$133 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 5/16. 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, 0 bags

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Cheap Flights from White Plains to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$357
Santo Domingo
Santo Domingo1 stop$386
Montego Bay
Montego Bay1 stop$337
Oranjestad
Oranjestad1 stop$366
Nassau
Nassau2 stops$382
Kingston
Kingston1 stop$517
Simpson Bay
Simpson Bay2 stops$372
Providenciales
Providenciales1 stop$425
Port of Spain
Port of Spain2 stops$354
George Town
George Town2 stops$318
Willemstad
Willemstad2 stops$555
Aguadilla
Aguadilla1 stop$437
St. John's
St. John's2 stops$471
Punta Cana
Punta Cana2 stops$357
Santo Domingo
Santo Domingo1 stop$386
Montego Bay
Montego Bay1 stop$337
Oranjestad
Oranjestad1 stop$366
Nassau
Nassau2 stops$382
Kingston
Kingston1 stop$517
Simpson Bay
Simpson Bay2 stops$372
Providenciales
Providenciales1 stop$425
Port of Spain
Port of Spain2 stops$354
George Town
George Town2 stops$318
Willemstad
Willemstad2 stops$555
Aguadilla
Aguadilla1 stop$437
St. John's
St. John's2 stops$471

Book Cheap White Plains to Caribbean Plane Tickets

 
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

Thu, May 7 - Mon, May 11
American Airlines Logo
6:00 am - 1:15 pm
HPN
-
STT
7h 15m
1 stop
American Airlines Logo
2:05 pm - 10:52 pm
STT
-
HPN
8h 47m
1 stop
$250American Airlines
Mon, Apr 27 - Wed, May 6
American Airlines Logo
6:59 pm - 12:07 pm
HPN
-
STT
17h 08m
1 stop
American Airlines Logo
2:30 pm - 10:30 am
STT
-
HPN
20h 00m
2 stops
$275American Airlines
Sun, May 10 - Sat, May 16
American Airlines Logo
6:30 am - 2:52 pm
HPN
-
SJU
8h 22m
2 stops
American Airlines Logo
3:44 pm - 10:52 pm
SJU
-
HPN
7h 08m
1 stop
$277American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
5:16 pm - 1:35 pm
HPN
-
STT
20h 19m
2 stops
American Airlines Logo
12:25 pm - 10:52 pm
STT
-
HPN
10h 27m
1 stop
$290American Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
5:16 pm - 11:35 am
HPN
-
STT
18h 19m
2 stops
American Airlines Logo
12:25 pm - 10:52 pm
STT
-
HPN
10h 27m
1 stop
$292American Airlines
Mon, Jun 1 - Fri, Jun 5
JetBlue Logo
8:00 am - 11:46 am
HPN
-
SJU
3h 46mnonstop
JetBlue Logo
5:56 pm - 10:00 pm
SJU
-
HPN
4h 04mnonstop
$347JetBlue
Sun, May 17 - Wed, May 20
JetBlue Logo
8:59 pm - 7:41 am
HPN
-
MBJ
11h 42m
1 stop
JetBlue Logo
8:41 am - 7:59 pm
MBJ
-
HPN
10h 18m
1 stop
$348JetBlue
Sun, May 10 - Wed, May 27
Multiple Airlines Logo
8:00 am - 3:12 pm
HPN
-
SJU
7h 12m
1 stop
Multiple Airlines Logo
6:41 pm - 8:59 pm
SJU
-
HPN
26h 18m
2 stops
$348Multiple Airlines
Sat, May 9 - Wed, May 13
Delta Logo
6:00 am - 3:34 pm
HPN
-
MBJ
10h 34m
1 stop
Delta Logo
4:59 pm - 9:48 am
MBJ
-
HPN
15h 49m
1 stop
$352Delta
Sat, May 9 - Wed, May 13
Delta Logo
5:15 pm - 11:53 am
HPN
-
MBJ
19h 38m
2 stops
Delta Logo
4:59 pm - 9:48 am
MBJ
-
HPN
15h 49m
1 stop
$357Delta
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from White Plains found in the last 72 hours was to San Juan, at $335 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 $335.

What is the cheapest time of day to fly to Caribbean?

The average price for all round-trip flights from White Plains to Caribbean 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 is generally in the morning, when round-trip flights cost $401 on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $401.

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 $570, 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 October, when tickets cost $238 (return) on average. On the other hand, the most expensive months are March and August, when the average cost of round-trip tickets is $565 and $561 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 Sunday and avoid Saturdays if you are looking for the best rates. For your return to White Plains, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonMay
Cheapest flight$133
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 5% 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.

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 $172 one-way - $443 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.
7.9
DeltaOverall score based on 8424 reviews
7.9Comfort
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

10.0 ExcellentAditi Sayan, Apr 2026
LGA - ATL
Read more Delta reviews

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

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!

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

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.

I am still at the Airport! Delayed Delayed and Delyaed

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

Not a pleasant experience, service was poor. Didn't like it

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

Wifi was spotty. Tray table was very dirty when I sat down.

Flight was extremely hot and they made us check our bags when the space was nowhere near full

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

For an international flight the seats were smaller than most flight I have been on in economy. I don’t know the size of the seats or perhaps it was the size of the seat dividers that made the seats feel smaller and little amount of space to even turn your body if you needed to

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports