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$84+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
mar. 8 — mar. 151
sáb. 3/8
sáb. 3/15
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 marzo 3, 2025.

Round-trip from

$216
(JetBlue)

One-way from

$84
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$253
From Westchester County to Caribbean
Search Deals
One-way flight from Westchester County to Caribbean
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($16 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 March 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 marzo 3, 2025.

This JetBlue deal was found by Cheapflights users on 3/2. 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. 5/38:00 amHPN - SJU
Nonstop3h 45mJetBlue
vie. 5/95:15 pmSJU - HPN
Nonstop4h 10mJetBlue
Deal found 3/2$216
This American Airlines deal was found by Cheapflights users on 3/1. 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.
mar. 3/411:15 amHPN - SJU
2 stops11h 40mAmerican Airlines
vie. 3/78:00 amSJU - HPN
1 stop16h 06mAmerican Airlines
Deal found 3/1$255
This Mytrip deal was found by Cheapflights users on 3/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/712:00 pmHPN - SJU
3 stops28h 34mMultiple Airlines
jue. 4/102:40 pmSJU - HPN
2 stops21h 50mMultiple Airlines
Deal found 3/2$325
This American Airlines deal was found by Cheapflights users on 3/2. 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.
mié. 3/126:30 amHPN - SDQ
2 stops16h 21mAmerican Airlines
mar. 3/186:30 amSDQ - HPN
2 stops15h 22mAmerican Airlines
Deal found 3/2$335
This American Airlines deal was found by Cheapflights users on 3/2. 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.
dom. 11/25:16 pmHPN - STT
2 stops17h 29mAmerican Airlines
vie. 11/76:15 pmSTT - HPN
2 stops21h 48mAmerican Airlines
Deal found 3/2$339
This American Airlines deal was found by Cheapflights users on 3/2. 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. 3/246:35 pmHPN - PLS
1 stop15h 55mAmerican Airlines
mié. 3/261:30 pmPLS - HPN
1 stop9h 36mAmerican Airlines
Deal found 3/2$346
This Delta deal was found by Cheapflights users on 3/3. 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.
lun. 3/176:00 amHPN - STT
1 stop7h 41mDelta
mar. 3/181:55 pmSTT - HPN
1 stop8h 20mDelta
Deal found 3/3$346
This Delta deal was found by Cheapflights users on 3/2. 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.
lun. 4/286:00 amHPN - NAS
1 stop10h 00mDelta
mié. 4/303:09 pmNAS - HPN
1 stop7h 09mDelta
Deal found 3/2$351
This American Airlines deal was found by Cheapflights users on 3/2. 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. 4/196:33 pmHPN - MBJ
1 stop15h 37mAmerican Airlines
mié. 4/2312:55 pmMBJ - HPN
2 stops20h 47mAmerican Airlines
Deal found 3/2$355
This American Airlines deal was found by Cheapflights users on 3/2. 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. 3/176:35 pmHPN - NAS
1 stop15h 25mAmerican Airlines
lun. 3/242:24 pmNAS - HPN
1 stop7h 28mAmerican Airlines
Deal found 3/2$355
This American Airlines deal was found by Cheapflights users on 3/1. 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.
mié. 5/146:32 pmHPN - AUA
1 stop16h 57mAmerican Airlines
mar. 5/205:01 pmAUA - HPN
1 stop16h 28mAmerican Airlines
Deal found 3/1$377
This Mytrip deal was found by Cheapflights users on 3/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/18:20 amHPN - PUJ
3 stops27h 57mMultiple Airlines
lun. 4/73:47 pmPUJ - HPN
2 stops28h 43mMultiple Airlines
Deal found 3/2$383

Find flights from Westchester County to Caribbean within your budget

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 marzo 3, 2025.

Fly from

Westchester County

Fly to

Caribbean

Route

Depart

Return

Price

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

sáb. 5/3

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

mar. 5/13

5:15 pm-9:25 pm

Nonstop4h 10m

$216

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

dom. 3/16

11:27 am-11:40 pm

2 stops12h 13m

San Juan Luis Munoz Marin Intl

mié. 3/19

7:25 am-8:16 pm

2 stops12h 51m

$305

White PlainsSan Juan

HPN - SJU

HPNSJU

White Plains Westchester County

lun. 4/7

12:00 pm-4:34 pm

3 stops28h 34m

San Juan Luis Munoz Marin Intl

jue. 4/10

2:40 pm-12:30 pm

2 stops21h 50m

$325

White PlainsSanto Domingo

HPN - SDQ

HPNSDQ

White Plains Westchester County

mar. 3/18

6:30 am-10:51 pm

2 stops16h 21m

Santo Domingo Las Americas

jue. 3/27

5:00 am-10:47 pm

2 stops17h 47m

$335

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

lun. 7/21

5:29 pm-3:57 pm

2 stops22h 28m

Saint Thomas Island Cyril E King

jue. 7/24

4:00 pm-10:58 am

2 stops18h 58m

$339

White PlainsSaint Thomas Island

HPN - STT

HPNSTT

White Plains Westchester County

lun. 3/17

6:00 am-1:41 pm

1 stop7h 41m

Saint Thomas Island Cyril E King

mar. 3/18

1:55 pm-10:15 pm

1 stop8h 20m

$346

White PlainsProvidenciales

HPN - PLS

HPNPLS

White Plains Westchester County

lun. 3/24

6:35 pm-10:30 am

1 stop15h 55m

Providenciales

mié. 3/26

1:30 pm-11:06 pm

1 stop9h 36m

$346

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

lun. 4/28

6:00 am-4:00 pm

1 stop10h 00m

Nassau Intl

mié. 4/30

3:09 pm-10:18 pm

1 stop7h 09m

$351

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

sáb. 4/19

6:33 pm-9:10 am

1 stop15h 37m

Montego Bay Sangster Intl

mié. 4/23

12:55 pm-10:42 am

2 stops20h 47m

$355

White PlainsNassau

HPN - NAS

HPNNAS

White Plains Westchester County

lun. 3/17

6:35 pm-10:00 am

1 stop15h 25m

Nassau Intl

lun. 3/24

2:24 pm-9:52 pm

1 stop7h 28m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/3

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.

Travel insights for flights from Westchester County to Caribbean

Get recent, data-driven insights about flights from Westchester County to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $353). 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 marzo 3, 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.

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 marzo 3, 2025.
Alaska Airlines
8.0
Very good
9,710 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,710 reviews
Alaska Airlines
8.0
Very good
9,710 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,068 reviews
Alaska Airlines
8.0
Very good
9,710 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

LATAM Airlines
7.5
Good
1,763 reviews
Alaska Airlines
8.0
Very good
9,710 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

JetBlue
7.4
Good
3,008 reviews
Alaska Airlines
8.0
Very good
9,710 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,710 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $84. However, be on the lookout for offers from JetBlue 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 March is currently the most expensive (average of $353). 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 marzo 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$228FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$206Average$512FlexibilityNo cancel feeOn-time62%
DeltaCheapest$248Average$539FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$272Average$558FlexibilityNo cancel feeOn-time71%
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