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Caribbean

$89+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/11. 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.
Wed 11/196:30 amHPN - SJU
2 stops16h 22mAmerican Airlines
Fri 12/58:20 amSJU - HPN
2 stops12h 46mAmerican Airlines
Deal found 11/11$200
This JetBlue deal was found by Cheapflights users on 11/11. 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 11/188:00 amHPN - SJU
Nonstop3h 51mJetBlue
Fri 11/215:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 11/11$216
This Trip.com deal was found by Cheapflights users on 11/13. 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.
Tue 12/28:00 amHPN - SJU
Nonstop3h 51mJetBlue
Tue 12/912:30 pmSJU - HPN
1 stop8h 00mJetBlue
Deal found 11/13$230
This Delta deal was found by Cheapflights users on 11/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:00 amHPN - SJU
1 stop10h 26mDelta
Wed 11/197:00 amSJU - HPN
1 stop12h 01mDelta
Deal found 11/13$231
This Trip.com deal was found by Cheapflights users on 11/13. 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.
Mon 12/88:00 amHPN - SJU
Nonstop3h 51mJetBlue
Wed 12/105:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 11/13$234
This Trip.com deal was found by Cheapflights users on 11/10. 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.
Thu 12/118:00 amHPN - SJU
Nonstop3h 51mJetBlue
Thu 12/115:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 11/10$235
This American Airlines deal was found by Cheapflights users on 11/11. 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 11/167:59 amHPN - SJU
1 stop6h 55mAmerican Airlines
Tue 11/186:00 amSJU - HPN
2 stops15h 10mAmerican Airlines
Deal found 11/11$240
This Priceline deal was found by Cheapflights users on 11/11. 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.
Wed 11/198:00 amHPN - SJU
Nonstop3h 51mJetBlue
Fri 12/55:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 11/11$251
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/156:30 amHPN - SJU
2 stops13h 54mAmerican Airlines
Mon 11/176:25 amSJU - HPN
2 stops14h 45mAmerican Airlines
Deal found 11/12$265
This JetBlue deal was found by Cheapflights users on 11/13. 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.
Tue 12/168:00 amHPN - SJU
Nonstop3h 51mJetBlue
Tue 12/234:12 pmSJU - HPN
Nonstop4h 17mJetBlue
Deal found 11/13$266
This Trip.com deal was found by Cheapflights users on 11/12. 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.
Sun 11/168:00 amHPN - SJU
Nonstop3h 51mJetBlue
Tue 11/186:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 11/12$270
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/136:49 pmHPN - PUJ
2 stops16h 06mAmerican Airlines
Wed 12/175:16 pmPUJ - HPN
1 stop17h 13mAmerican Airlines
Deal found 11/12$302

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 November 13, 2025.

Round-trip from

$200
(American Airlines)

One-way from

$89
(Delta)

Popular in

December

Cheapest in

March

Average price

$285

Good round-trip deal

$244 or less

Good one-way deal

$276 or less
From White Plains Westchester County to Caribbean
Search Deals
One-way flight from White Plains Westchester County to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from White Plains Westchester County to Caribbean.
Search Deals
Price to beat on a one-way flight from White Plains Westchester County to Caribbean.
Search Deals

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 November 13, 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

Sat 11/22

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Sat 11/29

5:55 pm-9:00 pm

Nonstop4h 05m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Thu 1/22

8:45 am-1:31 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:15 pm-9:30 pm

Nonstop4h 15m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/21

8:45 am-1:31 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:15 pm-9:30 pm

Nonstop4h 15m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sun 1/25

10:29 am-8:57 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:30 am-6:00 pm

1 stop11h 30m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Fri 1/23

12:59 pm-11:44 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:30 am-6:00 pm

1 stop11h 30m

$225

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Thu 1/22

8:45 am-1:31 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Mon 1/26

6:15 pm-9:30 pm

Nonstop4h 15m

$231

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/21

8:15 am-3:30 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:15 pm-9:30 pm

Nonstop4h 15m

$245

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/21

8:45 am-1:31 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Sat 1/24

5:00 pm-11:00 pm

1 stop7h 00m

$245

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/21

8:15 am-3:30 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:15 pm-9:30 pm

Nonstop4h 15m

$245

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 1/24

2:59 pm-10:44 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Mon 1/26

6:15 pm-9:30 pm

Nonstop4h 15m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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, March is the cheapest month in which you can book a flight from White Plains to Caribbean (average of $79). Flying from White Plains to Caribbean in August is currently the most expensive (average of $138). 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 November 13, 2025.

When flying from White Plains to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 35% versus a flight in the morning.

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 November 13, 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 November 13, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and JetBlue 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.
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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
11,050 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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
7.2
Good
2,907 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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.
Frontier
5.8
Fair
3,114 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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. 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.

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

    A quick flight from White Plains to Caribbean can take about 3h 51m. JetBlue provides one of the quickest options available for as low as $216. The distance between White Plains and Caribbean is about 1627 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $89. However, be on the lookout for offers from American Airlines and JetBlue, 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 - Saint Thomas Island Cyril E King or White Plains Westchester County - Oranjestad Reina Beatrix.

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

    The cheapest flight price from White Plains to Caribbean is $153. On average you can expect to pay $319. The most popular route, (White Plains Westchester County - San Juan Luis Munoz Marin Intl), can usually be booked for $177.

  • 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, March is the cheapest month in which you can book a flight from White Plains to Caribbean (average of $79). Flying from White Plains to Caribbean in August is currently the most expensive (average of $138). 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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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

Discover the top 4 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$224FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$377FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$205Average$557FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$224Average$548FlexibilityNo cancel feeOn-time71%

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