$125 Find Cheap Flights from New York to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from New York to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$427
Santo Domingo
Santo Domingononstop$304
Montego Bay
Montego Bay1 stop$356
Oranjestad
Oranjestadnonstop$348
Nassau
Nassau1 stop$316
Kingston
Kingston1 stop$397
Simpson Bay
Simpson Baynonstop$270
Providenciales
Providenciales1 stop$358
Port of Spain
Port of Spain1 stop$425
Bridgetown
Bridgetown1 stop$375
George Town
George Town1 stop$311
Willemstad
Willemstad2 stops$334
Castries
Castries1 stop$512
Aguadilla
Aguadilla1 stop$296
St. John's
St. John'snonstop$446
Puerto Plata
Puerto Plata1 stop$455
Punta Cana
Punta Cana1 stop$427
Santo Domingo
Santo Domingononstop$304
Montego Bay
Montego Bay1 stop$356
Oranjestad
Oranjestadnonstop$348
Nassau
Nassau1 stop$316
Kingston
Kingston1 stop$397
Simpson Bay
Simpson Baynonstop$270
Providenciales
Providenciales1 stop$358
Port of Spain
Port of Spain1 stop$425
Bridgetown
Bridgetown1 stop$375
George Town
George Town1 stop$311
Willemstad
Willemstad2 stops$334
Castries
Castries1 stop$512
Aguadilla
Aguadilla1 stop$296
St. John's
St. John'snonstop$446
Puerto Plata
Puerto Plata1 stop$455
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 to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from New York found in the last 5 days was to San Juan, at $232 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 5 days was $232.

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 afternoon, when round-trip flights cost $299 on average. Morning departures are around 1% more expensive than evening flights, 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 $368.

Can I save money by flying with a layover from New York to Caribbean Islands?

No, with an average price for the route of $615, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from New York to Caribbean Islands?

The cheapest month for flights from New York to Caribbean Islands is January, when tickets cost $435 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $636 and $634 respectively.

What’s the cheapest day of the week to fly from New York to Caribbean Islands?

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from New York to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

How far in advance should I book a flight from New York to Caribbean Islands?

To get a below average price on the flight from New York to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 12% 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

$125
Best time to beat the crowds with an average 11% 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 New York to Caribbean Islands: the best tips from KAYAK users

Insights shared by verified travelers 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
Verified travelerFlew with United Airlines-Apr 2024
Early check in online, get on time for the flight

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 travelers 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 5 airlines serving from New York to Caribbean Islands

 
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.
7.8
DeltaOverall score based on 8536 reviews
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

The actual flight was smooth and we arrived earlier than expected which was great. The flight attendants gave unclear instructions and were rude. They seemed overwhelmed or flustered for the flight. Inflight service was delayed and unsure why.

6.0 GoodCynthia, Aug 2026
Read more Delta reviews

The actual flight was smooth and we arrived earlier than expected which was great. The flight attendants gave unclear instructions and were rude. They seemed overwhelmed or flustered for the flight. Inflight service was delayed and unsure why.

There were weather issues in the area apparently; however, that was not obvious from what we saw outside of LaGuardia. We were delayed leaving (which I understand); however, once we were on the plane we didn't leave for a long time. It may have been two hours?? - all I know is that we sat there for a long time with no information as to why we were not taking off. Finally, after 45 minutes to an hour (maybe?), the pilot gave us an update that no planes were able to go in the our flight path direction (or something like that) due to weather. There was nothing additional added. What does this mean? Why is this? What are the options? When will you give us another update? There were no updates for maybe another 30-45 minutes. There was no explanation as to why we couldn't be rerouted to avoid the weather. We had no information at all. We just sat on the plane (for about 2 hours) with very limited information. All I would have wanted is an explanation as to what was going on. Tell me there is bad weather coming our way. Tell me they are working to reroute us around it (which is what they did). Tell me SOMETHING.

My 4pm flight did not leave until about 10pm. I did not enjoy this experience.

Had one of the worst travel experiences I've ever had. 1.5-hour delay turned into being held on the tarmac and our pilots timing out. Was supposed to take off at 4pm and didn't take off until 10:30pm.

