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Caribbean

$79+ Cheap flights from Westchester County 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Westchester County to Caribbean

Cheapest flights from Westchester County to Caribbean
Explore the most affordable flight options available from Westchester County to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This JetBlue deal was found by Cheapflights users on 12/27. 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.
Tue 12/308:00 amHPN - SJU
Nonstop3h 52mJetBlue
Sat 1/34:12 pmSJU - HPN
Nonstop4h 17mJetBlue
Deal found 12/27$281
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:55 pmHPN - AUA
1 stop16h 35mDelta
Tue 12/301:45 pmAUA - HPN
1 stop9h 24mDelta
Deal found 12/26$366
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:55 pmHPN - AUA
2 stops22h 35mDelta
Sun 1/41:45 pmAUA - HPN
1 stop9h 24mDelta
Deal found 12/26$369
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:15 pmHPN - AUA
2 stops20h 15mDelta
Wed 12/314:35 pmAUA - HPN
2 stops20h 24mDelta
Deal found 12/26$370
This American Airlines deal was found by Cheapflights users on 12/28. 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.
Wed 12/316:30 amHPN - SJU
2 stops13h 41mAmerican Airlines
Thu 1/86:00 amSJU - HPN
1 stop17h 59mAmerican Airlines
Deal found 12/28$398
This JetBlue deal was found by Cheapflights users on 12/25. 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 12/308:00 amHPN - SJU
Nonstop3h 52mJetBlue
Fri 1/95:45 pmSJU - HPN
Nonstop4h 22mJetBlue
Deal found 12/25$411
This JetBlue deal was found by Cheapflights users on 12/27. 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.
Tue 12/308:00 amHPN - SJU
Nonstop3h 52mJetBlue
Tue 12/304:12 pmSJU - HPN
Nonstop4h 17mJetBlue
Deal found 12/27$415
This JetBlue deal was found by Cheapflights users on 12/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:30 amHPN - SJU
1 stop7h 14mJetBlue
Sat 1/34:12 pmSJU - HPN
Nonstop4h 17mJetBlue
Deal found 12/26$456
This American Airlines deal was found by Cheapflights users on 12/25. 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 12/3011:04 amHPN - SJU
2 stops11h 55mAmerican Airlines
Fri 1/98:20 amSJU - HPN
2 stops12h 48mAmerican Airlines
Deal found 12/25$457
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:55 pmHPN - AUA
1 stop16h 35mDelta
Fri 1/24:40 pmAUA - HPN
2 stops20h 20mDelta
Deal found 12/26$462
This CheapOair deal was found by Cheapflights users on 12/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:23 amHPN - SJU
2 stops13h 33mMultiple Airlines
Fri 1/24:12 pmSJU - HPN
Nonstop4h 17mMultiple Airlines
Deal found 12/26$481
This Priceline deal was found by Cheapflights users on 12/25. 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 12/318:00 amHPN - SJU
Nonstop3h 52mJetBlue
Thu 1/88:30 pmSJU - HPN
1 stop16h 25mJetBlue
Deal found 12/25$496

Find flight deals from Westchester County to Caribbean

Keep the following information in mind while searching for Westchester County to Caribbean flight deals. Data was last updated December 28, 2025.

Round-trip from

$206
(JetBlue)

One-way from

$79
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$365
From Westchester County to Caribbean
Search Deals
One-way flight from Westchester County to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County 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 December 28, 2025.
Use the filters below to find and compare flights from Westchester County to Caribbean that are best for you.

Fly from

Westchester County

Fly to

Caribbean

Route

Depart

Return

Price

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Mon 2/2

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Thu 2/5

5:45 pm-9:00 pm

Nonstop4h 15m

$206

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 1/31

10:00 am-11:56 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:00 am-5:00 pm

1 stop12h 00m

$215

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Sun 2/1

5:15 pm-1:10 pm

2 stops18h 55m

Saint Thomas Island Cyril E King

Fri 2/6

2:54 pm-10:59 pm

1 stop9h 05m

$219

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Sun 3/8

5:30 pm-11:12 am

1 stop17h 42m

Saint Thomas Island Cyril E King

Wed 3/18

5:37 pm-10:30 am

2 stops16h 53m

$219

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/28

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 2/4

5:45 pm-9:07 pm

Nonstop4h 22m

$241

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 1/28

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:45 pm-9:07 pm

Nonstop4h 22m

$241

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 1/10

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sun 1/11

5:45 pm-9:07 pm

Nonstop4h 22m

$246

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 2/3

8:40 am-1:25 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:15 pm-9:30 pm

Nonstop4h 15m

$256

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Sat 1/24

7:00 am-8:19 pm

1 stop13h 19m

Nassau Intl

Sat 1/31

10:55 am-5:00 pm

1 stop6h 05m

$265

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Tue 1/27

7:30 am-1:22 pm

1 stop5h 52m

Nassau Intl

Sat 1/31

12:09 pm-6:08 pm

1 stop5h 59m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 60 results
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Best time to book a flight from Westchester County to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Westchester County 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 Westchester County to Caribbean

What is the cheapest month to book a flight from Westchester County to Caribbean?

Currently, October is the cheapest month in which you can book a flight from Westchester County to Caribbean (average of $175). Flying from Westchester County to Caribbean in August is currently the most expensive (average of $327). 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 REU to CB?

Find hourly flight availability from Westchester County 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 December 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Westchester County to Caribbean as you normally would.

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 December 28, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from Westchester County to Caribbean. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,016 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

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
7.9
Good
8,016 reviews
Delta
7.9
Good
8,016 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

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
11,071 reviews
Delta
7.9
Good
8,016 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

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
7.2
Good
2,901 reviews
Delta
7.9
Good
8,016 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

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.
Frontier
5.8
Fair
3,064 reviews
Delta
7.9
Good
8,016 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

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 Westchester County to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Westchester County to Caribbean?

    Departing from Westchester County to Caribbean will take you 3h 45m. The distance from Westchester County to Caribbean is about 1627 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Westchester County to Caribbean that include hotel bookings?

    Yes. In addition to deals on Westchester County to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Caribbean.

  • Can I find deals for business class flights from Westchester County to Caribbean?

    Yes. Cheapflights offers flight deals from Westchester County 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 Westchester County to Caribbean?

    Currently, October is the cheapest month in which you can book a flight from Westchester County to Caribbean (average of $175). Flying from Westchester County to Caribbean in August is currently the most expensive (average of $327). 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 Westchester County to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Westchester County to Caribbean

Discover the top 4 airlines that operate flights from Westchester County 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$224FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$331FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$206Average$506FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$349Average$559FlexibilityNo cancel feeOn-time71%

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