
Simpson Bay
Simpson Bay1 stop$339
Providenciales
Providenciales1 stop$378
Port of Spain
Port of Spainnonstop$335
Bridgetown
Bridgetown1 stop$372
George Town
George Townnonstop$322
Willemstad
Willemstad2 stops$274
Castries
Castries2 stops$450
Puerto Plata
Puerto Platanonstop$460
St. John's
St. John'snonstop$367
Aguadilla
Aguadilla1 stop$223
Punta Cana
Punta Cana1 stop$306
Santo Domingo
Santo Domingo1 stop$265
Montego Bay
Montego Bay2 stops$287
Oranjestad
Oranjestad2 stops$297
Nassau
Nassau1 stop$356
Kingston
Kingston1 stop$335
Simpson Bay
Simpson Bay1 stop$339
Providenciales
Providenciales1 stop$378
Port of Spain
Port of Spainnonstop$335
Bridgetown
Bridgetown1 stop$372
George Town
George Townnonstop$322
Willemstad
Willemstad2 stops$274
Castries
Castries2 stops$450
Puerto Plata
Puerto Platanonstop$460
St. John's
St. John'snonstop$367
Aguadilla
Aguadilla1 stop$223

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

Sat, May 9 - Tue, May 12
Multiple Airlines Logo
11:30 am - 2:08 am
EWR
-
SJU
14h 38m
1 stop
Multiple Airlines Logo
12:59 am - 5:06 am
SJU
-
EWR
4h 07mnonstop
$213Multiple Airlines
Mon, May 18 - Mon, Jun 1
Frontier Logo
5:55 am - 2:07 pm
EWR
-
SJU
8h 12m
1 stop
Frontier Logo
6:09 pm - 10:32 am
SJU
-
EWR
16h 23m
1 stop
$214Frontier
Wed, May 6 - Sun, May 10
Spirit Airlines Logo
6:42 pm - 10:42 pm
EWR
-
SJU
4h 00mnonstop
Spirit Airlines Logo
8:04 pm - 9:04 am
SJU
-
EWR
13h 00m
1 stop
$216Spirit Airlines
Sat, May 2 - Sun, May 10
Spirit Airlines Logo
5:45 am - 9:45 am
EWR
-
SJU
4h 00mnonstop
Spirit Airlines Logo
12:59 am - 5:06 am
SJU
-
EWR
4h 07mnonstop
$218Spirit Airlines
Sat, Apr 18 - Tue, Apr 28
JetBlue Logo
9:59 pm - 2:07 am
JFK
-
SJU
4h 08mnonstop
JetBlue Logo
7:15 pm - 11:19 pm
SJU
-
JFK
4h 04mnonstop
$283JetBlue
Tue, Apr 21 - Sat, Apr 25
JetBlue Logo
8:00 pm - 12:07 am
JFK
-
SJU
4h 07mnonstop
JetBlue Logo
6:25 am - 10:29 am
SJU
-
JFK
4h 04mnonstop
$284JetBlue
Sat, Apr 18 - Thu, Apr 23
Delta Logo
7:38 pm - 11:59 pm
JFK
-
SJU
4h 21mnonstop
Delta Logo
5:42 pm - 9:59 pm
SJU
-
JFK
4h 17mnonstop
$296Delta
Fri, Apr 24 - Tue, Apr 28
Delta Logo
7:38 pm - 11:59 pm
JFK
-
SJU
4h 21mnonstop
Delta Logo
7:15 am - 11:18 am
SJU
-
JFK
4h 03mnonstop
$297Delta
Sun, Apr 26 - Sat, May 2
Arajet Logo
12:00 pm - 4:19 pm
EWR
-
PUJ
4h 19mnonstop
Arajet Logo
7:10 pm - 11:30 pm
PUJ
-
EWR
4h 20mnonstop
$307Arajet
Sun, May 10 - Thu, May 21
Arajet Logo
12:00 pm - 4:19 pm
EWR
-
PUJ
4h 19mnonstop
Arajet Logo
7:10 pm - 11:30 pm
PUJ
-
EWR
4h 20mnonstop
$310Arajet
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 $109 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 $266.

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 $280 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $338.

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 $549, 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 October, when tickets cost $216 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $358 and $354 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 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$95
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 18% 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.

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
DeltaOverall score based on 8388 reviews
7.8Entertainment
7.9Comfort
7.2Food
8.1Boarding
8.5Crew
Airline reviews

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

2.0 MediocreWilliam, Apr 2026
LGA - BOS
Read more Delta reviews

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

I am still at the Airport! Delayed Delayed and Delyaed

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Delayed. Hot. Passenger next to me was so large I couldn’t move.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

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

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

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.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

Flight on time. Excellent service in Premium Economy. Great food served and cleaned up promptly. Unfortunately the climate control was malfunctioning and it was very cold and felt a bit like camping. Cold helps with sleep though so not complaining too much. Slept well. It asks to rate "entertainment". I do not like any IFE, don't shove a big screen in my face—I have my own phone if I want it. So this will always get low ratings.

Once boarding started it was pretty quick. Food was inedible; cold and salty..

Much better than Spirit. I was please by the easy fast check in and boarding

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

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!

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

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.

For an international flight the seats were smaller than most flight I have been on in economy. I don’t know the size of the seats or perhaps it was the size of the seat dividers that made the seats feel smaller and little amount of space to even turn your body if you needed to

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

There were no TV screens - even in Business class. 5 delays, and only given $12 meal voucher! Terrible!

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

The food for sale on board has opportunity for improvement.

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.