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$81+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Round-trip from

$206
(American Airlines)

One-way from

$81
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$246

Good round-trip deal

$230 or less

Good one-way deal

$118 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. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% 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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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 September 29, 2025.

This American Airlines deal was found by Cheapflights users on 9/28. 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 10/253:00 pmHPN - SJU
2 stops8h 54mAmerican Airlines
Sat 11/15:30 amSJU - HPN
2 stops12h 50mAmerican Airlines
Deal found 9/28$213
This Trip.com deal was found by Cheapflights users on 9/27. 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 10/258:00 amHPN - SJU
Nonstop3h 45mJetBlue
Sat 11/14:05 amSJU - HPN
1 stop10h 01mJetBlue
Deal found 9/27$217
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/126:30 amHPN - SJU
2 stops17h 29mAmerican Airlines
Fri 10/171:35 pmSJU - HPN
2 stops20h 59mAmerican Airlines
Deal found 9/27$221
This JetBlue deal was found by Cheapflights users on 9/29. 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 10/148:00 amHPN - SJU
Nonstop3h 48mJetBlue
Tue 10/284:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/29$236
This Priceline deal was found by Cheapflights users on 9/26. 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 11/158:00 amHPN - SJU
Nonstop3h 51mJetBlue
Sat 11/225:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/26$240
This JetBlue deal was found by Cheapflights users on 9/27. 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 9/27$244
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/116:30 amHPN - SJU
2 stops17h 24mAmerican Airlines
Fri 10/171:35 pmSJU - HPN
2 stops20h 59mAmerican Airlines
Deal found 9/27$246
This Trip.com deal was found by Cheapflights users on 9/28. 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 11/108:00 amHPN - SJU
Nonstop3h 51mJetBlue
Tue 11/116:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/28$254
This JetBlue deal was found by Cheapflights users on 9/28. 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 11/47:00 amHPN - SJU
1 stop6h 36mJetBlue
Thu 11/612:30 pmSJU - HPN
1 stop10h 07mJetBlue
Deal found 9/28$256
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/244:30 pmHPN - AUA
2 stops18h 50mAmerican Airlines
Tue 10/282:45 pmAUA - HPN
2 stops20h 14mAmerican Airlines
Deal found 9/27$300
This JetBlue deal was found by Cheapflights users on 9/27. 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 11/177:00 amHPN - PUJ
1 stop6h 33mJetBlue
Sat 12/611:25 amPUJ - HPN
1 stop11h 35mJetBlue
Deal found 9/27$301
This American Airlines deal was found by Cheapflights users on 9/28. 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 12/45:19 pmHPN - PUJ
2 stops18h 34mAmerican Airlines
Mon 12/81:02 pmPUJ - HPN
1 stop9h 57mAmerican Airlines
Deal found 9/28$302

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 September 29, 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

Sun 10/5

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Thu 10/16

5:01 pm-9:01 pm

Nonstop4h 00m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 10/6

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 10/8

5:01 pm-9:01 pm

Nonstop4h 00m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 10/14

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Tue 10/28

4:55 pm-9:00 pm

Nonstop4h 05m

$236

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

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 11/11

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Tue 11/18

6:00 pm-9:05 pm

Nonstop4h 05m

$236

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

Fri 10/10

5:01 pm-9:01 pm

Nonstop4h 00m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/29

8:00 am-11:51 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Sun 11/2

6:00 pm-9:05 pm

Nonstop4h 05m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 10/28

8:00 am-11:51 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Tue 11/4

6:00 pm-9:05 pm

Nonstop4h 05m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/15

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Fri 10/17

5:01 pm-9:01 pm

Nonstop4h 00m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/15

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

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

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 September 29, 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 September 29, 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 September 29, 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

Overall

7.2

Comfort

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

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

Crew

8.0

Overall

7.2

Comfort

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

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
2,912 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Overall

7.2

Comfort

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
Frontier
5.8
Fair
3,157 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Overall

7.2

Comfort

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

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. 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 45m. JetBlue provides one of the quickest options available for as low as $236. The distance between White Plains and Caribbean is about 1627 mi. This flight may include one or multiple stops.

  • 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 - Punta Cana.

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

    The cheapest flight price from White Plains to Caribbean is $115. On average you can expect to pay $247. The most popular route, (White Plains Westchester County - San Juan Luis Munoz Marin Intl), can usually be booked for $200.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$200FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$571FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$206Average$581FlexibilityNo cancel feeOn-time62%

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