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Caribbean

$99+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
oct. 10 — oct. 171
vie. 10/10
vie. 10/17
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 septiembre 10, 2025.

Round-trip from

$205
(American Airlines)

One-way from

$99
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$235
From Westchester County to Caribbean
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One-way flight from Westchester County to Caribbean
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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 ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 10, 2025.

This American Airlines deal was found by Cheapflights users on 9/8. 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.
jue. 10/25:29 pmHPN - SJU
2 stops17h 42mAmerican Airlines
lun. 10/65:00 pmSJU - HPN
2 stops17h 34mAmerican Airlines
Deal found 9/8$205
This Trip.com deal was found by Cheapflights users on 9/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/88:00 amHPN - SJU
Nonstop3h 48mJetBlue
dom. 10/125:01 pmSJU - HPN
Nonstop4h 00mJetBlue
Deal found 9/10$211
This JetBlue deal was found by Cheapflights users on 9/8. 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.
mar. 9/308:00 amHPN - SJU
Nonstop3h 45mJetBlue
lun. 10/65:01 pmSJU - HPN
Nonstop4h 00mJetBlue
Deal found 9/8$216
This Trip.com deal was found by Cheapflights users on 9/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/88:00 amHPN - SJU
Nonstop3h 43mJetBlue
jue. 12/112:00 pmSJU - HPN
1 stop9h 27mJetBlue
Deal found 9/10$217
This American Airlines deal was found by Cheapflights users on 9/8. 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.
lun. 9/225:29 pmHPN - SJU
2 stops17h 42mAmerican Airlines
mar. 9/304:43 pmSJU - HPN
2 stops16h 39mAmerican Airlines
Deal found 9/8$225
This JetBlue deal was found by Cheapflights users on 9/8. 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.
jue. 10/308:00 amHPN - SJU
Nonstop3h 51mJetBlue
lun. 11/36:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 9/8$230
This JetBlue deal was found by Cheapflights users on 9/8. 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.
mié. 9/178:00 amHPN - SJU
Nonstop3h 45mJetBlue
lun. 9/225:01 pmSJU - HPN
Nonstop4h 02mJetBlue
Deal found 9/8$231
This American Airlines deal was found by Cheapflights users on 9/8. 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.
vie. 10/36:30 amHPN - SJU
2 stops17h 07mAmerican Airlines
mar. 10/77:45 amSJU - HPN
2 stops15h 44mAmerican Airlines
Deal found 9/8$235
This JetBlue deal was found by Cheapflights users on 9/9. 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.
dom. 9/218:00 amHPN - SJU
Nonstop3h 45mJetBlue
mar. 9/235:00 pmSJU - HPN
Nonstop3h 59mJetBlue
Deal found 9/9$236
This Priceline deal was found by Cheapflights users on 9/8. 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.
vie. 10/38:00 amHPN - SJU
Nonstop3h 45mJetBlue
mar. 10/78:50 amSJU - HPN
1 stop13h 56mJetBlue
Deal found 9/8$237
This JetBlue deal was found by Cheapflights users on 9/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/98:00 amHPN - SJU
Nonstop3h 43mJetBlue
mié. 11/125:00 pmSJU - HPN
Nonstop4h 11mJetBlue
Deal found 9/10$244
This JetBlue deal was found by Cheapflights users on 9/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/83:59 pmHPN - SJU
1 stop7h 42mJetBlue
sáb. 10/185:01 pmSJU - HPN
Nonstop4h 00mJetBlue
Deal found 9/10$245

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 septiembre 10, 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

sáb. 10/4

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

dom. 10/5

5:01 pm-9:00 pm

Nonstop3h 59m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

jue. 10/2

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

mar. 10/7

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mié. 10/1

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

dom. 10/5

5:01 pm-9:00 pm

Nonstop3h 59m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

jue. 10/2

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

lun. 10/6

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mié. 10/1

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

mar. 10/7

5:01 pm-9:01 pm

Nonstop4h 00m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

lun. 9/22

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

lun. 9/22

5:01 pm-9:03 pm

Nonstop4h 02m

$231

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

jue. 10/2

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

sáb. 10/4

5:01 pm-9:00 pm

Nonstop3h 59m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mié. 10/8

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

jue. 10/9

5:01 pm-9:01 pm

Nonstop4h 00m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

lun. 9/22

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

mar. 9/23

5:00 pm-8:59 pm

Nonstop3h 59m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

dom. 11/2

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

jue. 11/6

5:00 pm-8:11 pm

Nonstop4h 11m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

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, 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 septiembre 10, 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 septiembre 10, 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 septiembre 10, 2025.
Read reviews from past customers who have flown American Airlines, JetBlue, and Frontier 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.
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
JetBlue
7.2
Good
2,913 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
Frontier
5.8
Fair
3,181 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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.

  • 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 $118. 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 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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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 septiembre 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$200FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$560FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$207Average$582FlexibilityNo cancel feeOn-time62%

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