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 24/2. 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, 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$ 387
Montego Bay
Montego BaydirectC$ 444
Kingston
Kingston1 stopC$ 577
Port of Spain
Port of SpaindirectC$ 504
Santo Domingo
Santo DomingodirectC$ 440
Punta Cana
Punta CanadirectC$ 387
Montego Bay
Montego BaydirectC$ 444
Kingston
Kingston1 stopC$ 577
Port of Spain
Port of SpaindirectC$ 504
Santo Domingo
Santo DomingodirectC$ 440

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

Thu, 16 Apr - Tue, 21 Apr
Frontier Logo
6:29 a.m. - 10:26 a.m.
JFK
-
SJU
3h 57mdirect
Frontier Logo
3:08 a.m. - 11:50 a.m.
SJU
-
JFK
8h 42m
1 stop
C$ 231Frontier
Thu, 26 Feb - Thu, 5 Mar
Frontier Logo
11:03 a.m. - 12:43 a.m.
JFK
-
SJU
12h 40m
1 stop
Frontier Logo
8:50 a.m. - 12:04 p.m.
SJU
-
JFK
4h 14mdirect
C$ 241Frontier
Thu, 26 Feb - Thu, 5 Mar
Multiple Airlines Logo
7:30 p.m. - 12:29 a.m.
JFK
-
SJU
3h 59mdirect
Multiple Airlines Logo
8:50 a.m. - 12:04 p.m.
SJU
-
JFK
4h 14mdirect
C$ 257Multiple Airlines
Thu, 16 Apr - Tue, 21 Apr
Frontier Logo
1:00 p.m. - 2:01 a.m.
JFK
-
SJU
13h 01m
1 stop
Frontier Logo
3:08 a.m. - 11:50 a.m.
SJU
-
JFK
8h 42m
1 stop
C$ 261Frontier
Sat, 21 Feb - Tue, 24 Feb
JetBlue Logo
11:20 p.m. - 4:11 a.m.
JFK
-
SJU
3h 51mdirect
JetBlue Logo
11:59 p.m. - 2:59 a.m.
SJU
-
JFK
4h 00mdirect
C$ 268JetBlue
Tue, 3 Mar - Fri, 6 Mar
Delta Logo
8:05 a.m. - 1:05 p.m.
JFK
-
SJU
4h 00mdirect
Delta Logo
7:00 a.m. - 10:05 a.m.
SJU
-
JFK
4h 05mdirect
C$ 295Delta
Sat, 28 Feb - Tue, 3 Mar
Delta Logo
6:55 p.m. - 11:56 p.m.
JFK
-
SJU
4h 01mdirect
Delta Logo
6:02 p.m. - 9:27 p.m.
SJU
-
JFK
4h 25mdirect
C$ 309Delta
Mon, 25 May - Sat, 30 May
JetBlue Logo
9:45 p.m. - 1:59 a.m.
JFK
-
SJU
4h 14mdirect
JetBlue Logo
8:10 a.m. - 12:04 p.m.
SJU
-
JFK
3h 54mdirect
C$ 321JetBlue
Tue, 10 Mar - Tue, 17 Mar
Caribbean Airlines Logo
5:00 a.m. - 5:20 p.m.
JFK
-
CUR
12h 20m
2 stops
Caribbean Airlines Logo
6:20 p.m. - 2:25 p.m.
CUR
-
JFK
20h 05m
2 stops
C$ 575Caribbean Airlines
Sat, 14 Mar - Tue, 24 Mar
Caribbean Airlines Logo
5:00 a.m. - 4:00 p.m.
JFK
-
FDF
35h 00m
3 stops
Caribbean Airlines Logo
5:30 p.m. - 2:25 p.m.
FDF
-
JFK
20h 55m
3 stops
C$ 899Caribbean Airlines
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$ 164 round-trip. The most popular route is from New York John F Kennedy Intl Airport (JFK) to Santo Domingo (SDQ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 299.

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$ 830, 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$ 487 (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$ 779 and C$ 732 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 6% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 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 (22% 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$ 640 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 640.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from New York to the following destinations at these prices or less: Santo Domingo C$ 211 one-way - C$ 403 round-trip

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.
7.9
Caribbean AirlinesOverall score based on 213 reviews
7.8Comfort
6.6Entertainment
6.7Food
7.9Boarding
8.3Crew
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
MIA - POS
Read more Caribbean Airlines reviews

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

Overall, it was good. There was no food or entertainment, which is why I put poor (it wasn't an issue though).

Nothing, they could have made some accommodation for an awful experience. Me and my family were not informed properly we we separated. They took me off the original flight i booked. I booked our flight at one price and called me and told me they were not honoring my rate and they charged me double of what I paid. Me and my family don’t want to ever use your services again.

This flight was great. The plane took off and arrived at the destination an hour early. The crew was pleasant. The food and entertainment options are minimal but adequate for a 1-hour flight. They passed out water and quickly supplied me with a fresh magazine since the previous one had the crossword section filled out.

Better movie and tv selections. Also, the overnight flight to Trinidad from Toronto, the staff were not very attentive. I did not see them for at least half the fight. They were behind their curtain a lot of the time, and they did not check on us before landing to make sure all landing requirements were met.

Little space for luggage and the flight was delayed by an hour.

The flight was delayed over a hour and that was over 15 hours in advance not good

At check in I had to pay for my seat that I already paid for on purchasing my ticket. The flight was over an hour late and the plane smelt gross.

just a child who screamed and threw tantrums the entire flight

The flight was comfortable and uneventful, which is what I desire

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

I truly love flying with Delta. They have always treated me with the upmost respect

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight was great. The gate location was way to far away!!!

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.

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.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports