$138 Find Cheap Flights from New York John F Kennedy Airport to Caribbean - 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 John F Kennedy Intl to Caribbean departing on 9/29. 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 John F Kennedy Intl to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$455
Santo Domingo
Santo Domingononstop$423
Montego Bay
Montego Bay2 stops$404
Oranjestad
Oranjestadnonstop$375
Nassau
Nassaunonstop$361
Kingston
Kingston2 stops$499
Simpson Bay
Simpson Baynonstop$362
Providenciales
Providencialesnonstop$393
Port of Spain
Port of Spain1 stop$431
Bridgetown
Bridgetown1 stop$475
George Town
George Town1 stop$424
Willemstad
Willemstad1 stop$532
Castries
Castries1 stop$472
Aguadilla
Aguadillanonstop$344
St. John's
St. John's1 stop$457
Puerto Plata
Puerto Plata1 stop$552
Punta Cana
Punta Cananonstop$455
Santo Domingo
Santo Domingononstop$423
Montego Bay
Montego Bay2 stops$404
Oranjestad
Oranjestadnonstop$375
Nassau
Nassaunonstop$361
Kingston
Kingston2 stops$499
Simpson Bay
Simpson Baynonstop$362
Providenciales
Providencialesnonstop$393
Port of Spain
Port of Spain1 stop$431
Bridgetown
Bridgetown1 stop$475
George Town
George Town1 stop$424
Willemstad
Willemstad1 stop$532
Castries
Castries1 stop$472
Aguadilla
Aguadillanonstop$344
St. John's
St. John's1 stop$457
Puerto Plata
Puerto Plata1 stop$552

Book Cheap John F Kennedy Intl to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from John F Kennedy Intl to Caribbean 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 John F Kennedy Intl to Caribbean

Wed, Aug 19 - Wed, Sep 2
JetBlue Logo
5:30 pm - 9:40 pm
JFK
-
SJU
4h 10mnonstop
JetBlue Logo
5:01 am - 8:54 am
SJU
-
JFK
3h 53mnonstop
$272JetBlue
Mon, Sep 21 - Mon, Sep 28
JetBlue Logo
3:30 pm - 10:27 pm
JFK
-
SJU
6h 57m
1 stop
JetBlue Logo
6:00 am - 9:52 am
SJU
-
JFK
3h 52mnonstop
$272JetBlue
Thu, Aug 27 - Tue, Sep 29
American Airlines Logo
3:30 pm - 11:59 pm
JFK
-
SJU
8h 29m
1 stop
American Airlines Logo
6:00 am - 8:00 pm
SJU
-
JFK
14h 00m
2 stops
$276American Airlines
Tue, Aug 25 - Thu, Sep 10
American Airlines Logo
2:30 pm - 9:55 pm
JFK
-
SJU
7h 25m
1 stop
American Airlines Logo
3:41 pm - 10:43 pm
SJU
-
JFK
7h 02m
1 stop
$276American Airlines
Wed, Aug 26 - Tue, Sep 1
Delta Logo
12:40 pm - 4:33 pm
JFK
-
SJU
3h 53mnonstop
Delta Logo
1:19 pm - 5:30 pm
SJU
-
JFK
4h 11mnonstop
$277Delta
Wed, Aug 26 - Thu, Sep 3
Delta Logo
7:28 pm - 11:52 pm
JFK
-
SJU
4h 24mnonstop
Delta Logo
5:50 pm - 10:04 pm
SJU
-
JFK
4h 14mnonstop
$277Delta
Mon, Sep 7 - Tue, Sep 15
KLM Logo
7:42 am - 12:40 pm
JFK
-
AUA
4h 58mnonstop
KLM Logo
1:55 pm - 7:00 pm
AUA
-
JFK
5h 05mnonstop
$383KLM
Mon, Sep 7 - Wed, Sep 16
KLM Logo
7:42 am - 12:40 pm
JFK
-
AUA
4h 58mnonstop
KLM Logo
1:55 pm - 7:00 pm
AUA
-
JFK
5h 05mnonstop
$384KLM
Tue, Jan 19 - Wed, Jan 27
Copa Airlines Logo
2:20 am - 2:39 pm
JFK
-
AUA
11h 19m
1 stop
Copa Airlines Logo
3:40 pm - 3:00 pm
AUA
-
JFK
24h 20m
1 stop
$417Copa Airlines
Mon, Jan 18 - Thu, Jan 28
Copa Airlines Logo
2:20 am - 6:29 pm
JFK
-
AUA
15h 09m
1 stop
Copa Airlines Logo
7:10 am - 3:00 pm
AUA
-
JFK
8h 50m
1 stop
$417Copa Airlines
Booking Insights

KAYAK's insights & trends for John F Kennedy Intl to Caribbean flights

Get data-powered insights and trends into flights from John F Kennedy Intl to Caribbean 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 flight route?

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

The cheapest ticket to Caribbean from New York John F Kennedy Intl Airport found in the last 5 days was to Nassau, at $170 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 $455.

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

The average price for all round-trip flights from New York John F Kennedy Intl Airport to Caribbean 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 is generally in the afternoon, when round-trip flights cost $297 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $360.

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

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 $590, 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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New York John F Kennedy Intl Airport to Caribbean, 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 John F Kennedy Intl Airport to Caribbean is October, when tickets cost $385 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $627 and $609 respectively.

