$99 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 9/14. 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

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 Cana2 stops$299
Santo Domingo
Santo Domingo2 stops$328
Montego Bay
Montego Bay1 stop$355
Oranjestad
Oranjestad2 stops$340
Nassau
Nassau1 stop$326
Simpson Bay
Simpson Bay2 stops$374
Kingston
Kingston1 stop$449
Providenciales
Providenciales1 stop$348
Port of Spain
Port of Spain2 stops$392
George Town
George Town2 stops$326
Willemstad
Willemstad2 stops$397
St. John's
St. John's2 stops$421
Aguadilla
Aguadilla1 stop$405
Punta Cana
Punta Cana2 stops$299
Santo Domingo
Santo Domingo2 stops$328
Montego Bay
Montego Bay1 stop$355
Oranjestad
Oranjestad2 stops$340
Nassau
Nassau1 stop$326
Simpson Bay
Simpson Bay2 stops$374
Kingston
Kingston1 stop$449
Providenciales
Providenciales1 stop$348
Port of Spain
Port of Spain2 stops$392
George Town
George Town2 stops$326
Willemstad
Willemstad2 stops$397
St. John's
St. John's2 stops$421
Aguadilla
Aguadilla1 stop$405

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

Thu, Sep 25 - Mon, Sep 29
JetBlue Logo
8:00 am - 11:45 amHPN-SJU
3h 45mnonstop
JetBlue Logo
5:01 pm - 9:03 pmSJU-HPN
4h 02mnonstop
$216JetBlue
Find Deal
Tue, Sep 23 - Sat, Oct 4
JetBlue Logo
8:00 am - 11:45 amHPN-SJU
3h 45mnonstop
JetBlue Logo
12:35 pm - 10:46 pmSJU-HPN
10h 11m1 stop
$228JetBlue
Find Deal
Mon, Oct 27 - Sat, Nov 1
JetBlue Logo
8:00 am - 11:51 amHPN-SJU
3h 51mnonstop
JetBlue Logo
4:55 pm - 9:00 pmSJU-HPN
4h 05mnonstop
$230JetBlue
Find Deal
Tue, Sep 23 - Tue, Sep 30
American Airlines Logo
5:29 pm - 12:47 pmHPN-SJU
19h 18m2 stops
American Airlines Logo
1:37 pm - 9:22 amSJU-HPN
19h 45m2 stops
$239American Airlines
Find Deal
Mon, Sep 22 - Tue, Sep 30
American Airlines Logo
5:29 pm - 11:11 amHPN-SJU
17h 42m2 stops
American Airlines Logo
1:37 pm - 9:22 amSJU-HPN
19h 45m2 stops
$261American Airlines
Find Deal
Thu, Dec 11 - Tue, Dec 16
Delta Logo
6:00 am - 5:23 pmHPN-SJU
10h 23m1 stop
Delta Logo
3:32 pm - 10:08 pmSJU-HPN
7h 36m1 stop
$275Delta
Find Deal
Mon, Jan 19 - Thu, Jan 22
Delta Logo
6:00 am - 3:54 pmHPN-STT
8h 54m1 stop
Delta Logo
3:00 pm - 9:36 pmSTT-HPN
7h 36m1 stop
$311Delta
Find Deal
Mon, Sep 15 - Thu, Sep 18
 Logo
9:18 am - 9:44 amHPN-STT
24h 26m3 stops
 Logo
10:49 am - 4:51 pmSTT-HPN
30h 02m3 stops
Fri, Oct 31 - Wed, Nov 5
WestJet Logo
12:45 pm - 5:24 pmHPN-MBJ
29h 39m2 stops
WestJet Logo
2:55 pm - 10:09 pmMBJ-HPN
31h 14m2 stops
$1,316WestJet
Find Deal
Fri, Dec 5 - Fri, Dec 12
WestJet Logo
12:44 pm - 6:24 pmHPN-MBJ
29h 40m2 stops
WestJet Logo
10:30 pm - 10:08 pmMBJ-HPN
23h 38m2 stops
$1,400WestJet
Find Deal
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 $201 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 $201.

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 $241 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $518 and $494 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, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$99
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 5% 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 $234 one-way - $238 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 10000 reviews
7.2Comfort
8.0Crew
6.5Food
6.9Entertainment
7.5Boarding
Airline reviews

We arrived 4 hours early and still almost missed the flight because they weren’t able to access one of the boarding tickets. They then sent hour bags late and we were all of our without clothing and eventually had to take an expensive cab back and forth to the airport as they wouldn’t deliver the bag which arrived late at night that day and we would have to wait until noon the began day (messing up a second day of plans). Also, all the food has dairy or pork. No vegan or even vegetarian option in the flight—even for purchase.

2.0 MediocreAnonymous, Aug 2025JFK - MAD
Read more American Airlines reviews

We arrived 4 hours early and still almost missed the flight because they weren’t able to access one of the boarding tickets. They then sent hour bags late and we were all of our without clothing and eventually had to take an expensive cab back and forth to the airport as they wouldn’t deliver the bag which arrived late at night that day and we would have to wait until noon the began day (messing up a second day of plans). Also, all the food has dairy or pork. No vegan or even vegetarian option in the flight—even for purchase.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

Pathetic check in experience at JFK. Everything is self check in. Not enough staff present to help with when the check in process or the kiosk gets stuck. Staff present not welcoming or pleasant at all. On the other hand the NY based flight crew was great. Courteous and friendly throughout the flight. Special meals leave a lot to be desired. Kids meals should be made available when kids are flying and same goes for special kids meals too.

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.

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.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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