Great people making you feel great and pointing you in the right direction always

We were delayed 2 hours because of a broken seat. Other than that it was a very nice flight.

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

an he late. super rude gate agent, to every person. spoke down at people.

One of the restrooms didn’t work. The ones that did never got replenished. Flight attendant just sitting there on their phone. No notification that the bathroom was broken so long lines. Apathetic crew.

Both of my flights to and from JFK experienced significant delays. Most notably, my first flight was delayed by six hours due to crew members being affected by delays on a previous flight. While I understand that disruptions can occur, Delta’s staffing and operational planning should include sufficient contingency measures to handle situations like this rather than placing the full burden of those delays on customers. Additionally, the $12 meal voucher offered as compensation was inadequate, particularly given the high cost of food and beverages at the airport. Considering the length of the delay and the substantial inconvenience caused, I believe more meaningful compensation would have been appropriate.

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Everything except the food and entertainment. It was a great experience though

Flight was delayed from 35 minute delayed aircraft arrival to 90 minute delay causing us to miss international connecting flight on SWISS resulting in 16 hour delay to reach detonation causing significant angst, monetary loss and discomfort. SWISS transfer desk and staff was like robots not willing to help at all.

Best part: It’s operated by All Nippon Airways. It’s quite literally comfortable, reliable and respected from boarding to landing each and every time. It’s perfection without extremity in lavishness — it’s how flying should always be!

Delays!!! Serious delays. I was told by a member of staff in LGA that I would miss my DEN to LAX flight connection, so I was put on a later flight. Due to delays I would have been able to have made my original flight, where I was sat in business class - seat 1A: I was put on my original flight but bumped from business - 1A to economy 33C. I want a refund for paying business class but only flying economy

The plane was delayed coming in and on the tarmac. I was coming from another flight so it made for a very long day. The stewardess kept trying to slam the overhead bins closed and I was worried that she had damaged my new luggage. They ran out of snacks and lccdsddd me a hummus box which was nice. It took them a very long time to pick up the garbage so I could not go to the washroom and had little time. To prepare for disbarment. The TV system was hard to control from the armrest and picture wasn’t clear. The crew did apologize several times for the lateness. It took the Denver airport an unusually long time to de-ice the plane.

Their app did not recognize my Aeroplan frequent flyer number and would not allow me access to my boarding card. Ground staff was readily available at the airport to print it out to me.

Excellent as always. Service was excellent and fully bilingual. Cannot complain .Will travel again. Always have and will continue. Highly recommended.

Aa cancelled my flight where I was in first class seat 4B. They auto rebooked me on another flight, did not give me a seat assignment until at the gate. Where I got seat 29f, for a 4 hr flight. No accommodation at all for my first class ticket. Left 3 hrs late as well.

It was delayed 5 hours due weather and your app should be rebuilt or disabled. I could not change my original flight on delta so I did it through the delta app. Then rebooked on American once delta cancelled all flights from LGA to PIT on 8/27. American Airlines was fine once the flight took off 5 hours later. I wish my company would find a better provider than kayak.

DCA-LAX No screen on a 5 hour flight (almost) no food for sale on a 5 hour flight (practically) no wifi coverage or speed on a 5 hour flight I should have gotten my money back, shame on American

A crew member's attitude towards a couple passengers who couldn't speak English was rude. Just because they didn't understand what the passenger said, they were not given any snack.

The entire process could’ve been better. Delayed multiple times and American lied and said it was due to Weather in New York, even though other flights were taking off the entire time (including other American Airlines flights)

There were alot of delays without any information. First, my original flight was overbooked so I volunteered to stay back. The layover was hell, I sat in the airport for 4 hours. I was highly disappointed because no one was around to provide answers.

Great. Clean. Seats comfortable. Food was free. Had new release movies.

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

The plane was filthy and worn - the seat pockets were stuffed with tattered food and torn pamphlets. The cleaning crew that came on as we were deboarding were grabbing handfulls of trash and perfunctorily wiping down tables with dishrags. It's been a while since I flew Jetblue and it used to be a great experience. After this flight I will avoid flying Jetblue again if there is any alternative.

JFK is the worst airport and JetBlue is the worst airline

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

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 got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to New York