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Jamaica

$163+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MBJ
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$351
(Delta)

One-way from

$163
(Delta)

Popular in

December

Cheapest in

March

Average price

$457
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. 1% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/24. 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 12/176:43 pmHPN - MBJ
2 stops15h 20mAmerican Airlines
Sat 12/204:11 pmMBJ - HPN
2 stops18h 23mAmerican Airlines
Deal found 11/24$355
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/2511:04 amHPN - MBJ
2 stops23h 17mAmerican Airlines
Thu 1/224:16 pmMBJ - HPN
2 stops17h 13mAmerican Airlines
Deal found 11/24$356
This American Airlines deal was found by Cheapflights users on 11/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:04 amHPN - MBJ
2 stops23h 17mAmerican Airlines
Fri 1/91:58 pmMBJ - HPN
2 stops20h 32mAmerican Airlines
Deal found 11/26$367
This JetBlue deal was found by Cheapflights users on 11/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/109:15 amHPN - MBJ
1 stop6h 20mJetBlue
Tue 3/241:08 pmMBJ - HPN
1 stop8h 50mJetBlue
Deal found 11/26$379
This Delta deal was found by Cheapflights users on 11/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:10 amHPN - MBJ
1 stop8h 03mDelta
Tue 3/2411:35 amMBJ - HPN
1 stop9h 32mDelta
Deal found 11/26$385
This Delta deal was found by Cheapflights users on 11/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:17 pmHPN - MBJ
2 stops20h 56mDelta
Tue 3/2411:35 amMBJ - HPN
1 stop9h 32mDelta
Deal found 11/26$390
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Thu 12/2511:04 amHPN - MBJ
2 stops23h 17mAmerican Airlines
Mon 12/294:24 pmMBJ - HPN
2 stops17h 05mAmerican Airlines
Deal found 11/25$392
This JetBlue deal was found by Cheapflights users on 11/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/99:15 amHPN - MBJ
1 stop6h 20mJetBlue
Tue 3/242:43 pmMBJ - HPN
1 stop7h 15mJetBlue
Deal found 11/26$397
This Delta deal was found by Cheapflights users on 11/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/306:00 amHPN - MBJ
1 stop6h 52mDelta
Wed 2/114:45 pmMBJ - HPN
1 stop16h 58mDelta
Deal found 11/26$403
This Delta deal was found by Cheapflights users on 11/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:14 pmHPN - MBJ
2 stops20h 59mDelta
Thu 2/124:44 pmMBJ - HPN
2 stops23h 48mDelta
Deal found 11/26$408
This JetBlue deal was found by Cheapflights users on 11/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/109:15 amHPN - MBJ
1 stop6h 20mJetBlue
Thu 3/262:43 pmMBJ - HPN
1 stop7h 15mJetBlue
Deal found 11/26$419
This American Airlines deal was found by Cheapflights users on 11/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:43 pmHPN - KIN
2 stops17h 59mAmerican Airlines
Thu 2/1211:09 amKIN - HPN
2 stops22h 20mAmerican Airlines
Deal found 11/26$521

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 November 26, 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 2/24

6:00 am-12:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Sat 2/28

2:19 pm-10:00 pm

1 stop7h 41m

$351

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Wed 12/17

6:43 pm-10:03 am

2 stops15h 20m

Montego Bay Sangster Intl

Sat 12/20

4:11 pm-10:34 am

2 stops18h 23m

$355

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Mon 1/19

6:40 pm-11:13 am

1 stop16h 33m

Montego Bay Sangster Intl

Fri 1/23

4:05 pm-12:06 pm

2 stops20h 01m

$356

White PlainsKingston

HPN - KIN

HPNKIN

White Plains Westchester County

Tue 1/20

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Thu 1/22

9:00 am-10:00 pm

1 stop13h 00m

$415

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Wed 12/10

9:15 am-3:35 pm

1 stop6h 20m

Montego Bay Sangster Intl

Thu 3/26

2:43 pm-10:58 pm

1 stop7h 15m

$419

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Mon 12/15

9:00 am-3:35 pm

1 stop6h 35m

Montego Bay Sangster Intl

Thu 3/26

1:08 pm-10:58 pm

1 stop8h 50m

$419

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Mon 12/15

9:00 am-3:35 pm

1 stop6h 35m

Montego Bay Sangster Intl

Fri 12/26

9:25 am-10:00 pm

1 stop12h 35m

$420

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Fri 12/12

9:10 am-3:35 pm

1 stop6h 25m

Montego Bay Sangster Intl

Fri 5/29

12:50 pm-10:47 pm

1 stop8h 57m

$434

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Fri 12/12

9:10 am-3:35 pm

1 stop6h 25m

Montego Bay Sangster Intl

Thu 5/28

12:50 pm-10:47 pm

1 stop8h 57m

$434

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Thu 12/11

6:10 am-2:13 pm

1 stop8h 03m

Montego Bay Sangster Intl

Thu 3/26

2:25 pm-3:49 pm

2 stops24h 24m

$442

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 33 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 month to book a flight from Westchester County to Jamaica?

Currently, April is the cheapest month in which you can book a flight from Westchester County to Jamaica (average of $386). Flying from Westchester County to Jamaica in December is currently the most expensive (average of $591). 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 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 November 26, 2025.

One of the essential ways to save on airfare from Westchester County to Jamaica is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 35% on airfare.

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 November 26, 2025.
Peruse reviews from past customers who have flown with American Airlines and JetBlue 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
11,038 reviews

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

8.0

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.
American Airlines
7.2
Good
11,038 reviews
American Airlines
7.2
Good
11,038 reviews

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

8.0

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.
JetBlue
7.2
Good
2,905 reviews
American Airlines
7.2
Good
11,038 reviews

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

8.0

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.

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?

    Delta and American Airlines can get you from Westchester County to Jamaica in just under 6h 54m. Your travel time can differ by up to 8h 26m. 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 Delta, which is currently one of the cheapest options available, starting at $163. JetBlue flights start at $173 while deals on American Airlines start at $193 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, April is the cheapest month in which you can book a flight from Westchester County to Jamaica (average of $386). Flying from Westchester County to Jamaica in December is currently the most expensive (average of $591). 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 2 airlines flying from Westchester County to Jamaica

Discover the top 2 airlines 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$373Average$488FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$387Average$564FlexibilityNo cancel feeOn-time62%

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