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Caribbean

$91+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
nov. 26 — dic. 31
mié. 11/26
mié. 12/3
1 adult, Economy
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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 octubre 27, 2025.

This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/128:00 amHPN - SJU
Nonstop3h 51mJetBlue
mié. 11/196:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 10/26$200
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/158:00 amHPN - SJU
Nonstop3h 51mJetBlue
vie. 12/194:14 pmSJU - HPN
Nonstop4h 15mJetBlue
Deal found 10/25$204
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/45:16 pmHPN - SJU
2 stops16h 01mAmerican Airlines
jue. 11/68:00 amSJU - HPN
1 stop15h 47mAmerican Airlines
Deal found 10/27$215
This JetBlue deal was found by Cheapflights users on 10/27. 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.
dom. 11/98:00 amHPN - SJU
Nonstop3h 51mJetBlue
mié. 11/126:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 10/27$236
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/111:04 amHPN - SJU
2 stops12h 01mAmerican Airlines
jue. 11/611:13 amSJU - HPN
2 stops9h 57mAmerican Airlines
Deal found 10/27$240
This American Airlines deal was found by Cheapflights users on 10/25. 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.
vie. 10/316:30 amHPN - SJU
2 stops15h 40mAmerican Airlines
lun. 11/36:25 amSJU - HPN
2 stops14h 45mAmerican Airlines
Deal found 10/25$250
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/171:00 pmHPN - SJU
1 stop6h 18mJetBlue
dom. 11/235:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 10/26$259
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/168:00 amHPN - SJU
Nonstop3h 51mJetBlue
sáb. 11/225:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 10/26$260
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/208:00 amHPN - SJU
Nonstop3h 51mJetBlue
dom. 11/235:55 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 10/26$264
This JetBlue deal was found by Cheapflights users on 10/27. 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.
sáb. 11/18:30 amHPN - SJU
Nonstop3h 51mJetBlue
jue. 11/66:00 pmSJU - HPN
Nonstop4h 05mJetBlue
Deal found 10/27$271
This JetBlue deal was found by Cheapflights users on 10/27. 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.
lun. 11/107:00 amHPN - NAS
1 stop6h 17mJetBlue
mié. 11/122:22 pmNAS - HPN
1 stop7h 15mJetBlue
Deal found 10/27$289
This American Airlines deal was found by Cheapflights users on 10/25. 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.
mar. 12/97:30 amHPN - PUJ
1 stop7h 46mAmerican Airlines
mar. 12/165:16 pmPUJ - HPN
2 stops18h 36mAmerican Airlines
Deal found 10/25$302

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 octubre 27, 2025.

Round-trip from

$200
(Trip.com)

One-way from

$91
(JetBlue)

Popular in

December

Cheapest in

March

Average price

$218
From Westchester County to Caribbean
Search Deals
One-way flight from Westchester County to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 octubre 27, 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

lun. 11/10

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

sáb. 11/15

5:55 pm-9:00 pm

Nonstop4h 05m

$236

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mar. 11/18

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

vie. 11/21

5:55 pm-9:00 pm

Nonstop4h 05m

$240

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mié. 11/12

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

sáb. 11/22

5:55 pm-9:00 pm

Nonstop4h 05m

$240

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

dom. 2/1

2:59 pm-12:04 am

1 stop8h 05m

San Juan Luis Munoz Marin Intl

vie. 2/6

6:15 pm-9:30 pm

Nonstop4h 15m

$259

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mar. 2/3

2:59 pm-12:04 am

1 stop8h 05m

San Juan Luis Munoz Marin Intl

mar. 2/10

6:15 pm-9:30 pm

Nonstop4h 15m

$259

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mar. 2/24

7:00 am-5:55 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

jue. 3/5

5:00 pm-7:55 pm

Nonstop3h 55m

$259

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

mié. 2/25

2:29 pm-11:59 pm

1 stop8h 30m

San Juan Luis Munoz Marin Intl

mié. 3/4

5:00 pm-7:55 pm

Nonstop3h 55m

$259

White PlainsAguadilla

HPN - BQN

HPNBQN

White Plains Westchester County

sáb. 1/31

8:00 pm-3:30 am

1 stop6h 30m

Aguadilla Borinquen

dom. 2/8

5:05 am-1:59 pm

1 stop9h 54m

$260

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

dom. 2/22

8:00 am-1:00 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

vie. 2/27

5:00 pm-7:55 pm

Nonstop3h 55m

$264

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

dom. 2/1

2:59 pm-12:04 am

1 stop8h 05m

San Juan Luis Munoz Marin Intl

sáb. 2/7

5:00 pm-11:00 pm

1 stop7h 00m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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 octubre 27, 2025.

It’s typically best to fly out from Westchester County to Caribbean in the evening. Doing so could potentially save you 35% on the flight price compared to flying in the morning, which is usually more expensive.

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 octubre 27, 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
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

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
7,996 reviews
Delta
7.9
Good
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

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
11,031 reviews
Delta
7.9
Good
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

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
2,906 reviews
Delta
7.9
Good
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

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
3,123 reviews
Delta
7.9
Good
7,996 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

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 51m. 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 $91. 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, 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

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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 octubre 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$200FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$331FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$205Average$550FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$224Average$547FlexibilityNo cancel feeOn-time71%

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