Caribbean

$78+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Jul 30 — Aug 61
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Cheap 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 July 25, 2025.

Round-trip from

$203
(Trip.com)

One-way from

$78
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$286
From Westchester County to Caribbean
One-way flight from Westchester County to Caribbean
Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in July 2025

Find 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 July 25, 2025.

This Trip.com deal was found by Cheapflights users on 7/24. 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.
Tue 9/28:00 amHPN - SJU
Nonstop3h 45mJetBlue
Thu 9/115:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 7/24$203
This American Airlines deal was found by Cheapflights users on 7/22. 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 11/111:04 amHPN - SJU
2 stops12h 01mAmerican Airlines
Tue 11/46:25 amSJU - HPN
2 stops12h 48mAmerican Airlines
Deal found 7/22$214
This Delta deal was found by Cheapflights users on 7/24. 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 9/306:00 amHPN - SJU
1 stop10h 31mDelta
Sat 10/42:26 pmSJU - HPN
1 stop7h 52mDelta
Deal found 7/24$275
This American Airlines deal was found by Cheapflights users on 7/23. 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 11/47:59 amHPN - PUJ
1 stop7h 25mAmerican Airlines
Sat 11/83:34 pmPUJ - HPN
2 stops18h 55mAmerican Airlines
Deal found 7/23$297
This American Airlines deal was found by Cheapflights users on 7/24. 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 9/16:30 amHPN - NAS
1 stop5h 23mAmerican Airlines
Wed 9/102:09 pmNAS - HPN
1 stop5h 51mAmerican Airlines
Deal found 7/24$306
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/15:29 pmHPN - STT
2 stops19h 21mAmerican Airlines
Fri 9/55:10 pmSTT - HPN
2 stops16h 12mAmerican Airlines
Deal found 7/22$325
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/66:50 pmHPN - SXM
2 stops18h 29mAmerican Airlines
Sat 9/132:20 pmSXM - HPN
2 stops20h 16mAmerican Airlines
Deal found 7/22$334
This American Airlines deal was found by Cheapflights users on 7/24. 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 9/215:29 pmHPN - AUA
2 stops21h 58mAmerican Airlines
Fri 9/262:50 pmAUA - HPN
2 stops18h 32mAmerican Airlines
Deal found 7/24$346
This Delta deal was found by Cheapflights users on 7/24. 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 8/206:00 amHPN - NAS
1 stop5h 48mDelta
Tue 8/263:00 pmNAS - HPN
1 stop7h 23mDelta
Deal found 7/24$349
This American Airlines deal was found by Cheapflights users on 7/24. 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 8/1911:00 amHPN - SDQ
2 stops9h 30mAmerican Airlines
Tue 8/267:05 amSDQ - HPN
2 stops16h 20mAmerican Airlines
Deal found 7/24$349
This JetBlue deal was found by Cheapflights users on 7/22. 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 9/18:00 amHPN - STT
1 stop5h 28mJetBlue
Fri 9/53:30 pmSTT - HPN
1 stop5h 30mJetBlue
Deal found 7/22$360
This Delta deal was found by Cheapflights users on 7/23. 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 9/16:00 amHPN - MBJ
1 stop10h 36mDelta
Wed 9/101:20 pmMBJ - HPN
1 stop8h 03mDelta
Deal found 7/23$371

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 July 25, 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

Tue 9/2

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Thu 9/11

5:01 pm-9:03 pm

Nonstop4h 02m

$203

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Wed 10/15

5:29 pm-11:06 am

2 stops17h 37m

San Juan Luis Munoz Marin Intl

Thu 10/23

5:30 am-11:28 pm

2 stops17h 58m

$269

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Tue 9/30

6:00 am-4:31 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Sat 10/4

2:26 pm-10:18 pm

1 stop7h 52m

$275

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Tue 11/4

7:59 am-4:24 pm

1 stop7h 25m

Punta Cana

Sat 11/8

3:34 pm-9:29 am

2 stops18h 55m

$297

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Mon 9/1

6:30 am-11:53 am

1 stop5h 23m

Nassau Intl

Wed 9/10

2:09 pm-8:00 pm

1 stop5h 51m

$306

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Mon 9/1

5:29 pm-12:50 pm

2 stops19h 21m

Saint Thomas Island Cyril E King

Fri 9/5

5:10 pm-9:22 am

2 stops16h 12m

$325

White PlainsSimpson Bay

HPN - SXM

HPNSXM

White Plains Westchester County

Sat 9/6

6:50 pm-1:19 pm

2 stops18h 29m

Simpson Bay Princess Juliana

Sat 9/13

2:20 pm-10:36 am

2 stops20h 16m

$334

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

Sun 1/18

6:40 pm-1:15 pm

1 stop17h 35m

Oranjestad Reina Beatrix

Thu 1/22

4:25 pm-9:50 am

1 stop18h 25m

$345

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

Sun 9/21

5:29 pm-3:27 pm

2 stops21h 58m

Oranjestad Reina Beatrix

Fri 9/26

2:50 pm-9:22 am

2 stops18h 32m

$346

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Wed 8/20

6:00 am-11:48 am

1 stop5h 48m

Nassau Intl

Tue 8/26

3:00 pm-10:23 pm

1 stop7h 23m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 59 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, September is the cheapest month in which you can book a flight from Westchester County to Caribbean (average of $254). Flying from Westchester County 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 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 July 25, 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.

Weekly flight availability from Westchester County to Caribbean

Explore weekly flight availability from Westchester County 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 July 25, 2025.

The most flights from zzREU 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 July 25, 2025.
Read reviews from past customers who have flown Delta, JetBlue, and American Airlines 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.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

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.
8.0
Very good
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

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.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

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.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

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.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

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.
  • What are the cheapest airlines to fly from Westchester County to Caribbean one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $78. However, be on the lookout for offers from Delta and JetBlue, as they are both options that can get you from Westchester County to Caribbean for a low price.

  • 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, September is the cheapest month in which you can book a flight from Westchester County to Caribbean (average of $254). Flying from Westchester County 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 Westchester County to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Westchester County to Caribbean

Discover the top 3 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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$200FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$213Average$599FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$224Average$570FlexibilityNo cancel feeOn-time71%

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