What’s the cheapest day of the week to fly from New York John F Kennedy Airport to Caribbean?

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

When flying from New York John F Kennedy Airport to Caribbean, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to New York John F Kennedy Airport, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

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

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 John F Kennedy Intl Airport to Caribbean, 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 John F Kennedy Intl Airport to Caribbean, you should book around 4 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

September

Cheapest flight

$138
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from New York John F Kennedy Airport to San Juan Airport

Flights from John F Kennedy Intl to Caribbean: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from John F Kennedy Intl to Caribbean 
NicoleFlew with Delta
JFK
-
SJU
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
JFK
-
SJU
Aug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from New York John F Kennedy Airport to Caribbean?

    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 John F Kennedy Airport to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from New York John F Kennedy Airport to Caribbean 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 John F Kennedy Airport to Caribbean?

    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 John F Kennedy Airport to Caribbean 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 John F Kennedy Airport to Caribbean?

    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 John F Kennedy Airport to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from New York John F Kennedy Airport to the following destinations at these prices or less: San Juan $197 one-way - $326 round-trip; Santiago de los Caballeros $275 one-way - $591 round-trip

Reviews of the top 5 airlines serving from John F Kennedy Intl to Caribbean

 
Need help choosing which airline to fly with from John F Kennedy Intl to Caribbean? 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 229 reviews
7.8Comfort
8.0Boarding
6.7Entertainment
6.8Food
8.3Crew
Airline reviews

Delayed for three hours. This seems to be CAL’s MO when flights aren’t filled until they fill it. Business class is nice but not luxe like other airlines. Lots of space and amazing staff.

6.0 GoodAnonymous, Mar 2026
JFK - POS
Read more Caribbean Airlines reviews

Delayed for three hours. This seems to be CAL’s MO when flights aren’t filled until they fill it. Business class is nice but not luxe like other airlines. Lots of space and amazing staff.

Boarding the flight was smooth and the flight was not full so i had an extra seat essentially

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

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 crew and Culture. However, my seat was too narrow and not too comfortable

When I booked my flight I choose a seat which was the window in the middle of the aircraft. My seating was change without notice and I was in the middle seat which cause me anxiety. Hated this whole flight experience

From the point of checking in I felt as if the agents and crew were like family and friends. The best customer service experience I ever had.

To be honest I did not like anything there because the flight was delay and poor customer service!

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

Our flight was delayed multiple times and then canceled at almost 1 in the morning. We are a family of 7, traveling with 5 young children. When the flight we were supposed to fly on finally arrived after waiting all day after an international flight into JFK we were informed our flight was in need of a copilot and once they located one we would take off. Then our flight was cancelled because the copilot was over his hours and they couldn't locate another. They knew before taking off from the previous location that the copilot would be unable to fly. They could have communicated the cancellation of the flight hours in advance. Once they cancelled and the pilot and copilot got off the flight, they joked about it. While there are understandably limits on flight time for pilots, they can still handle the situation in a professional manner. The late cancellation resulted in angry passengers that required police intervention in the airport. It also occurred so late and included other delta flights that after trying 15 different hotels, we were unable to secure a hotel room, they were all booked. No rental cars were available in the area either. We ended up staying in the airport with the 5 children. We made it home after 54 hours of travel with maybe 2 hours of sleep. Our luggage was lost and had to be claimed at the airport at our final destination. This was the worst trip I have ever taken and the worst airport I have ever spent time in. I met two individuals in the airport that were kind and helpful; Tonya Maingot Williams from the can we hel desk that worked to help get us rebooked and home, as well as provide us with care bags for our extended stay in the airport. The other individual was Danielle from Buffalo Wild Wings that was so very kind when we found a place to take our family we were traveling with to eat, all 11 of us and we were able to sit down together to enjoy a meal during such a stressful time.

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.

Was revoked with Jet Blue due to delay from Kenya Air

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.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

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.

The boarding crew was very helpful with a little special problem I had. The inflight crew - so-so.

They kept us on the tarmac for 6 hours after already delaying our flight by 2 hours. No one had any answers. They sent our gate checked stroller to baggage claim instead of giving it back at the gate.

There was a big delay and I missed my connection flight

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.

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

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

It was a smooth flight and the pilot was very pleasant

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

Domestic flights are good. Just stay away from international travel

Flight was delayed but it was very smooth. Crew was very nice. Seats are uncomfortable but ok.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

The flight left over two hours late. They charged me $180 to bring a carry on. There was an error with the spelling of my name and Frontair agent lied that I would need to pay $200 for her to fix the spelling, and pressured me that if I don't do it quick I would lose the flight. I called back and another agent said it costs $75 to fix. All in all, this company is a complete scam.

I took my first and last flight with FRONTIER. The seats are not able to be reclined so it’s not a very comfortable experience when you take a flight of 3 hours or longer. You must pay for your luggage either carry on or check in, so taking all this in consideration at the end what you think you’re saving your paying in services that should be included. Not a beverage in sight. . You’re seriously better off getting on a proper airline such as Delta, AA, United, etc.

They never updated the boarding pass on their apps to show their delay

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Frontier system that tracts what you’ve paid for is horrible. I brought bags, tried to upgrade the weight of bag. Did it via the text service on their site. Got to the airport and they had no idea what was going on. Ended up paying way more than I was supposed to

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports