$119 Find Cheap Flights from White Plains to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight $[0,preposition:'from ']$[0,article:'from ']$[0,place:'from'] $[1,preposition:'to ']$[1,article:'to ']$[1,place:'to'] departing on 8/20. 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 Flight Deals from White Plains

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$324
Santo Domingo
Santo Domingo2 stops$419
Montego Bay
Montego Bay2 stops$395
Oranjestad
Oranjestad2 stops$370
Nassau
Nassau1 stop$383
Kingston
Kingston2 stops$473
Simpson Bay
Simpson Bay2 stops$340
Providenciales
Providenciales1 stop$668
George Town
George Town2 stops$384
Willemstad
Willemstad2 stops$525
St. John's
St. John's2 stops$353
Aguadilla
Aguadilla1 stop$440
Punta Cana
Punta Cana2 stops$324
Santo Domingo
Santo Domingo2 stops$419
Montego Bay
Montego Bay2 stops$395
Oranjestad
Oranjestad2 stops$370
Nassau
Nassau1 stop$383
Kingston
Kingston2 stops$473
Simpson Bay
Simpson Bay2 stops$340
Providenciales
Providenciales1 stop$668
George Town
George Town2 stops$384
Willemstad
Willemstad2 stops$525
St. John's
St. John's2 stops$353
Aguadilla
Aguadilla1 stop$440

Cheap Flights from White Plains to Caribbean (HPN-0CB)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from White Plains to Caribbean 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 White Plains to Caribbean

Fri, Oct 3 - Tue, Oct 7
American Airlines Logo
5:25 pm - 12:45 pmHPN-SJU
19h 20m2 stops
American Airlines Logo
3:50 pm - 9:18 amSJU-HPN
17h 28m1 stop
$225American Airlines
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Mon, Jun 2 - Thu, Jun 5
JetBlue Logo
8:00 am - 11:45 amHPN-SJU
3h 45mnonstop
JetBlue Logo
5:20 pm - 9:30 pmSJU-HPN
4h 10mnonstop
$246JetBlue
Find Deal
Mon, Jun 16 - Fri, Jun 20
JetBlue Logo
8:00 am - 11:45 amHPN-SJU
3h 45mnonstop
JetBlue Logo
5:38 pm - 9:30 pmSJU-HPN
3h 52mnonstop
$254JetBlue
Find Deal
Fri, Sep 5 - Mon, Sep 8
American Airlines Logo
5:25 pm - 2:45 pmHPN-SJU
21h 20m2 stops
American Airlines Logo
3:55 pm - 11:17 amSJU-HPN
19h 22m2 stops
$309American Airlines
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Tue, Nov 4 - Tue, Nov 11
Delta Logo
6:00 am - 5:18 pmHPN-SJU
10h 18m1 stop
Delta Logo
3:28 pm - 9:38 pmSJU-HPN
7h 10m1 stop
$319Delta
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Tue, Jun 3 - Wed, Jun 11
Delta Logo
6:00 am - 4:04 pmHPN-NAS
10h 04m1 stop
Delta Logo
1:17 pm - 10:25 pmNAS-HPN
9h 08m1 stop
$383Delta
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Thu, Oct 9 - Mon, Oct 13
WestJet Logo
5:10 pm - 8:57 amHPN-PUJ
39h 47m2 stops
WestJet Logo
11:45 am - 11:46 amPUJ-HPN
24h 01m2 stops
$1,369WestJet
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Thu, Oct 16 - Sun, Oct 19
WestJet Logo
5:10 pm - 8:57 amHPN-PUJ
39h 47m2 stops
WestJet Logo
3:35 pm - 4:34 pmPUJ-HPN
24h 59m2 stops
$1,513WestJet
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Wed, Oct 22 - Mon, Oct 27
LATAM Airlines Logo
4:19 pm - 3:20 pmHPN-PUJ
23h 01m2 stops
LATAM Airlines Logo
5:35 pm - 12:11 pmPUJ-HPN
18h 36m2 stops
$2,254LATAM Airlines
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Thu, Aug 21 - Mon, Aug 25
LATAM Airlines Logo
6:40 pm - 5:35 pmHPN-PUJ
22h 55m2 stops
LATAM Airlines Logo
5:35 pm - 12:00 pmPUJ-HPN
18h 25m2 stops
$2,324LATAM Airlines
Find Deal
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KAYAK's insights & trends for White Plains to Caribbean flights

Get data-powered insights and trends into flights from White Plains to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest White Plains to Caribbean flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from White Plains to Caribbean.

The cheapest ticket to Caribbean from White Plains found in the last 72 hours was to San Juan, at $244 round-trip. The most popular route is from White Plains (HPN) 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 $244.

Can I save money by flying with a layover from White Plains to Caribbean?

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 $344, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from White Plains to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from White Plains to Caribbean, 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 White Plains to Caribbean is January, when tickets cost $311 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $537 and $503 respectively.

What’s the cheapest day of the week to fly from White Plains to Caribbean?

The average price of all round-trip flights from White Plains to Caribbean clicked on KAYAK for each day over the last 12 months.

When flying from White Plains to Caribbean, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to White Plains, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

How far in advance should I book a flight from White Plains to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from White Plains to Caribbean, 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 the flight from White Plains to Caribbean, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.


Good to know

Low seasonOctober
High seasonFebruary
Cheapest flight$119
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from White Plains to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from White Plains to Caribbean?

    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 White Plains to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from White Plains to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from White Plains to Caribbean 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 White Plains to Caribbean?

    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 White Plains to Caribbean 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 White Plains to Caribbean?

    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 White Plains to Caribbean 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?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $171 on average. Morning departures are around 17% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $511.

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from White Plains to the following destinations at these prices or less: San Juan $148 one-way - $322 round-trip

Top 3 airlines serving from White Plains to Caribbean

Need help choosing which airline to fly with from White Plains to Caribbean? 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.
7.3
JetBlueOverall score based on 2928 reviews
7.3Entertainment
7.6Comfort
8.0Crew
7.5Boarding
6.7Food
Airline reviews

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.

10.0 ExcellentAnonymous, Apr 2025LGA - FLL
Read more JetBlue reviews

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.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

In-flight staff was very helpful and excellent. However, the flight was delayed by 90 minutes. Also the boarding process should be expedited in case of delayed flights. This will help the passengers trying to make international connections.

Kayak sent over to jet blue my account being Mike Callaghan instead of Michael. I have a jet blue account with Michael that was connected

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

Delays on all NY flights. There was no communication on why but they didn’t say it was weather. Other carriers were not delayed.

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

They cancelled our flight without warning OR a refund. Never doing business with American Airlines again! This is the second AA booked trip in a row that we've had challenges with.

I got bumped due to weight restrictions even tho there were empty seats on my flight. I got put on an other flight with a stopover. My flight that originally was going to take 5-6 hours ever up being 14+ hours and my luggage arrived to my destination without me because I was made to check in my luggage on my original flight when I was deemed ok to board only to be asked to deplane. Worst flight experience.

Flight cancelled. Added a day and a half to my travel. American Airlines DID put me in a hotel for two nights, but have not given any money back for any of this! I spent money on an apartment at my destination that I basically wasted because I could not arrive.

I was pleasantly surprised with an upgrade at boarding. I finally had a mostly gluten free food options and a very attentive attendant.

It was good. It’s been a long time since my wife and I fly any where and things have changed. Our trip was to see our new grandson. We fly economy and that was not good for my bad back. It was a quick flight but uncomfortable.

Staff at the gate were incredibly rude, hostile and threatening. Never fly American Airlines.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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