$119 Find Cheap Flights from White Plains 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 $[0,preposition:'from ']$[0,article:'from ']$[0,place:'from'] $[1,preposition:'to ']$[1,article:'to ']$[1,place:'to'] departing on 8/23. 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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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 White Plains 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 White Plains to Caribbean Islands, as well as popular online travel agencies
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Flights Deals

Best Caribbean Islands 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$354
Santo Domingo
Santo Domingo2 stops$429
Montego Bay
Montego Bay1 stop$395
Oranjestad
Oranjestad2 stops$375
Nassau
Nassau1 stop$404
Kingston
Kingston1 stop$474
Simpson Bay
Simpson Bay2 stops$340
Providenciales
Providenciales2 stops$302
George Town
George Town1 stop$380
Willemstad
Willemstad2 stops$530
St. John's
St. John's2 stops$353
Aguadilla
Aguadilla1 stop$528
Punta Cana
Punta Cana2 stops$354
Santo Domingo
Santo Domingo2 stops$429
Montego Bay
Montego Bay1 stop$395
Oranjestad
Oranjestad2 stops$375
Nassau
Nassau1 stop$404
Kingston
Kingston1 stop$474
Simpson Bay
Simpson Bay2 stops$340
Providenciales
Providenciales2 stops$302
George Town
George Town1 stop$380
Willemstad
Willemstad2 stops$530
St. John's
St. John's2 stops$353
Aguadilla
Aguadilla1 stop$528

Cheap Flights from White Plains to Caribbean Islands (HPN-zzEPX)

 
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 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 White Plains to Caribbean Islands

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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Tue, Jun 3 - Tue, Jun 10
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
Wed, Jun 11 - Mon, Jun 16
JetBlue Logo
8:00 am - 11:45 amHPN-SJU
3h 45mnonstop
JetBlue Logo
5:38 pm - 9:30 pmSJU-HPN
3h 52mnonstop
$250JetBlue
Find Deal
Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
6:34 am - 8:10 pmHPN-SJU
13h 36m2 stops
American Airlines Logo
6:30 am - 11:17 pmSJU-HPN
16h 47m2 stops
$265American Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
Delta Logo
6:00 am - 2:23 pmHPN-SJU
7h 23m1 stop
Delta Logo
3:28 pm - 9:38 pmSJU-HPN
7h 10m1 stop
$319Delta
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Sat, Aug 30 - Sat, Sep 6
Delta Logo
6:00 am - 3:10 pmHPN-STT
9h 10m1 stop
Delta Logo
3:23 pm - 10:23 pmSTT-HPN
7h 00m1 stop
$339Delta
Find Deal
Fri, Jun 13 - Sat, Jun 21
WestJet Logo
3:04 pm - 10:48 amHPN-PUJ
19h 44m2 stops
WestJet Logo
9:55 am - 10:25 pmPUJ-HPN
36h 30m2 stops
$1,166WestJet
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Sat, Jun 14 - Sat, Jun 21
WestJet Logo
5:00 pm - 1:43 pmHPN-PUJ
44h 43m2 stops
WestJet Logo
9:55 am - 10:25 pmPUJ-HPN
36h 30m2 stops
$1,171WestJet
Find Deal
Wed, Jun 4 - Thu, Jan 22
LATAM Airlines Logo
6:54 pm - 3:20 pmHPN-PUJ
20h 26m2 stops
LATAM Airlines Logo
5:35 pm - 12:11 pmPUJ-HPN
19h 36m2 stops
$2,393LATAM Airlines
Find Deal
Sun, Jun 22 - Sat, Jun 28
LATAM Airlines Logo
6:44 pm - 3:20 pmHPN-PUJ
20h 36m2 stops
LATAM Airlines Logo
5:35 pm - 12:04 pmPUJ-HPN
18h 29m2 stops
$2,507LATAM Airlines
Find Deal
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KAYAK's insights & trends for White Plains to Caribbean Islands flights

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

What is the cheapest White Plains to Caribbean Islands 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 Islands.

The cheapest ticket to Caribbean Islands 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 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 $478, prices are generally cheapest when you fly direct.

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

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 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 White Plains to Caribbean Islands 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 Islands?

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

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Tuesday and more expensive on a Thursday. On your return trip to White Plains, you should consider flying back on a Thursday, and avoid Sundays for better deals.

How far in advance should I book a flight from White Plains 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 White Plains 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 the flight from White Plains to Caribbean Islands, 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 Islands flights

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

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

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

  • 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 airlines flying from White Plains to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from White Plains 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 White Plains 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.
7.3
JetBlueOverall score based on 2929 reviews
7.5Boarding
6.7Food
8.0Crew
7.6Comfort
7.3Entertainment
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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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