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$133+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$246
(JetBlue)

One-way from

$133
(JetBlue)

Popular in

December

Cheapest in

March

Average price

$262

Good round-trip deal

$294 or less

Good one-way deal

$228 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 May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 5/76:30 amHPN - SJU
2 stops14h 03mAmerican Airlines
Sat 5/103:50 pmSJU - HPN
1 stop17h 39mAmerican Airlines
Deal found 4/30$225
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/138:00 amHPN - SJU
Nonstop3h 45mJetBlue
Wed 6/115:20 pmSJU - HPN
Nonstop4h 10mJetBlue
Deal found 4/29$246
This American Airlines deal was found by Cheapflights users on 4/30. 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 8/105:29 pmHPN - STT
2 stops17h 36mAmerican Airlines
Wed 8/2011:40 amSTT - HPN
2 stops22h 50mAmerican Airlines
Deal found 4/30$345
This American Airlines deal was found by Cheapflights users on 4/30. 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 8/186:59 pmHPN - PUJ
1 stop17h 11mAmerican Airlines
Mon 8/251:50 pmPUJ - HPN
2 stops20h 40mAmerican Airlines
Deal found 4/30$354
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.
Fri 8/155:29 pmHPN - NAS
2 stops16h 11mAmerican Airlines
Fri 8/222:27 pmNAS - HPN
1 stop19h 02mAmerican Airlines
Deal found 4/29$367
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/145:07 pmHPN - AUA
2 stops22h 43mAmerican Airlines
Tue 5/202:45 pmAUA - HPN
2 stops20h 05mAmerican Airlines
Deal found 4/30$371
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/116:00 amHPN - NAS
1 stop10h 04mDelta
Wed 5/142:15 pmNAS - HPN
1 stop7h 57mDelta
Deal found 4/29$383
This JetBlue deal was found by Cheapflights users on 4/30. 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 6/98:00 amHPN - STT
1 stop7h 53mJetBlue
Fri 6/132:20 pmSTT - HPN
1 stop7h 10mJetBlue
Deal found 4/30$390
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/97:53 pmHPN - MBJ
2 stops18h 02mAmerican Airlines
Sun 9/143:05 pmMBJ - HPN
2 stops19h 12mAmerican Airlines
Deal found 4/30$404
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 8/153:15 pmHPN - SJU
1 stop6h 57mDelta
Tue 8/197:30 amSJU - HPN
1 stop10h 44mDelta
Deal found 4/30$411
This JetBlue deal was found by Cheapflights users on 4/30. 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 5/142:29 pmHPN - PSE
1 stop9h 30mJetBlue
Wed 5/215:09 amPSE - HPN
1 stop6h 50mJetBlue
Deal found 4/30$428
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.
Sun 5/186:32 pmHPN - STI
2 stops20h 28mAmerican Airlines
Fri 5/303:50 pmSTI - HPN
2 stops19h 00mAmerican Airlines
Deal found 4/29$437

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 May 1, 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

Tue 5/13

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 6/11

5:20 pm-9:30 pm

Nonstop4h 10m

$246

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Thu 5/15

1:45 pm-8:33 pm

1 stop6h 48m

San Juan Luis Munoz Marin Intl

Thu 5/22

6:10 am-8:16 pm

2 stops14h 06m

$260

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 6/17

12:49 pm-10:48 pm

1 stop9h 59m

San Juan Luis Munoz Marin Intl

Thu 6/26

6:15 am-4:35 pm

1 stop10h 20m

$275

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Sun 8/10

5:29 pm-11:05 am

2 stops17h 36m

Saint Thomas Island Cyril E King

Wed 8/20

11:40 am-10:30 am

2 stops22h 50m

$345

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Mon 8/18

6:59 pm-12:10 pm

1 stop17h 11m

Punta Cana

Mon 8/25

1:50 pm-10:30 am

2 stops20h 40m

$354

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Fri 8/15

5:29 pm-9:40 am

2 stops16h 11m

Nassau Intl

Fri 8/22

2:27 pm-9:29 am

1 stop19h 02m

$367

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

Wed 5/14

5:07 pm-3:50 pm

2 stops22h 43m

Oranjestad Reina Beatrix

Tue 5/20

2:45 pm-10:50 am

2 stops20h 05m

$371

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Sun 5/11

6:00 am-4:04 pm

1 stop10h 04m

Nassau Intl

Wed 5/14

2:15 pm-10:12 pm

1 stop7h 57m

$383

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Mon 6/9

8:00 am-3:53 pm

1 stop7h 53m

Saint Thomas Island Cyril E King

Fri 6/13

2:20 pm-9:30 pm

1 stop7h 10m

$390

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Tue 9/9

7:53 pm-12:55 pm

2 stops18h 02m

Montego Bay Sangster Intl

Sun 9/14

3:05 pm-11:17 am

2 stops19h 12m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 59 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 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 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 May 1, 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 May 1, 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).

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 May 1, 2025.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
2,924 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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. 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 $133. 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 - Montego Bay Sangster Intl or White Plains Westchester County - Kingston Norman Manley.

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

    The cheapest flight price from White Plains to Caribbean is $128. On average you can expect to pay $356. The most popular route, (White Plains Westchester County - San Juan Luis Munoz Marin Intl), can usually be booked for $236.

  • 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 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

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$191FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$543FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$272Average$578FlexibilityNo cancel feeOn-time71%

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