C$ 176 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 9/6. 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$ 507
Montego Bay
Montego BaydirectC$ 434
Kingston
Kingston1 stopC$ 656
Port of Spain
Port of Spain1 stopC$ 527
Santo Domingo
Santo DomingodirectC$ 540
Punta Cana
Punta CanadirectC$ 507
Montego Bay
Montego BaydirectC$ 434
Kingston
Kingston1 stopC$ 656
Port of Spain
Port of Spain1 stopC$ 527
Santo Domingo
Santo DomingodirectC$ 540

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, 4 Jul - Tue, 14 Jul
Delta Logo
7:25 p.m. - 11:43 p.m.
JFK
-
SJU
4h 18mdirect
Delta Logo
7:35 a.m. - 11:30 a.m.
SJU
-
JFK
3h 55mdirect
C$ 378Delta
Tue, 9 Jun - Sat, 13 Jun
JetBlue Logo
9:30 p.m. - 1:38 a.m.
JFK
-
SJU
4h 08mdirect
JetBlue Logo
3:34 p.m. - 7:43 p.m.
SJU
-
JFK
4h 09mdirect
C$ 390JetBlue
Tue, 2 Jun - Thu, 4 Jun
Delta Logo
7:20 p.m. - 11:35 p.m.
JFK
-
SJU
4h 15mdirect
Delta Logo
6:00 p.m. - 10:15 p.m.
SJU
-
JFK
4h 15mdirect
C$ 398Delta
Thu, 28 May - Wed, 3 Jun
JetBlue Logo
9:30 p.m. - 1:38 a.m.
JFK
-
SJU
4h 08mdirect
JetBlue Logo
6:30 a.m. - 10:32 a.m.
SJU
-
JFK
4h 02mdirect
C$ 400JetBlue
Mon, 10 Aug - Wed, 19 Aug
American Airlines Logo
8:30 p.m. - 9:43 a.m.
JFK
-
SJU
13h 13m
1 stop
American Airlines Logo
10:33 a.m. - 9:30 p.m.
SJU
-
JFK
10h 57m
1 stop
C$ 423American Airlines
Fri, 15 May - Tue, 19 May
American Airlines Logo
7:58 a.m. - 8:51 p.m.
JFK
-
SJU
12h 53m
1 stop
American Airlines Logo
5:45 a.m. - 1:06 p.m.
SJU
-
JFK
7h 21m
1 stop
C$ 432American Airlines
Sun, 31 May - Thu, 4 Jun
Copa Airlines Logo
6:00 a.m. - 2:36 p.m.
JFK
-
CUR
8h 36m
1 stop
Copa Airlines Logo
3:39 p.m. - 3:59 a.m.
CUR
-
JFK
12h 20m
1 stop
C$ 638Copa Airlines
Thu, 17 Sep - Sun, 20 Sep
Copa Airlines Logo
3:32 p.m. - 11:32 a.m.
JFK
-
POP
20h 00m
1 stop
Copa Airlines Logo
12:41 p.m. - 1:00 a.m.
POP
-
JFK
12h 19m
1 stop
C$ 679Copa Airlines
Tue, 12 May - Fri, 15 May
Caribbean Airlines Logo
5:00 a.m. - 5:20 p.m.
JFK
-
CUR
12h 20m
2 stops
Caribbean Airlines Logo
6:20 p.m. - 11:50 p.m.
CUR
-
JFK
29h 30m
2 stops
C$ 713Caribbean Airlines
Wed, 3 Jun - Wed, 17 Jun
Caribbean Airlines Logo
5:00 a.m. - 5:40 p.m.
JFK
-
ANU
12h 40m
2 stops
Caribbean Airlines Logo
6:25 p.m. - 11:50 p.m.
ANU
-
JFK
29h 25m
1 stop
C$ 764Caribbean 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 Oranjestad, at C$ 434 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$ 657.

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

The average price for all round-trip flights from New York John F Kennedy Intl Airport 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 morning, when round-trip flights cost C$ 629 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$ 629.

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$ 853, 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$ 517 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is C$ 877 and C$ 750 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 3 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flightC$ 176
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly (18% 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.

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 226 reviews
6.6Entertainment
6.8Food
7.8Comfort
8.3Crew
8.0Boarding
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.

Delayed for 3 hours- little to no communication about this and staff moves in slow motion

Caribbean airline sucks… they have a promotion to bring 60lbs in your suitcase.. meanwhile when you reached your destination (JFK)… your suitcase didn’t show up. They had too much weight so the suitcase was left in Guyana… like WTF????? Stupid promotion.. just like the uneducated people working with the airline. The representative said there is nothing she can do about it… will not use them again.

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.

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.

I am still at the Airport! Delayed Delayed and Delyaed

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

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

It was good. The leg room was not great in Row 1.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports