$119 Find Cheap Flights from White Plains to Caribbean Islands - Compare and Save

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 8/3. 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$360
Santo Domingo
Santo Domingo2 stops$443
Montego Bay
Montego Bay1 stop$324
Oranjestad
Oranjestad2 stops$376
Nassau
Nassau1 stop$336
Kingston
Kingston1 stop$499
Simpson Bay
Simpson Bay2 stops$382
Providenciales
Providenciales1 stop$400
George Town
George Town1 stop$341
Willemstad
Willemstad2 stops$635
Aguadilla
Aguadilla1 stop$468
St. John's
St. John's2 stops$480
Punta Cana
Punta Cana1 stop$360
Santo Domingo
Santo Domingo2 stops$443
Montego Bay
Montego Bay1 stop$324
Oranjestad
Oranjestad2 stops$376
Nassau
Nassau1 stop$336
Kingston
Kingston1 stop$499
Simpson Bay
Simpson Bay2 stops$382
Providenciales
Providenciales1 stop$400
George Town
George Town1 stop$341
Willemstad
Willemstad2 stops$635
Aguadilla
Aguadilla1 stop$468
St. John's
St. John's2 stops$480

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

Tue, Sep 8 - Fri, Sep 18
JetBlue Logo
8:30 am - 5:33 pm
HPN
-
MBJ
10h 03m
1 stop
JetBlue Logo
1:15 pm - 10:57 pm
MBJ
-
HPN
8h 42m
1 stop
$324JetBlue
Mon, Jul 27 - Sat, Aug 1
American Airlines Logo
6:59 pm - 10:01 am
HPN
-
NAS
15h 02m
1 stop
American Airlines Logo
12:29 pm - 9:57 pm
NAS
-
HPN
9h 28m
1 stop
$336American Airlines
Mon, Aug 10 - Mon, Aug 17
American Airlines Logo
6:51 pm - 9:30 am
HPN
-
NAS
14h 39m
2 stops
American Airlines Logo
6:45 pm - 10:30 am
NAS
-
HPN
15h 45m
2 stops
$340American Airlines
Tue, Nov 10 - Tue, Nov 17
Delta Logo
6:00 am - 12:25 pm
HPN
-
GCM
6h 25m
1 stop
Delta Logo
1:50 pm - 9:36 pm
GCM
-
HPN
7h 46m
1 stop
$341Delta
Sat, Aug 15 - Fri, Aug 21
American Airlines Logo
11:00 am - 9:55 pm
HPN
-
SJU
10h 55m
2 stops
American Airlines Logo
3:47 pm - 9:29 am
SJU
-
HPN
17h 42m
1 stop
$341American Airlines
Sat, Aug 22 - Tue, Aug 25
American Airlines Logo
6:51 pm - 1:32 pm
HPN
-
NAS
18h 41m
1 stop
American Airlines Logo
7:45 am - 8:29 pm
NAS
-
HPN
12h 44m
2 stops
$348American Airlines
Sat, Aug 15 - Tue, Aug 18
American Airlines Logo
5:36 pm - 11:00 am
HPN
-
GCM
18h 24m
2 stops
American Airlines Logo
2:10 pm - 11:29 am
GCM
-
HPN
20h 19m
2 stops
$348American Airlines
Tue, Aug 4 - Thu, Aug 13
JetBlue Logo
8:30 am - 1:50 pm
HPN
-
NAS
5h 20m
1 stop
JetBlue Logo
2:47 pm - 10:44 pm
NAS
-
HPN
7h 57m
1 stop
$349JetBlue
Mon, Aug 24 - Fri, Aug 28
American Airlines Logo
6:30 am - 6:30 pm
HPN
-
SJU
12h 00m
2 stops
American Airlines Logo
3:47 pm - 9:29 am
SJU
-
HPN
17h 42m
1 stop
$351American Airlines
Sun, Aug 30 - Fri, Sep 4
Delta Logo
6:00 am - 1:25 pm
HPN
-
PUJ
7h 25m
1 stop
Delta Logo
1:10 pm - 10:21 pm
PUJ
-
HPN
9h 11m
1 stop
$360Delta
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 5 days was to San Juan, at $365 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 5 days was $365.

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

The average price for all round-trip flights from White Plains to Caribbean Islands 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 Islands is generally in the morning, when round-trip flights cost $421 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 $421.

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 $419, 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 February, when tickets cost $321 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $791 and $595 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 Thursday. 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 seasonMay
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 11% lower on average.
Flight from White Plains to George Town

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.

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 $218 one-way - $415 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.
7.1
American AirlinesOverall score based on 11779 reviews
6.8Entertainment
7.5Boarding
7.9Crew
7.2Comfort
6.4Food
Airline reviews

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

2.0 MediocreSophie, Jun 2026
LGA - ORD
Read more American Airlines reviews

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

Maybe focus more on delivering a good product vs selling me a damn credit card

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Their computers were down upon arrival to the airport. They were unable to figure out how to board us. We were delayed over an hour and a half.

Free wifi kept dropping so no inflight entertainment. And only snack option was cookies.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

Domestic flights are good. Just stay away from international travel

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

Since we started at syr the service, crews, and flights were just excellent

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

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

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

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.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

No WiFi No TV Bag of chips I guess it could be worse.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports