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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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
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 September 22, 2025.

Round-trip from

$211
(Trip.com)

One-way from

$99
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$246
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. 6% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 22, 2025.

This Trip.com deal was found by Cheapflights users on 9/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:00 amHPN - SJU
Nonstop3h 48mJetBlue
Tue 10/215:01 pmSJU - HPN
Nonstop4h 00mJetBlue
Deal found 9/21$211
This JetBlue deal was found by Cheapflights users on 9/21. 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.
Wed 10/18:00 amHPN - SJU
Nonstop3h 45mJetBlue
Sat 10/115:01 pmSJU - HPN
Nonstop4h 00mJetBlue
Deal found 9/21$216
This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:00 amHPN - SJU
Nonstop3h 48mJetBlue
Thu 10/95:01 pmSJU - HPN
Nonstop4h 00mJetBlue
Deal found 9/22$219
This JetBlue deal was found by Cheapflights users on 9/21. 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.
Tue 10/218:00 amHPN - SJU
Nonstop3h 48mJetBlue
Tue 10/286:00 amSJU - HPN
1 stop8h 06mJetBlue
Deal found 9/21$227
This Priceline deal was found by Cheapflights users on 9/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:00 amHPN - SJU
Nonstop3h 51mJetBlue
Sun 11/26:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/20$230
This Priceline deal was found by Cheapflights users on 9/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/188:00 amHPN - SJU
Nonstop3h 45mJetBlue
Sun 10/264:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/21$231
This Priceline deal was found by Cheapflights users on 9/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:55 pmHPN - SJU
1 stop23h 23mJetBlue
Sat 10/255:01 pmSJU - HPN
Nonstop3h 59mJetBlue
Deal found 9/20$234
This Priceline deal was found by Cheapflights users on 9/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/17:00 pmHPN - SJU
1 stop16h 35mJetBlue
Tue 11/412:30 pmSJU - HPN
1 stop10h 07mJetBlue
Deal found 9/20$237
This JetBlue deal was found by Cheapflights users on 9/20. 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.
Sun 11/98:00 amHPN - SJU
Nonstop3h 43mJetBlue
Wed 11/1212:30 pmSJU - HPN
1 stop10h 00mJetBlue
Deal found 9/20$241
This JetBlue deal was found by Cheapflights users on 9/21. 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 11/218:00 amHPN - SJU
Nonstop3h 51mJetBlue
Wed 11/266:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/21$244
This JetBlue deal was found by Cheapflights users on 9/21. 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.
Sun 10/268:00 amHPN - SJU
Nonstop3h 51mJetBlue
Fri 10/315:01 amSJU - HPN
1 stop6h 48mJetBlue
Deal found 9/21$245
This lastminute.com deal was found by Cheapflights users on 9/22. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:00 amHPN - NAS
1 stop6h 17mJetBlue
Mon 11/176:01 pmNAS - HPN
1 stop5h 26mJetBlue
Deal found 9/22$285

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 September 22, 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

Fri 10/3

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 10/7

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sun 10/5

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sat 10/18

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/8

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Sat 10/18

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 10/21

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Tue 10/28

4:05 am-2:06 pm

1 stop10h 01m

$227

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 10/18

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sat 10/25

12:35 pm-10:46 pm

1 stop10h 11m

$244

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sun 11/9

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Wed 11/12

6:00 pm-9:05 pm

Nonstop4h 05m

$244

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 1/12

8:45 am-1:31 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Fri 1/30

1:00 pm-10:30 pm

1 stop10h 30m

$259

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/28

7:30 am-6:35 pm

1 stop10h 05m

San Juan Luis Munoz Marin Intl

Mon 2/2

6:15 pm-9:30 pm

Nonstop4h 15m

$279

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 10/4

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sat 10/11

12:35 pm-10:46 pm

1 stop10h 11m

$298

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Tue 11/4

7:00 am-2:33 pm

1 stop6h 33m

Punta Cana

Fri 11/14

3:38 pm-11:27 pm

1 stop8h 49m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/20

Showing 1-10 of 60 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.

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 June is currently the most expensive (average of $339). 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 September 22, 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.

Weekly flight availability from White Plains to Caribbean Islands

Explore weekly flight availability from White Plains to Caribbean Islands. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 22, 2025.

The most flights from HPN to zzEPX are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 September 22, 2025.
Read reviews from past customers who have flown American Airlines and JetBlue from White Plains to Caribbean Islands. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
JetBlue
7.2
Good
2,911 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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.

  • How long is the flight from White Plains to Caribbean Islands?

    For as low as $216, JetBlue can have you in Caribbean Islands from White Plains in 3h 45m. The distance between White Plains and Caribbean Islands is about 1627 mi. This flight may include one or multiple stops.

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

    $118 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 $127 and $194, 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 - Montego Bay Sangster Intl or White Plains Westchester County - Punta Cana 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 $115. While the most popular route (White Plains Westchester County - San Juan Luis Munoz Marin Intl) can be booked for $211 on average, our data indicates $269 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 June is currently the most expensive (average of $339). 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 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 September 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$200FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$567FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$206Average$581FlexibilityNo cancel feeOn-time62%

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