HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$103+ Cheap flights from White Plains (HPN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from White Plains to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from White Plains to Caribbean Islands

Keep the following information in mind while searching for White Plains to Caribbean Islands flight deals. Data was last updated abril 29, 2025.

Round-trip from

$236
(JetBlue)

One-way from

$113
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$333
From White Plains Westchester County to Caribbean Islands
Search Deals
One-way flight from White Plains Westchester County to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from White Plains to Caribbean Islands

Cheapest flights from White Plains to Caribbean Islands
Explore the most affordable flight options available from White Plains to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/610:05 amHPN - SJU
1 stop10h 28mAmerican Airlines
mar. 5/136:10 amSJU - HPN
2 stops11h 52mAmerican Airlines
Deal found 4/29$225
This JetBlue deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/138:00 amHPN - SJU
Nonstop3h 45mJetBlue
mar. 5/205:20 pmSJU - HPN
Nonstop4h 10mJetBlue
Deal found 4/28$236
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/306:00 amHPN - STT
1 stop7h 39mDelta
mié. 10/82:42 pmSTT - HPN
1 stop6h 56mDelta
Deal found 4/28$305
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/105:29 pmHPN - STT
2 stops19h 23mAmerican Airlines
mié. 8/201:52 pmSTT - HPN
2 stops20h 38mAmerican Airlines
Deal found 4/28$345
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/296:32 pmHPN - PUJ
2 stops19h 03mAmerican Airlines
mié. 6/42:39 pmPUJ - HPN
2 stops18h 50mAmerican Airlines
Deal found 4/29$354
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/156:59 pmHPN - SDQ
2 stops18h 36mAmerican Airlines
mar. 6/177:10 pmSDQ - HPN
2 stops19h 30mAmerican Airlines
Deal found 4/28$355
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/208:27 amHPN - NAS
1 stop4h 58mAmerican Airlines
mié. 9/242:45 pmNAS - HPN
1 stop5h 28mAmerican Airlines
Deal found 4/28$355
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/147:59 amHPN - AUA
1 stop8h 11mAmerican Airlines
mar. 5/205:10 pmAUA - HPN
1 stop16h 19mAmerican Airlines
Deal found 4/29$365
This JetBlue deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/88:00 amHPN - STT
1 stop7h 53mJetBlue
vie. 6/132:20 pmSTT - HPN
1 stop7h 10mJetBlue
Deal found 4/28$370
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/266:00 amHPN - NAS
1 stop10h 04mDelta
jue. 5/292:15 pmNAS - HPN
1 stop7h 57mDelta
Deal found 4/27$373
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/85:16 pmHPN - GCM
2 stops18h 44mAmerican Airlines
sáb. 11/156:10 pmGCM - HPN
1 stop15h 08mAmerican Airlines
Deal found 4/28$384
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/136:59 pmHPN - MBJ
2 stops15h 32mAmerican Airlines
vie. 6/205:05 pmMBJ - HPN
2 stops19h 00mAmerican Airlines
Deal found 4/28$425

Cheapflights Fare Finder

Customize your flight search to find flights from White Plains to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 29, 2025.
Use the filters below to find and compare flights from White Plains to Caribbean Islands that are best for you.

