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Caribbean

$133+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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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 May 1, 2025.

Round-trip from

$246
(JetBlue)

One-way from

$133
(JetBlue)

Popular in

December

Cheapest in

March

Average price

$262
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).
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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 May 2025
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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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 5/76:30 amHPN - SJU
2 stops14h 03mAmerican Airlines
Sat 5/103:50 pmSJU - HPN
1 stop17h 39mAmerican Airlines
Deal found 4/30$225
This JetBlue deal was found by Cheapflights users on 5/1. 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.
Sun 5/188:00 amHPN - SJU
Nonstop3h 45mJetBlue
Fri 5/235:20 pmSJU - HPN
Nonstop4h 10mJetBlue
Deal found 5/1$246
This Delta deal was found by Cheapflights users on 5/1. 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 5/176:29 amHPN - SJU
1 stop6h 47mDelta
Tue 5/2012:50 pmSJU - HPN
1 stop9h 22mDelta
Deal found 5/1$285
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/266:32 pmHPN - AUA
2 stops21h 18mAmerican Airlines
Mon 6/24:50 pmAUA - HPN
2 stops20h 25mAmerican Airlines
Deal found 5/1$340
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 8/105:29 pmHPN - STT
2 stops17h 36mAmerican Airlines
Wed 8/2011:40 amSTT - HPN
2 stops22h 50mAmerican Airlines
Deal found 4/30$345
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 8/185:29 pmHPN - PUJ
2 stops19h 21mAmerican Airlines
Mon 8/251:50 pmPUJ - HPN
2 stops20h 40mAmerican Airlines
Deal found 4/30$354
This American Airlines deal was found by Cheapflights users on 4/30. 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 8/155:29 pmHPN - NAS
2 stops16h 23mAmerican Airlines
Fri 8/222:27 pmNAS - HPN
1 stop19h 02mAmerican Airlines
Deal found 4/30$367
This Delta deal was found by Cheapflights users on 4/30. 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.
Sun 5/116:00 amHPN - NAS
1 stop7h 55mDelta
Wed 5/141:13 pmNAS - HPN
1 stop8h 59mDelta
Deal found 4/30$383
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/176:00 amHPN - MBJ
1 stop8h 00mAmerican Airlines
Wed 5/2110:10 amMBJ - HPN
1 stop11h 37mAmerican Airlines
Deal found 5/1$390
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/98:00 amHPN - STT
1 stop7h 53mJetBlue
Fri 6/132:20 pmSTT - HPN
1 stop7h 10mJetBlue
Deal found 4/30$390
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/142:29 pmHPN - PSE
1 stop9h 30mJetBlue
Wed 5/215:09 amPSE - HPN
1 stop6h 50mJetBlue
Deal found 4/30$428
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/186:32 pmHPN - STI
2 stops20h 28mAmerican Airlines
Fri 5/303:50 pmSTI - HPN
2 stops19h 00mAmerican Airlines
Deal found 4/29$437

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 May 1, 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

Sun 5/18

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Fri 5/23

5:20 pm-9:30 pm

Nonstop4h 10m

$246

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Fri 5/16

5:07 pm-4:36 pm

2 stops23h 29m

San Juan Luis Munoz Marin Intl

Thu 5/22

6:10 am-8:16 pm

2 stops14h 06m

$260

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

Sat 8/23

12:59 pm-10:12 pm

1 stop9h 13m

San Juan Luis Munoz Marin Intl

Wed 8/27

2:39 pm-9:44 pm

1 stop7h 05m

$275

White PlainsOranjestad

HPN - AUA

HPNAUA

White Plains Westchester County

Mon 5/26

6:32 pm-3:50 pm

2 stops21h 18m

Oranjestad Reina Beatrix

Mon 6/2

4:50 pm-1:15 pm

2 stops20h 25m

$340

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Sun 8/10

5:29 pm-11:05 am

2 stops17h 36m

Saint Thomas Island Cyril E King

Wed 8/20

11:40 am-10:30 am

2 stops22h 50m

$345

White PlainsPunta Cana

HPN - PUJ

HPNPUJ

White Plains Westchester County

Mon 8/18

5:29 pm-12:50 pm

2 stops19h 21m

Punta Cana

Mon 8/25

1:50 pm-10:30 am

2 stops20h 40m

$354

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Fri 8/15

5:29 pm-9:52 am

2 stops16h 23m

Nassau Intl

Fri 8/22

2:27 pm-9:29 am

1 stop19h 02m

$367

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

Sun 5/11

6:00 am-1:55 pm

1 stop7h 55m

Nassau Intl

Wed 5/14

1:13 pm-10:12 pm

1 stop8h 59m

$383

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

Mon 6/9

8:00 am-3:53 pm

1 stop7h 53m

Saint Thomas Island Cyril E King

Fri 6/13

2:20 pm-9:30 pm

1 stop7h 10m

$390

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sat 5/17

6:00 am-1:00 pm

1 stop8h 00m

Montego Bay Sangster Intl

Wed 5/21

10:10 am-10:47 pm

1 stop11h 37m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 December is currently the most expensive (average of $336). 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 May 1, 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 May 1, 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).

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 May 1, 2025.
Delta
8.0
Very good
7,934 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

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
1,767 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

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
2,923 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

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
7,934 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

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
2,826 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

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.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $133. However, be on the lookout for offers from American Airlines and Delta, 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 December is currently the most expensive (average of $336). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$191FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$543FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$272Average$578FlexibilityNo cancel feeOn-time71%

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