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$114+ Cheap flights from White Plains (HPN) to Caribbean

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from White Plains to Caribbean

Keep the following information in mind while searching for White Plains to Caribbean flight deals. Data was last updated August 14, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$114
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$328

Good round-trip deal

$304 or less

Good one-way deal

$152 or less
From White Plains Westchester County to Caribbean
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One-way flight from White Plains Westchester County to Caribbean
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from White Plains Westchester County to Caribbean.
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Price to beat on a one-way flight from White Plains Westchester County to Caribbean.
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Find flight deals from White Plains to Caribbean

Cheapest flights from White Plains to Caribbean
Explore the most affordable flight options available from White Plains to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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 9/227:42 amHPN - SJU
1 stop8h 10mAmerican Airlines
Tue 9/301:37 pmSJU - HPN
2 stops19h 45mAmerican Airlines
Deal found 8/14$225
This JetBlue deal was found by Cheapflights users on 8/13. 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 9/178:00 amHPN - SJU
Nonstop3h 45mJetBlue
Wed 9/245:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 8/13$244
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 11/157:59 amHPN - SJU
1 stop12h 33mAmerican Airlines
Wed 11/196:00 amSJU - HPN
2 stops13h 13mAmerican Airlines
Deal found 8/13$263
This JetBlue deal was found by Cheapflights users on 8/14. 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.
Mon 9/18:00 amHPN - SJU
Nonstop3h 45mJetBlue
Thu 9/45:01 pmSJU - HPN
Nonstop3h 59mJetBlue
Deal found 8/14$264
This Priceline deal was found by Cheapflights users on 8/13. 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.
Mon 9/158:55 pmHPN - SJU
1 stop16h 59mJetBlue
Mon 9/225:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 8/13$276
This JetBlue deal was found by Cheapflights users on 8/13. 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 10/248:00 amHPN - SJU
Nonstop3h 45mJetBlue
Mon 10/275:01 amSJU - HPN
1 stop6h 46mJetBlue
Deal found 8/13$277
This JetBlue deal was found by Cheapflights users on 8/13. 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 9/128:00 amHPN - SJU
Nonstop3h 45mJetBlue
Sun 9/145:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 8/13$284
This Priceline deal was found by Cheapflights users on 8/13. 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.
Sun 9/148:55 pmHPN - SJU
1 stop13h 14mJetBlue
Sat 9/205:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 8/13$285
This JetBlue deal was found by Cheapflights users on 8/13. 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 43mJetBlue
Fri 11/76:00 amSJU - HPN
1 stop6h 47mJetBlue
Deal found 8/13$286
This Trip.com deal was found by Cheapflights users on 8/14. 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.
Mon 9/228:00 amHPN - SJU
Nonstop3h 45mJetBlue
Sun 9/285:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 8/14$287
This Trip.com deal was found by Cheapflights users on 8/13. 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.
Sat 11/158:00 amHPN - SJU
Nonstop3h 43mJetBlue
Wed 11/195:00 pmSJU - HPN
Nonstop4h 11mJetBlue
Deal found 8/13$289
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 9/126:50 pmHPN - AUA
2 stops21h 00mAmerican Airlines
Fri 9/194:29 pmAUA - HPN
2 stops19h 00mAmerican Airlines
Deal found 8/13$300

Cheapflights Fare Finder

 
Customize your flight search to find flights from White Plains to Caribbean 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 August 14, 2025.
Use the filters below to find and compare flights from White Plains to Caribbean that are best for you.

Fly from

White Plains

Fly to

Caribbean

Route

Depart

Return

Price

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 9/22

7:42 am-3:52 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Sat 9/27

4:45 pm-10:36 am

2 stops17h 51m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 11/12

8:00 am-12:43 pm

Nonstop3h 43m

San Juan Luis Munoz Marin Intl

Tue 11/18

5:00 pm-8:11 pm

Nonstop4h 11m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 2/2

1:30 pm-8:50 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Wed 2/11

4:40 pm-9:21 am

1 stop17h 41m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/8

6:30 am-11:59 pm

2 stops17h 29m

San Juan Luis Munoz Marin Intl

Sat 10/18

7:10 am-6:20 pm

2 stops11h 10m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Thu 9/18

6:30 am-11:37 pm

2 stops17h 07m

San Juan Luis Munoz Marin Intl

Tue 9/23

3:55 pm-9:22 am

2 stops17h 27m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 9/22

5:29 pm-11:11 am

2 stops17h 42m

San Juan Luis Munoz Marin Intl

Tue 9/30

1:37 pm-9:22 am

2 stops19h 45m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 10/18

11:04 am-11:05 pm

2 stops12h 01m

San Juan Luis Munoz Marin Intl

Tue 10/21

7:00 am-6:20 pm

2 stops11h 20m

$225

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

Fri 9/12

6:50 pm-3:50 pm

2 stops21h 00m

Oranjestad Reina Beatrix

Fri 9/19

4:29 pm-11:29 am

2 stops19h 00m

$300

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Fri 9/12

6:50 pm-12:35 pm

2 stops17h 45m

Punta Cana

Fri 9/19

3:25 pm-9:22 am

2 stops17h 57m

$319

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Sat 9/27

7:42 am-2:25 pm

1 stop6h 43m

Punta Cana

Sat 10/4

12:08 pm-9:29 am

2 stops21h 21m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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Best time to book a flight from White Plains to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, September is the cheapest month in which you can book a flight from White Plains to Caribbean (average of $254). Flying from White Plains to Caribbean 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 CB?

Find hourly flight availability from White Plains to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from White Plains to Caribbean as you normally would.

Weekly flight availability from White Plains to Caribbean

Explore weekly flight availability from White Plains to Caribbean. 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 August 14, 2025.

The most flights from HPN to 0CB 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated August 14, 2025.
Get a feel of what it's like to fly with American Airlines, JetBlue, and Frontier from White Plains to Caribbean by reading reviews from past customers. 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

Crew

8.0

Food

6.5

Boarding

7.5

Comfort

7.2

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Food

6.5

Boarding

7.5

Comfort

7.2

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
JetBlue
7.2
Good
2,913 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Food

6.5

Boarding

7.5

Comfort

7.2

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
Frontier
5.8
Fair
3,217 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Food

6.5

Boarding

7.5

Comfort

7.2

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from White Plains to Caribbean. 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?

    White Plains Westchester County (HPN) is the airport you will fly out of if you book a flight from White Plains to Caribbean. It is only a 3.7 mi journey to Westchester County (HPN) from White Plains’s city center.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $114. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from White Plains to Caribbean for a low price.

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

    The most popular route from White Plains to Caribbean is White Plains Westchester County - San Juan Luis Munoz Marin Intl. You may also consider White Plains Westchester County - George Town Owen Roberts Intl or White Plains Westchester County - Punta Cana.

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

    The cheapest flight price from White Plains to Caribbean is $127. On average you can expect to pay $332. The most popular route, (White Plains Westchester County - San Juan Luis Munoz Marin Intl), can usually be booked for $205.

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

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

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

    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.

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

    Yes. Cheapflights offers flight deals from White Plains to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from White Plains to Caribbean (average of $254). Flying from White Plains to Caribbean 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

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

Discover the top 3 airlines that operate flights from White Plains to Caribbean. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$200FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$589FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$215Average$586FlexibilityNo cancel feeOn-time62%

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