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Caribbean Islands

$99+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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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 February 20, 2025.

Round-trip from

$216
(JetBlue)

One-way from

$99
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$327
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. 5% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
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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 February 20, 2025.

This JetBlue deal was found by Cheapflights users on 2/20. 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.
Fri 4/188:00 amHPN - SJU
Nonstop3h 45mJetBlue
Wed 4/235:05 pmSJU - HPN
Nonstop3h 58mJetBlue
Deal found 2/20$216
This JetBlue deal was found by Cheapflights users on 2/20. 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.
Fri 3/288:00 amHPN - STT
1 stop7h 41mJetBlue
Wed 4/23:26 pmSTT - HPN
1 stop7h 07mJetBlue
Deal found 2/20$247
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Mon 2/2411:15 amHPN - SJU
2 stops11h 40mAmerican Airlines
Wed 2/266:00 amSJU - HPN
2 stops9h 37mAmerican Airlines
Deal found 2/20$255
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/108:00 amHPN - STT
2 stops26h 01mMultiple Airlines
Wed 3/1911:11 amSTT - HPN
2 stops25h 19mMultiple Airlines
Deal found 2/19$281
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/312:00 pmHPN - SJU
2 stops27h 27mMultiple Airlines
Thu 3/67:15 amSJU - HPN
2 stops30h 15mMultiple Airlines
Deal found 2/19$286
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 4/17:59 amHPN - AUA
1 stop8h 01mAmerican Airlines
Tue 4/85:05 pmAUA - HPN
2 stops18h 22mAmerican Airlines
Deal found 2/19$292
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Mon 3/106:35 pmHPN - NAS
1 stop15h 25mAmerican Airlines
Thu 3/1312:00 pmNAS - HPN
1 stop8h 16mAmerican Airlines
Deal found 2/20$315
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 2/277:59 amHPN - PUJ
1 stop6h 39mAmerican Airlines
Thu 3/64:40 pmPUJ - HPN
1 stop17h 49mAmerican Airlines
Deal found 2/20$331
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 3/275:03 pmHPN - MBJ
2 stops17h 32mAmerican Airlines
Tue 4/112:35 pmMBJ - HPN
1 stop9h 12mAmerican Airlines
Deal found 2/20$339
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 3/94:30 pmHPN - STI
2 stops20h 51mAmerican Airlines
Thu 3/202:11 pmSTI - HPN
2 stops21h 18mAmerican Airlines
Deal found 2/20$355
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 3/66:30 amHPN - SDQ
2 stops16h 18mAmerican Airlines
Sat 3/153:58 pmSDQ - HPN
2 stops19h 31mAmerican Airlines
Deal found 2/20$371
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 4/206:33 pmHPN - PLS
1 stop15h 42mAmerican Airlines
Thu 4/241:35 pmPLS - HPN
1 stop9h 27mAmerican Airlines
Deal found 2/20$386

Find flights from White Plains to Caribbean Islands within your budget

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 February 20, 2025.

Fly from

White Plains

Fly to

Caribbean Islands

Route

Depart

Return

Price

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Fri 4/18

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 4/23

5:05 pm-9:03 pm

Nonstop3h 58m

$216

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Fri 3/28

8:00 am-3:41 pm

1 stop7h 41m

Saint Thomas Island Cyril E King

Wed 4/2

3:26 pm-10:33 pm

1 stop7h 07m

$247

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 2/24

11:15 am-11:55 pm

2 stops11h 40m

San Juan Luis Munoz Marin Intl

Wed 2/26

6:00 am-2:37 pm

2 stops9h 37m

$255

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Mon 3/10

8:00 am-10:01 am

2 stops26h 01m

Saint Thomas Island Cyril E King

Wed 3/19

11:11 am-12:30 pm

2 stops25h 19m

$281

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 3/3

12:00 pm-4:27 pm

2 stops27h 27m

San Juan Luis Munoz Marin Intl

Wed 3/5

4:38 am-12:30 pm

2 stops32h 52m

$286

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

Tue 4/1

6:35 pm-3:35 pm

2 stops21h 00m

Oranjestad Reina Beatrix

Tue 4/8

5:05 pm-11:27 am

2 stops18h 22m

$292

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Mon 3/10

6:35 pm-10:00 am

1 stop15h 25m

Nassau Intl

Thu 3/13

12:00 pm-8:16 pm

1 stop8h 16m

$315

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Thu 3/27

5:03 pm-9:35 am

2 stops17h 32m

Montego Bay Sangster Intl

Tue 4/1

12:35 pm-10:47 pm

1 stop9h 12m

$339

White PlainsSantiago de los Caballeros

HPN - STI

HPNSTI

White Plains Westchester County

Sun 3/9

4:30 pm-1:21 pm

2 stops20h 51m

Santiago de los Caballeros

Thu 3/20

2:11 pm-11:29 am

2 stops21h 18m

$355

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Mon 4/7

6:33 pm-10:30 am

1 stop15h 57m

Punta Cana

Mon 4/14

2:15 pm-10:42 am

2 stops20h 27m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 59 results
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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.

Travel insights for flights from White Plains to Caribbean Islands

Get recent, data-driven insights about flights from White Plains to Caribbean Islands including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 20, 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 February 20, 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
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
1,795 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
7.4
Good
3,070 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
2,801 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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?

    $99 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $129 and $221, 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 - Oranjestad Reina Beatrix or White Plains Westchester County - Montego Bay Sangster Intl 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 $99. While the most popular route (White Plains Westchester County - San Juan Luis Munoz Marin Intl) can be booked for $198 on average our data indicates $361 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 March is currently the most expensive (average of $363). 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

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Alternative routes for White Plains to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from White Plains to Caribbean Islands

Discover the top 4 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$228FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$206Average$512FlexibilityNo cancel feeOn-time62%
DeltaCheapest$248Average$539FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$272Average$552FlexibilityNo cancel feeOn-time71%
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