C$ 188 Find Cheap Flights from New York to Caribbean Islands – 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 New York to Caribbean Islands departing on 2/10. 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.
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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$ 635
Montego Bay
Montego Bay1 stopC$ 562
Kingston
Kingston1 stopC$ 708
Port of Spain
Port of Spain1 stopC$ 615
Santo Domingo
Santo DomingodirectC$ 597
Punta Cana
Punta CanadirectC$ 635
Montego Bay
Montego Bay1 stopC$ 562
Kingston
Kingston1 stopC$ 708
Port of Spain
Port of Spain1 stopC$ 615
Santo Domingo
Santo DomingodirectC$ 597

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

Fri, 25 Sep - Sat, 19 Dec
Delta Logo
7:29 p.m. - 11:49 p.m.JFK  New York John F Kennedy Intl-SJU San Juan Luis Munoz Marin Intl
4h 20mdirect
Delta Logo
6:05 p.m. - 9:27 p.m.SJU  San Juan Luis Munoz Marin Intl-JFK New York John F Kennedy Intl
4h 22mdirect
C$ 382Delta
Tue, 25 Aug - Tue, 1 Sep
Delta Logo
12:40 p.m. - 4:33 p.m.JFK  New York John F Kennedy Intl-SJU San Juan Luis Munoz Marin Intl
3h 53mdirect
Delta Logo
7:30 a.m. - 11:25 a.m.SJU  San Juan Luis Munoz Marin Intl-JFK New York John F Kennedy Intl
3h 55mdirect
C$ 382Delta
Tue, 25 Aug - Thu, 3 Sep
JetBlue Logo
5:30 p.m. - 9:40 p.m.JFK  New York John F Kennedy Intl-SJU San Juan Luis Munoz Marin Intl
4h 10mdirect
JetBlue Logo
5:01 a.m. - 8:54 a.m.SJU  San Juan Luis Munoz Marin Intl-JFK New York John F Kennedy Intl
3h 53mdirect
C$ 389JetBlue
Tue, 25 Aug - Tue, 1 Sep
JetBlue Logo
5:30 p.m. - 9:40 p.m.JFK  New York John F Kennedy Intl-SJU San Juan Luis Munoz Marin Intl
4h 10mdirect
JetBlue Logo
5:01 a.m. - 8:54 a.m.SJU  San Juan Luis Munoz Marin Intl-JFK New York John F Kennedy Intl
3h 53mdirect
C$ 389JetBlue
Sun, 25 Oct - Mon, 2 Nov
Delta Logo
8:00 a.m. - 12:05 p.m.JFK  New York John F Kennedy Intl-SJU San Juan Luis Munoz Marin Intl
4h 05mdirect
Delta Logo
7:45 a.m. - 10:44 a.m.SJU  San Juan Luis Munoz Marin Intl-JFK New York John F Kennedy Intl
3h 59mdirect
C$ 389Delta
Wed, 21 Oct - Mon, 9 Nov
Delta Logo
8:00 a.m. - 12:05 p.m.JFK  New York John F Kennedy Intl-SJU San Juan Luis Munoz Marin Intl
4h 05mdirect
Delta Logo
6:30 p.m. - 9:47 p.m.SJU  San Juan Luis Munoz Marin Intl-JFK New York John F Kennedy Intl
4h 17mdirect
C$ 389Delta
Mon, 7 Sep - Wed, 16 Sep
JetBlue Logo
5:50 a.m. - 1:32 p.m.JFK  New York John F Kennedy Intl-AUA Oranjestad Reina Beatrix
7h 42m1 stop Fort Lauderdale
JetBlue Logo
1:40 p.m. - 6:19 p.m.AUA  Oranjestad Reina Beatrix-JFK New York John F Kennedy Intl
4h 39mdirect
C$ 518JetBlue
Thu, 26 Nov - Thu, 17 Dec
American Airlines Logo
9:30 p.m. - 10:05 a.m.JFK  New York John F Kennedy Intl-SDQ Santo Domingo Las Americas
11h 35m1 stop Miami
American Airlines Logo
4:49 p.m. - 11:23 p.m.SDQ  Santo Domingo Las Americas-JFK New York John F Kennedy Intl
7h 34m1 stop Miami
C$ 640American Airlines
Wed, 26 Aug - Sat, 5 Sep
American Airlines Logo
9:00 p.m. - 9:25 a.m.JFK  New York John F Kennedy Intl-SDQ Santo Domingo Las Americas
12h 25m1 stop Miami
American Airlines Logo
2:22 p.m. - 11:00 p.m.SDQ  Santo Domingo Las Americas-JFK New York John F Kennedy Intl
8h 38m1 stop Miami
C$ 684American Airlines
Tue, 8 Sep - Sat, 12 Sep
American Airlines Logo
5:55 a.m. - 1:22 p.m.JFK  New York John F Kennedy Intl-SDQ Santo Domingo Las Americas
7h 27m1 stop Miami
American Airlines Logo
4:20 p.m. - 12:59 a.m.SDQ  Santo Domingo Las Americas-JFK New York John F Kennedy Intl
8h 39m1 stop Miami
C$ 692American 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 5 days was to Nassau, at C$ 182 round-trip. The most popular route is from New York John F Kennedy Intl Airport (JFK) to Oranjestad (AUA), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 540.

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$ 647 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$ 647.

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$ 1,002, 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 October, when tickets cost C$ 579 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is C$ 906 and C$ 882 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 2% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

September
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly (12% more expensive on average)

Flights from New York to Caribbean Islands: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from New York to Caribbean Islands 
NicoleFlew with Delta-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-Aug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix

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 229 reviews
7.8Comfort
8.3Crew
6.8Food
8.0Boarding
6.7Entertainment
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
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.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports