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Caribbean Islands

$113+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$205
(Trip.com)

One-way from

$113
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$286
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. 9% potential increase in price ($28 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 July 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 July 31, 2025.

This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:00 amHPN - SJU
Nonstop3h 45mJetBlue
Mon 9/225:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 7/30$205
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/304:43 pmSJU - HPN
2 stops16h 39mAmerican Airlines
Deal found 7/31$225
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Mon 9/16:59 pmHPN - AUA
2 stops20h 51mAmerican Airlines
Mon 9/84:50 pmAUA - HPN
2 stops16h 32mAmerican Airlines
Deal found 7/29$300
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 10/106:59 pmHPN - PUJ
2 stops16h 37mAmerican Airlines
Mon 10/134:39 pmPUJ - HPN
2 stops20h 21mAmerican Airlines
Deal found 7/30$319
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/86:55 pmHPN - STT
1 stop15h 55mAmerican Airlines
Mon 10/1311:45 amSTT - HPN
2 stops22h 49mAmerican Airlines
Deal found 7/30$325
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 11/812:44 pmHPN - SJU
1 stop9h 15mDelta
Sat 11/157:30 amSJU - HPN
1 stop11h 37mDelta
Deal found 7/30$334
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/265:29 pmHPN - GCM
2 stops18h 41mAmerican Airlines
Fri 8/292:10 pmGCM - HPN
2 stops20h 18mAmerican Airlines
Deal found 7/30$336
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 9/137:42 amHPN - PLS
1 stop6h 42mAmerican Airlines
Sat 9/201:20 pmPLS - HPN
1 stop6h 40mAmerican Airlines
Deal found 7/30$348
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 8/266:54 pmHPN - NAS
1 stop15h 46mAmerican Airlines
Sat 8/302:36 pmNAS - HPN
2 stops19h 54mAmerican Airlines
Deal found 7/29$349
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/307:42 amHPN - SDQ
2 stops12h 48mAmerican Airlines
Sat 10/412:15 pmSDQ - HPN
2 stops21h 14mAmerican Airlines
Deal found 7/31$365
This JetBlue deal was found by Cheapflights users on 7/31. 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 9/158:00 amHPN - STT
1 stop6h 31mJetBlue
Mon 9/223:30 pmSTT - HPN
1 stop5h 33mJetBlue
Deal found 7/31$375
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/76:30 amHPN - MBJ
2 stops8h 08mAmerican Airlines
Thu 9/111:56 pmMBJ - HPN
2 stops18h 26mAmerican Airlines
Deal found 7/29$397

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 July 31, 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 9/19

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 9/22

5:01 pm-9:03 pm

Nonstop4h 02m

$205

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

Tue 9/30

4:43 pm-10:45 am

1 stop18h 02m

$225

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

Sat 9/13

6:50 pm-11:24 am

1 stop16h 34m

Oranjestad Reina Beatrix

Wed 9/17

4:29 pm-9:29 am

1 stop17h 00m

$295

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Fri 10/10

6:59 pm-11:36 am

2 stops16h 37m

Punta Cana

Mon 10/13

4:39 pm-1:00 pm

2 stops20h 21m

$319

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Wed 10/8

6:55 pm-10:50 am

1 stop15h 55m

Saint Thomas Island Cyril E King

Mon 10/13

11:45 am-10:34 am

2 stops22h 49m

$325

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 11/8

12:44 pm-10:59 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Sat 11/15

7:30 am-6:07 pm

1 stop11h 37m

$334

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 8/26

5:29 pm-11:10 am

2 stops18h 41m

George Town Owen Roberts Intl

Fri 8/29

2:10 pm-11:28 am

2 stops20h 18m

$336

White PlainsProvidenciales

HPN - PLS

HPNPLS

White Plains Westchester County

Sat 9/13

7:42 am-2:24 pm

1 stop6h 42m

Providenciales

Sat 9/20

1:20 pm-8:00 pm

1 stop6h 40m

$348

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Tue 8/26

6:54 pm-10:40 am

1 stop15h 46m

Nassau Intl

Sat 8/30

2:36 pm-10:30 am

2 stops19h 54m

$349

White PlainsSanto Domingo

HPN - SDQ

HPNSDQ

White Plains Westchester County

Tue 9/30

7:42 am-8:30 pm

2 stops12h 48m

Santo Domingo Las Americas

Sat 10/4

12:15 pm-9:29 am

2 stops21h 14m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 59 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 July 31, 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 July 31, 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 July 31, 2025.
Read reviews from past customers who have flown Delta, LATAM 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.
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

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
1,822 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

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
2,914 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

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
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

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
2,978 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

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 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.

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

    $113 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 $118 and $138, 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 - Punta Cana or White Plains Westchester County - Montego Bay Sangster Intl 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 $152. While the most popular route (White Plains Westchester County - San Juan Luis Munoz Marin Intl) can be booked for $205 on average our data indicates $314 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

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$200FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$588FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$214Average$574FlexibilityNo cancel feeOn-time62%

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