C$ 135 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 12/10. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Caribbean Islands, as well as popular online travel agencies
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Flight 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 CanadirectC$ 388
Montego Bay
Montego BaydirectC$ 495
Kingston
Kingston1 stopC$ 528
Port of Spain
Port of SpaindirectC$ 487
Santo Domingo
Santo Domingo1 stopC$ 433
Punta Cana
Punta CanadirectC$ 388
Montego Bay
Montego BaydirectC$ 495
Kingston
Kingston1 stopC$ 528
Port of Spain
Port of SpaindirectC$ 487
Santo Domingo
Santo Domingo1 stopC$ 433

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

Sat, 11 Oct - Sat, 11 Oct
JetBlue Logo
8:40 p.m. - 12:47 a.m.JFK-SJU
4h 07mdirect
JetBlue Logo
3:03 a.m. - 7:00 a.m.SJU-JFK
3h 57mdirect
C$ 263JetBlue
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Mon, 13 Oct - Fri, 17 Oct
JetBlue Logo
5:25 p.m. - 9:24 p.m.JFK-SJU
3h 59mdirect
JetBlue Logo
2:25 p.m. - 6:20 p.m.SJU-JFK
3h 55mdirect
C$ 270JetBlue
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Sun, 5 Oct - Sun, 12 Oct
Delta Logo
12:25 p.m. - 4:20 p.m.JFK-SJU
3h 55mdirect
Delta Logo
7:00 a.m. - 11:02 a.m.SJU-JFK
4h 02mdirect
C$ 277Delta
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Fri, 3 Oct - Fri, 10 Oct
Delta Logo
7:29 p.m. - 11:44 p.m.JFK-SJU
4h 15mdirect
Delta Logo
6:00 p.m. - 10:11 p.m.SJU-JFK
4h 11mdirect
C$ 283Delta
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Thu, 2 Oct - Sat, 11 Oct
JetBlue Logo
8:50 p.m. - 12:57 a.m.JFK-SJU
4h 07mdirect
JetBlue Logo
3:03 a.m. - 7:00 a.m.SJU-JFK
3h 57mdirect
C$ 289JetBlue
Find Deal
Fri, 10 Oct - Mon, 13 Oct
Frontier Logo
11:30 a.m. - 3:24 p.m.JFK-SJU
3h 54mdirect
Frontier Logo
6:22 a.m. - 10:25 a.m.SJU-JFK
4h 03mdirect
C$ 337Frontier
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Fri, 10 Oct - Mon, 13 Oct
Frontier Logo
6:59 a.m. - 2:30 a.m.JFK-SJU
19h 31m1 stop
Frontier Logo
9:19 p.m. - 10:24 a.m.SJU-JFK
13h 05m1 stop
C$ 376Frontier
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Mon, 29 Sep - Mon, 6 Oct
Multiple Airlines Logo
6:00 a.m. - 4:29 p.m.JFK-SDQ
10h 29m1 stop
Multiple Airlines Logo
6:29 p.m. - 1:25 a.m.SDQ-JFK
6h 56m1 stop
C$ 433Multiple Airlines
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Wed, 5 Nov - Wed, 12 Nov
Caribbean Airlines Logo
12:10 a.m. - 11:00 a.m.JFK-ANU
9h 50m2 stops
Caribbean Airlines Logo
6:25 p.m. - 10:15 p.m.ANU-JFK
28h 50m1 stop
C$ 581Caribbean Airlines
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Wed, 8 Oct - Sun, 12 Oct
Caribbean Airlines Logo
1:10 a.m. - 11:00 a.m.JFK-ANU
9h 50m2 stops
Caribbean Airlines Logo
6:05 p.m. - 11:55 p.m.ANU-JFK
29h 50m2 stops
C$ 608Caribbean Airlines
Find Deal
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 John F Kennedy Intl Airport 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 John F Kennedy Intl Airport found in the last 72 hours was to San Juan, at C$ 159 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 C$ 159.

Can I save money by flying with a layover from New York John F Kennedy Intl Airport 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 C$ 906, 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 Islands?

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 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 John F Kennedy Intl Airport to Caribbean Islands is September, when tickets cost C$ 495 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is C$ 805 and C$ 733 respectively.

How far in advance should I book a flight from New York John F Kennedy Intl Airport 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 John F Kennedy Intl Airport 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 a flight from New York John F Kennedy Intl Airport to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 4% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flightC$ 135
Best time to beat the crowds (9% less expensive on average)
Most popular time to fly (26% more expensive on average)
Flight from New York John F Kennedy Airport to San Juan

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 travellers 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 morning, when round-trip flights cost C$ 482 on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is C$ 482.

Reviews of the top 3 airlines flying 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.
8.1
Caribbean AirlinesOverall score based on 178 reviews
7.9Comfort
8.1Boarding
6.8Food
8.4Crew
6.8Entertainment
Airline reviews

just a child who screamed and threw tantrums the entire flight

8.0 ExcellentAnonymous, Sep 2025YYZ - POS
Read more Caribbean Airlines reviews

just a child who screamed and threw tantrums the entire flight

Excellent experience this was my first time booking with Kayak.

Flight ended up being longer than anticipated because we had to reroute to the Bahamas. So a hour and half flight turned into 5 hours. 0/10.

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

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

I believe that a four-hour trip should have a meal. Delta had none.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

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.

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

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.

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.

Everything you need to know for your flight to Caribbean Islands

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