$83 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 from White Plains to Caribbean departing on 9/9. 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

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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$279
Santo Domingo
Santo Domingo2 stops$390
Montego Bay
Montego Bay1 stop$351
Oranjestad
Oranjestad2 stops$305
Nassau
Nassau1 stop$345
Kingston
Kingston2 stops$428
Simpson Bay
Simpson Bay2 stops$340
Providenciales
Providenciales2 stops$352
Port of Spain
Port of Spain2 stops$413
George Town
George Town2 stops$336
Willemstad
Willemstad1 stop$1,582
Aguadilla
Aguadilla1 stop$390
Punta Cana
Punta Cana2 stops$279
Santo Domingo
Santo Domingo2 stops$390
Montego Bay
Montego Bay1 stop$351
Oranjestad
Oranjestad2 stops$305
Nassau
Nassau1 stop$345
Kingston
Kingston2 stops$428
Simpson Bay
Simpson Bay2 stops$340
Providenciales
Providenciales2 stops$352
Port of Spain
Port of Spain2 stops$413
George Town
George Town2 stops$336
Willemstad
Willemstad1 stop$1,582
Aguadilla
Aguadilla1 stop$390

Cheap Flights from White Plains to Caribbean

 
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

Mon, Sep 22 - Tue, Sep 30
American Airlines Logo
5:29 pm - 11:11 amHPN-SJU
17h 42m2 stops
American Airlines Logo
4:43 pm - 9:22 amSJU-HPN
16h 39m2 stops
$145American Airlines
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Mon, Sep 22 - Tue, Sep 30
American Airlines Logo
5:29 pm - 11:11 amHPN-SJU
17h 42m2 stops
American Airlines Logo
4:43 pm - 9:22 amSJU-HPN
16h 39m2 stops
$165American Airlines
Find Deal
Fri, Sep 19 - Wed, Sep 24
JetBlue Logo
8:00 am - 11:45 amHPN-SJU
3h 45mnonstop
JetBlue Logo
5:00 pm - 8:57 pmSJU-HPN
3h 57mnonstop
$244JetBlue
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Sun, Jul 20 - Thu, Jul 24
JetBlue Logo
8:00 am - 11:45 amHPN-SJU
3h 45mnonstop
JetBlue Logo
5:38 pm - 9:30 pmSJU-HPN
3h 52mnonstop
$266JetBlue
Find Deal
Tue, Sep 16 - Fri, Sep 26
Delta Logo
6:00 am - 1:09 pmHPN-MBJ
8h 09m1 stop
Delta Logo
4:59 pm - 12:01 pmMBJ-HPN
18h 02m2 stops
$351Delta
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Wed, Sep 10 - Mon, Sep 15
Delta Logo
6:00 am - 1:34 pmHPN-NAS
7h 34m1 stop
Delta Logo
3:14 pm - 10:18 pmNAS-HPN
7h 04m1 stop
$382Delta
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Sun, Oct 5 - Wed, Oct 15
 Logo
12:09 pm - 9:44 amHPN-STT
21h 35m3 stops
 Logo
9:40 am - 12:39 pmSTT-HPN
26h 59m3 stops
Mon, Aug 25 - Fri, Aug 29
 Logo
1:23 pm - 11:27 amHPN-KIN
23h 04m3 stops
 Logo
6:25 pm - 3:49 pmKIN-HPN
20h 24m2 stops
Wed, Aug 13 - Sun, Aug 17
WestJet Logo
12:37 pm - 1:45 pmHPN-UVF
25h 08m2 stops
WestJet Logo
2:35 pm - 10:23 pmUVF-HPN
31h 48m2 stops
$3,281WestJet
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Fri, Aug 1 - Thu, Aug 7
WestJet Logo
12:46 pm - 1:45 pmHPN-UVF
48h 59m2 stops
WestJet Logo
2:35 pm - 10:24 pmUVF-HPN
31h 49m2 stops
$3,312WestJet
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 $340, 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 $305 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $515 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 5 weeks before departure.


Good to know

Low seasonOctober
High seasonFebruary
Cheapest flight$83
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 1% increase in price.
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 $209 one-way - $336 round-trip

Reviews of the top 4 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.
8.0
DeltaOverall score based on 7951 reviews
8.5Crew
7.3Food
7.9Comfort
8.2Boarding
7.9Entertainment
Airline reviews

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

6.0 GoodAnonymous, Jul 2025JFK - LAS
Read more Delta reviews

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

Overall, aside from the baggage issue, it was as good as one expects.

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Our bag was lost so that made unnecessary chaos On our trip

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

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.

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.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

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