$103 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 from White Plains to Caribbean Islands departing on 3/1. 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

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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Flight Deals

Cheap Flights from White Plains to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$303
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay2 stops$305
Oranjestad
Oranjestad1 stop$299
Nassau
Nassau1 stop$330
Kingston
Kingston1 stop$426
Simpson Bay
Simpson Bay1 stop$327
Providenciales
Providenciales1 stop$346
Port of Spain
Port of Spain2 stops$487
George Town
George Town1 stop$325
Willemstad
Willemstad2 stops$247
St. John's
St. John's2 stops$415
Aguadilla
Aguadilla1 stop$372
Punta Cana
Punta Cana1 stop$303
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay2 stops$305
Oranjestad
Oranjestad1 stop$299
Nassau
Nassau1 stop$330
Kingston
Kingston1 stop$426
Simpson Bay
Simpson Bay1 stop$327
Providenciales
Providenciales1 stop$346
Port of Spain
Port of Spain2 stops$487
George Town
George Town1 stop$325
Willemstad
Willemstad2 stops$247
St. John's
St. John's2 stops$415
Aguadilla
Aguadilla1 stop$372

Book Cheap White Plains to Caribbean Islands 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 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

Mon, Feb 23 - Fri, Feb 27
American Airlines Logo
11:28 am - 9:49 pm
HPN
-
SJU
9h 21m
2 stops
American Airlines Logo
8:40 am - 6:19 pm
SJU
-
HPN
10h 39m
2 stops
$226American Airlines
Sun, Mar 8 - Wed, Mar 18
American Airlines Logo
6:54 pm - 11:06 am
HPN
-
STT
16h 12m
1 stop
American Airlines Logo
3:40 pm - 10:59 am
STT
-
HPN
19h 19m
2 stops
$240American Airlines
Mon, Mar 9 - Thu, Mar 12
American Airlines Logo
7:00 am - 10:58 pm
HPN
-
SJU
15h 58m
1 stop
American Airlines Logo
5:00 am - 6:24 pm
SJU
-
HPN
13h 24m
2 stops
$246American Airlines
Sun, Feb 22 - Thu, Feb 26
American Airlines Logo
5:30 pm - 12:12 pm
HPN
-
STT
17h 42m
2 stops
American Airlines Logo
5:42 pm - 10:58 am
STT
-
HPN
18h 16m
2 stops
$251American Airlines
Mon, Apr 27 - Thu, Apr 30
JetBlue Logo
8:30 am - 12:20 pm
HPN
-
SJU
3h 50mnonstop
JetBlue Logo
3:55 pm - 8:00 pm
SJU
-
HPN
4h 05mnonstop
$264JetBlue
Tue, Apr 7 - Fri, Apr 24
JetBlue Logo
8:40 am - 12:30 pm
HPN
-
SJU
3h 50mnonstop
JetBlue Logo
3:55 pm - 8:00 pm
SJU
-
HPN
4h 05mnonstop
$265JetBlue
Sat, Feb 28 - Thu, Mar 5
JetBlue Logo
8:00 am - 12:47 pm
HPN
-
SJU
3h 47mnonstop
JetBlue Logo
6:05 am - 1:34 pm
SJU
-
HPN
8h 29m
1 stop
$270JetBlue
Mon, Mar 9 - Tue, Mar 17
Delta Logo
10:27 am - 8:18 pm
HPN
-
SJU
9h 51m
1 stop
Delta Logo
6:15 am - 2:29 pm
SJU
-
HPN
8h 14m
1 stop
$274Delta
Mon, Mar 2 - Sat, Mar 7
Delta Logo
6:00 am - 2:50 pm
HPN
-
SXM
7h 50m
1 stop
Delta Logo
5:25 pm - 8:44 am
SXM
-
HPN
16h 19m
1 stop
$335Delta
Sun, Feb 22 - Thu, Mar 5
Delta Logo
6:00 am - 4:41 pm
HPN
-
PUJ
9h 41m
1 stop
Delta Logo
6:06 pm - 9:43 am
PUJ
-
HPN
16h 37m
1 stop
$339Delta
Booking Insights

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?

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

The cheapest ticket to Caribbean Islands from White Plains found in the last 72 hours was to San Juan, at $221 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 $221.

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 $412, 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 October, when tickets cost $244 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $534 and $518 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 Monday and more expensive on a Saturday. On your return trip to White Plains, you should consider flying back on a Thursday, and avoid Mondays 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$103
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 14% 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 in the morning, when round-trip flights cost $374 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 $374.

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 $138 one-way - $291 round-trip

Reviews of the 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.
7.2
American AirlinesOverall score based on 11248 reviews
6.9Entertainment
8.0Crew
7.5Boarding
7.2Comfort
6.4Food
Airline reviews

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

6.0 GoodMatthew, Jan 2026
JFK - CLT
Read more American Airlines reviews

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

There were no TV screens - even in Business class. 5 delays, and only given $12 meal voucher! Terrible!

My seat tv didn’t work the whole trip. And the seat space is too small despite being seated at the front.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

Disliked having to wait a little longer to disembark from the plan when we landed in London

Food should be better quality. Video screens have poor resolution and the library of movies is poor. The other airlines are much better.

They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

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.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports