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Jamaica

$215+ Cheap flights from Westchester County to Jamaica

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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MBJ
Oct 31 — Nov 71
Fri 10/31
Fri 11/7
1 adult, Economy
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Cheap flight deals from Westchester County to Jamaica

Keep the following information in mind while searching for Westchester County to Jamaica flight deals. Data was last updated October 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$353
(JetBlue)

One-way from

$215
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$459
Provider with most accurate pricing for New York (NYC)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Montego Bay Sangster Intl flights.
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From Westchester County to Jamaica
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One-way flight from Westchester County to Jamaica
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Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Westchester County to Jamaica

Cheapest flights from Westchester County to Jamaica
Explore the most affordable flight options available from Westchester County to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 2025.

This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:00 amHPN - MBJ
1 stop8h 10mJetBlue
Tue 11/44:30 pmMBJ - HPN
1 stop6h 52mJetBlue
Deal found 9/29$353
This JetBlue deal was found by Cheapflights users on 9/30. 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.
Sun 10/267:00 amHPN - MBJ
1 stop5h 40mJetBlue
Wed 10/2912:45 pmMBJ - HPN
1 stop9h 37mJetBlue
Deal found 9/30$362
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Tue 10/287:45 amHPN - MBJ
1 stop6h 20mAmerican Airlines
Tue 11/43:50 pmMBJ - HPN
1 stop6h 40mAmerican Airlines
Deal found 10/1$371
This Priceline deal was found by Cheapflights users on 9/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:55 pmHPN - KIN
1 stop17h 11mJetBlue
Wed 10/292:16 pmKIN - HPN
1 stop8h 06mJetBlue
Deal found 9/30$371
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 11/116:43 pmHPN - MBJ
2 stops19h 29mAmerican Airlines
Sat 11/155:22 pmMBJ - HPN
1 stop16h 07mAmerican Airlines
Deal found 9/29$375
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 12/115:59 pmHPN - MBJ
1 stop21h 23mAmerican Airlines
Wed 12/174:51 pmMBJ - HPN
1 stop16h 38mAmerican Airlines
Deal found 10/1$378
This Priceline deal was found by Cheapflights users on 9/28. 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.
Thu 11/137:00 amHPN - KIN
1 stop11h 12mJetBlue
Mon 11/177:22 pmKIN - HPN
1 stop28h 05mJetBlue
Deal found 9/28$380
This JetBlue deal was found by Cheapflights users on 10/1. 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.
Wed 10/298:30 amHPN - MBJ
1 stop6h 14mJetBlue
Mon 11/34:30 pmMBJ - HPN
1 stop6h 57mJetBlue
Deal found 10/1$387
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 10/173:21 pmHPN - MBJ
2 stops18h 52mAmerican Airlines
Fri 10/242:30 pmMBJ - HPN
2 stops7h 59mAmerican Airlines
Deal found 10/1$388
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/259:39 amHPN - MBJ
1 stop5h 29mJetBlue
Wed 10/2912:45 pmMBJ - HPN
1 stop9h 37mJetBlue
Deal found 9/29$396
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/38:30 amHPN - MBJ
1 stop6h 16mJetBlue
Fri 11/74:30 pmMBJ - HPN
1 stop6h 57mJetBlue
Deal found 9/29$406
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sat 10/256:59 pmHPN - KIN
2 stops16h 48mAmerican Airlines
Wed 10/297:00 amKIN - HPN
2 stops13h 59mAmerican Airlines
Deal found 9/30$410

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Jamaica 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 October 1, 2025.
Use the filters below to find and compare flights from Westchester County to Jamaica that are best for you.

Fly from

Westchester County

Fly to

Jamaica

Route

Depart

Return

Price

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Tue 11/11

7:00 am-3:10 pm

1 stop8h 10m

Montego Bay Sangster Intl

Sat 11/15

4:30 pm-11:27 pm

1 stop6h 57m

$353

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Mon 11/10

7:00 am-12:45 pm

1 stop5h 45m

Montego Bay Sangster Intl

Fri 11/14

1:50 pm-9:37 pm

1 stop7h 47m

$353

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Tue 10/28

7:00 am-2:10 pm

1 stop8h 10m

Montego Bay Sangster Intl

Tue 11/4

4:30 pm-11:22 pm

1 stop6h 52m

$353

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sun 10/26

7:00 am-11:40 am

1 stop5h 40m

Montego Bay Sangster Intl

Wed 10/29

12:45 pm-11:22 pm

1 stop9h 37m

$362

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Tue 11/11

7:11 am-3:28 pm

1 stop8h 17m

Montego Bay Sangster Intl

Sat 11/15

5:22 pm-9:29 am

1 stop16h 07m

$371

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sun 1/25

6:00 am-3:20 pm

1 stop9h 20m

Montego Bay Sangster Intl

Sat 1/31

4:30 pm-9:29 am

2 stops16h 59m

$375

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Tue 10/28

6:00 am-3:05 pm

2 stops10h 05m

Montego Bay Sangster Intl

Tue 11/4

4:28 pm-10:57 am

2 stops18h 29m

$376

White PlainsKingston

HPN - KIN

HPNKIN

White Plains Westchester County

Thu 11/13

7:00 am-6:12 pm

1 stop11h 12m

Kingston Norman Manley

Mon 11/17

7:22 pm-11:27 pm

1 stop28h 05m

$380

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sun 1/25

8:15 am-2:48 pm

1 stop6h 33m

Montego Bay Sangster Intl

Sat 1/31

2:00 pm-10:30 pm

1 stop8h 30m

$387

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Wed 10/29

8:30 am-1:44 pm

1 stop6h 14m

Montego Bay Sangster Intl

Mon 11/3

4:30 pm-11:27 pm

1 stop6h 57m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Showing 1-10 of 34 results
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Best time to book a flight from Westchester County to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica 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 Jamaica

What is the cheapest time of day to fly from REU to JM?

Find hourly flight availability from Westchester County to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 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 Jamaica as you normally would.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated October 1, 2025.
Peruse reviews from past customers who have flown with American Airlines from Westchester County to Jamaica to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,030 reviews

Comfort

7.2

Boarding

7.5

Crew

8.0

Food

6.4

Overall

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
11,030 reviews
American Airlines
7.2
Good
11,030 reviews

Comfort

7.2

Boarding

7.5

Crew

8.0

Food

6.4

Overall

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 Jamaica. 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 Jamaica?

    JetBlue, American Airlines, and Delta can get you from Westchester County to Jamaica in just under 8h 10m. Your travel time can differ by up to 5h 50m. Airlines will cover a distance of 1578 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $231. JetBlue flights start at $279 while deals on Delta start at $362 one-way.

  • Can I find deals for flights from Westchester County to Jamaica that include hotel bookings?

    Yes. In addition to deals on Westchester County to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Jamaica.

  • Can I find deals for business class flights from Westchester County to Jamaica?

    Yes. Cheapflights offers flight deals from Westchester County to Jamaica 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 Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Westchester County to Jamaica (average of $403). Flying from Westchester County to Jamaica in July is currently the most expensive (average of $560). 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 Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Westchester County to Jamaica

Discover the top airline that operate flights from Westchester County to Jamaica. 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 October 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$351Average$480FlexibilityNo cancel feeOn-time71%

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