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Caribbean Islands

$110+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sun 3/17:47 am
HPN
-
SJU
1 stop13h 02m
American Airlines
Thu 3/55:18 pm
SJU
-
HPN
1 stop17h 11m
American Airlines
Deal found 2/12$236
This American Airlines deal was found by Cheapflights users on 2/11. 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 3/86:54 pm
HPN
-
STT
1 stop16h 12m
American Airlines
Wed 3/184:42 pm
STT
-
HPN
1 stop16h 47m
American Airlines
Deal found 2/11$250
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Mon 2/236:30 am
HPN
-
SJU
2 stops8h 50m
American Airlines
Wed 2/258:00 am
SJU
-
HPN
2 stops11h 19m
American Airlines
Deal found 2/11$251
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Tue 3/311:28 am
HPN
-
SJU
2 stops8h 11m
American Airlines
Thu 3/58:40 am
SJU
-
HPN
2 stops12h 28m
American Airlines
Deal found 2/12$256
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Mon 3/911:29 am
HPN
-
SJU
2 stops12h 23m
American Airlines
Wed 3/186:00 am
SJU
-
HPN
1 stop17h 29m
American Airlines
Deal found 2/11$264
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
HPN
-
SJU
1 stop13h 50m
American Airlines
Tue 3/107:11 am
SJU
-
HPN
1 stop16h 18m
American Airlines
Deal found 2/10$271
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
HPN
-
STT
1 stop8h 04m
Delta
Fri 3/63:10 pm
STT
-
HPN
1 stop7h 50m
Delta
Deal found 2/12$271
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:30 am
HPN
-
SJU
Nonstop3h 50m
JetBlue
Fri 5/13:55 pm
SJU
-
HPN
Nonstop4h 05m
JetBlue
Deal found 2/11$274
This KAYAK deal was found by Cheapflights users on 2/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/228:30 am
HPN
-
SJU
Nonstop3h 47m
JetBlue
Thu 3/262:20 pm
SJU
-
HPN
Nonstop4h 15m
JetBlue
Deal found 2/10$275
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/211:28 am
HPN
-
SJU
2 stops9h 21m
American Airlines
Fri 3/67:00 am
SJU
-
HPN
1 stop17h 27m
American Airlines
Deal found 2/10$276
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
HPN
-
STT
1 stop7h 47m
Delta
Tue 3/2412:49 pm
STT
-
HPN
1 stop9h 18m
Delta
Deal found 2/11$280
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:48 pm
HPN
-
SJU
1 stop7h 36m
Delta
Tue 4/216:15 am
SJU
-
HPN
1 stop8h 14m
Delta
Deal found 2/12$284

Find 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 February 12, 2026.

Round-trip from

$236
(American Airlines)

One-way from

$110
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$299
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. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 12, 2026.
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 PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Wed 4/22

6:00 am-4:15 pm

1 stop10h 15m

Saint Thomas Island Cyril E King

Wed 4/29

1:15 pm-10:30 am

2 stops21h 15m

$250

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Wed 3/18

7:00 am-2:46 pm

1 stop7h 46m

Saint Thomas Island Cyril E King

Tue 3/24

4:20 pm-9:29 am

1 stop17h 09m

$250

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Sun 3/8

6:54 pm-11:06 am

1 stop16h 12m

Saint Thomas Island Cyril E King

Wed 3/18

3:40 pm-10:59 am

2 stops19h 19m

$250

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 2/28

11:28 am-12:52 am

2 stops12h 24m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:00 am-2:30 pm

2 stops8h 30m

$256

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Wed 3/18

6:00 am-2:45 pm

1 stop8h 45m

Saint Thomas Island Cyril E King

Wed 3/25

1:55 pm-10:07 pm

1 stop8h 12m

$280

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Tue 3/17

6:00 am-1:47 pm

1 stop7h 47m

Saint Thomas Island Cyril E King

Tue 3/24

12:49 pm-10:07 pm

1 stop9h 18m

$280

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Tue 3/17

6:00 am-2:45 pm

1 stop8h 45m

Saint Thomas Island Cyril E King

Wed 3/25

1:55 pm-10:07 pm

1 stop8h 12m

$280

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Wed 3/18

6:00 am-2:45 pm

1 stop8h 45m

Saint Thomas Island Cyril E King

Tue 3/24

12:49 pm-10:07 pm

1 stop9h 18m

$280

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 4/15

12:48 pm-8:24 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Tue 4/21

6:15 am-2:29 pm

1 stop8h 14m

$284

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Sun 2/22

6:00 am-3:04 pm

1 stop8h 04m

Saint Thomas Island Cyril E King

Thu 2/26

3:10 pm-10:00 pm

1 stop7h 50m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 60 results
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6

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, March is the cheapest month in which you can book a flight from White Plains to Caribbean Islands (average of $79). Flying from White Plains to Caribbean Islands 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 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 February 12, 2026.

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 February 12, 2026.

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 February 12, 2026.
Read reviews from past customers who have flown American 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.
American Airlines
7.2
Good
11,277 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,277 reviews
American Airlines
7.2
Good
11,277 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
JetBlue
7.2
Good
2,897 reviews
American Airlines
7.2
Good
11,277 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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.

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

    For as low as $284, American Airlines can have you in Caribbean Islands from White Plains in 7h 36m. The distance between White Plains and Caribbean Islands is about 1627 mi. This flight may include one or multiple stops.

  • 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 - Oranjestad Reina Beatrix or White Plains Westchester County - Punta Cana 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 $114. While the most popular route (White Plains Westchester County - San Juan Luis Munoz Marin Intl) can be booked for $274 on average, our data indicates $292 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, March is the cheapest month in which you can book a flight from White Plains to Caribbean Islands (average of $79). Flying from White Plains to Caribbean Islands 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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Top 4 airlines flying from White Plains to Caribbean Islands

Discover the top 4 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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$214FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$298FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$204Average$564FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$220Average$521FlexibilityNo cancel feeOn-time71%

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