Fly from

White Plains

Fly to

Caribbean Islands

Route

Depart

Return

Price

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mié. 5/14

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

jue. 5/22

5:20 pm-9:30 pm

Nonstop4h 10m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mié. 5/14

7:59 am-3:00 pm

1 stop7h 01m

San Juan Luis Munoz Marin Intl

mar. 5/20

6:30 am-10:50 am

2 stops28h 20m

$250

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

mar. 9/30

6:00 am-1:39 pm

1 stop7h 39m

Saint Thomas Island Cyril E King

mié. 10/8

2:42 pm-9:38 pm

1 stop6h 56m

$305

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

dom. 8/10

5:29 pm-12:52 pm

2 stops19h 23m

Saint Thomas Island Cyril E King

mié. 8/20

1:52 pm-10:30 am

2 stops20h 38m

$345

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

jue. 5/29

6:32 pm-1:35 pm

2 stops19h 03m

Punta Cana

mié. 6/4

2:39 pm-9:29 am

2 stops18h 50m

$354

White PlainsSanto Domingo

HPN - SDQ

HPNSDQ

White Plains Westchester County

dom. 6/15

6:59 pm-1:35 pm

2 stops18h 36m

Santo Domingo Las Americas

mar. 6/17

7:10 pm-2:40 pm

2 stops19h 30m

$355

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

mié. 5/14

7:59 am-4:10 pm

1 stop8h 11m

Oranjestad Reina Beatrix

mar. 5/20

5:10 pm-9:29 am

1 stop16h 19m

$365

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

dom. 6/8

8:00 am-3:53 pm

1 stop7h 53m

Saint Thomas Island Cyril E King

vie. 6/13

2:20 pm-9:30 pm

1 stop7h 10m

$370

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

lun. 5/26

6:00 am-4:04 pm

1 stop10h 04m

Nassau Intl

jue. 5/29

2:15 pm-10:12 pm

1 stop7h 57m

$373

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

jue. 6/12

5:29 pm-11:04 am

2 stops18h 35m

George Town Owen Roberts Intl

jue. 6/19

12:10 pm-10:35 am

2 stops21h 25m

$384

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from White Plains to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from White Plains with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from White Plains to Caribbean Islands

What is the cheapest month to book a flight from White Plains to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from White Plains to Caribbean Islands (average of $254). Flying from White Plains to Caribbean Islands in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HPN to EPX?

Find hourly flight availability from White Plains to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 29, 2025.

When flying from White Plains to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated abril 29, 2025.
To help decide which airline to fly from White Plains to Caribbean Islands, see what other customers have to say about Delta, LATAM Airlines and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
LATAM Airlines
7.5
Good
1,767 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
WestJet
7.2
Good
2,826 reviews
Delta
8.0
Very good
7,936 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from White Plains to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from White Plains to Caribbean Islands?

    White Plains Westchester County (HPN), located 3.7 mi from the city center, is the airport you fly out of when you book flights from White Plains to Caribbean Islands.

  • What are the cheapest airlines to fly from White Plains to Caribbean Islands one-way?

    $113 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on JetBlue and Delta, with prices starting from $128 and $133, respectively.

  • What are the most popular routes from White Plains to Caribbean Islands?

    When deciding which route to take from White Plains to Caribbean Islands consider White Plains Westchester County - San Juan Luis Munoz Marin Intl, White Plains Westchester County - Punta Cana or White Plains Westchester County - Oranjestad Reina Beatrix as they are the most popular.

  • What are the cheapest flights from White Plains to Caribbean Islands?

    Looking at all options, your cheapest flight can be booked for $128. While the most popular route (White Plains Westchester County - San Juan Luis Munoz Marin Intl) can be booked for $236 on average our data indicates $356 when flying from White Plains to Caribbean Islands.

  • Can I find deals for flights from White Plains to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on White Plains to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from White Plains to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from White Plains to Caribbean Islands.

  • Can I find deals for business class flights from White Plains to Caribbean Islands?

    Yes. Cheapflights offers flight deals from White Plains to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from White Plains to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from White Plains to Caribbean Islands (average of $254). Flying from White Plains to Caribbean Islands in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for White Plains to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Los Angeles flights
LaGuardia to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Dallas/Fort Worth flights
Newark to Fort Lauderdale flights
Newark to Cancún flights
Newark to Los Angeles flights
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Dallas/Fort Worth flights
Newark to Orlando flights
Newark to Las Vegas flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Las Vegas flights
LaGuardia to Miami flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to San Francisco flights
Newark to Seattle flights
John F Kennedy Intl to Seattle flights
John F Kennedy Intl to Orlando flights
Newark to Dallas/Fort Worth flights
Newark to Atlanta flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to Atlanta flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to Hobby flights
LaGuardia to Orlando flights
Newark to O'Hare Intl flights
LaGuardia to Los Angeles flights
Newark to San Francisco flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Mexico City flights
LaGuardia to Las Vegas flights
John F Kennedy Intl to Sky Harbor Intl flights
LaGuardia to Cancún flights
LaGuardia to Hobby flights
Newark to Denver flights
Newark to Hobby flights
Newark to Tampa flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
John F Kennedy Intl to West Palm Beach flights
LaGuardia to Denver flights
John F Kennedy Intl to George Bush Intcntl flights
LaGuardia to Seattle flights
John F Kennedy Intl to Honolulu flights
Newark to Sky Harbor Intl flights
John F Kennedy Intl to Charlotte flights
John F Kennedy Intl to Ontario flights
John F Kennedy Intl to Tampa flights
John F Kennedy Intl to Denver flights

Top 3 airlines flying from White Plains to Caribbean Islands

Discover the top 3 airlines that operate flights from White Plains to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$191FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$543FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$272Average$578FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.