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Jamaica

$173+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MBJ
Aug 10 — Aug 171
Sun 8/10
Sun 8/17
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 August 5, 2025.

Round-trip from

$393
(Priceline)

One-way from

$173
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$586
From Westchester County to Jamaica
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One-way flight from Westchester County to Jamaica
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 5, 2025.

This Priceline deal was found by Cheapflights users on 8/5. 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.
Tue 9/99:39 amHPN - MBJ
1 stop5h 29mJetBlue
Fri 9/121:13 pmMBJ - HPN
1 stop8h 53mJetBlue
Deal found 8/5$393
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/45:29 pmHPN - MBJ
2 stops19h 36mAmerican Airlines
Thu 9/112:38 pmMBJ - HPN
2 stops17h 44mAmerican Airlines
Deal found 8/5$397
This JetBlue deal was found by Cheapflights users on 8/5. 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.
Thu 10/168:00 pmHPN - MBJ
1 stop13h 11mJetBlue
Tue 10/211:26 pmMBJ - HPN
1 stop8h 34mJetBlue
Deal found 8/5$402
This Priceline deal was found by Cheapflights users on 8/5. 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 9/48:55 pmHPN - MBJ
1 stop14h 45mJetBlue
Thu 9/1111:45 amMBJ - HPN
1 stop10h 03mJetBlue
Deal found 8/5$409
This JetBlue deal was found by Cheapflights users on 8/4. 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 10/198:00 pmHPN - MBJ
1 stop13h 11mJetBlue
Thu 10/2311:45 amMBJ - HPN
1 stop9h 45mJetBlue
Deal found 8/4$418
This American Airlines deal was found by Cheapflights users on 8/5. 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 10/176:59 pmHPN - MBJ
1 stop15h 14mAmerican Airlines
Tue 10/2111:50 amMBJ - HPN
1 stop7h 39mAmerican Airlines
Deal found 8/5$426
This Priceline deal was found by Cheapflights users on 8/5. 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.
Fri 9/268:55 pmHPN - MBJ
1 stop14h 35mJetBlue
Tue 9/3011:45 amMBJ - HPN
1 stop21h 21mJetBlue
Deal found 8/5$427
This American Airlines deal was found by Cheapflights users on 8/4. 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 9/196:50 pmHPN - KIN
2 stops18h 02mAmerican Airlines
Mon 9/221:00 pmKIN - HPN
2 stops20h 45mAmerican Airlines
Deal found 8/4$428
This American Airlines deal was found by Cheapflights users on 8/5. 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 10/96:59 pmHPN - MBJ
2 stops18h 01mAmerican Airlines
Mon 10/133:20 pmMBJ - HPN
2 stops20h 40mAmerican Airlines
Deal found 8/5$430
This JetBlue deal was found by Cheapflights users on 8/4. 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 8/259:00 pmHPN - MBJ
1 stop12h 15mJetBlue
Sat 8/301:10 pmMBJ - HPN
1 stop9h 21mJetBlue
Deal found 8/4$457
This Expedia deal was found by Cheapflights users on 8/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:00 pmHPN - KIN
1 stop21h 04mJetBlue
Tue 10/2112:15 pmKIN - HPN
1 stop9h 15mJetBlue
Deal found 8/5$459
This JetBlue deal was found by Cheapflights users on 8/5. 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 10/259:00 amHPN - MBJ
1 stop6h 08mJetBlue
Tue 10/283:14 pmMBJ - HPN
1 stop6h 48mJetBlue
Deal found 8/5$461

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 August 5, 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 9/9

9:39 am-2:08 pm

1 stop5h 29m

Montego Bay Sangster Intl

Fri 9/12

1:13 pm-11:06 pm

1 stop8h 53m

$393

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Thu 9/4

5:29 pm-12:05 pm

2 stops19h 36m

Montego Bay Sangster Intl

Thu 9/11

2:38 pm-9:22 am

2 stops17h 44m

$397

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Thu 10/16

8:00 pm-8:11 am

1 stop13h 11m

Montego Bay Sangster Intl

Tue 10/21

1:26 pm-11:00 pm

1 stop8h 34m

$402

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Thu 9/4

8:55 pm-10:40 am

1 stop14h 45m

Montego Bay Sangster Intl

Thu 9/11

11:45 am-10:48 pm

1 stop10h 03m

$409

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sun 10/19

8:00 pm-8:11 am

1 stop13h 11m

Montego Bay Sangster Intl

Thu 10/23

11:45 am-10:30 pm

1 stop9h 45m

$418

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Fri 10/17

6:59 pm-9:13 am

1 stop15h 14m

Montego Bay Sangster Intl

Tue 10/21

11:50 am-8:29 pm

1 stop7h 39m

$426

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Fri 9/26

8:55 pm-10:30 am

1 stop14h 35m

Montego Bay Sangster Intl

Tue 9/30

11:45 am-10:06 am

1 stop21h 21m

$427

White PlainsKingston

HPN - KIN

HPNKIN

White Plains Westchester County

Fri 9/19

6:50 pm-11:52 am

2 stops18h 02m

Kingston Norman Manley

Mon 9/22

1:00 pm-10:45 am

2 stops20h 45m

$428

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Thu 10/9

6:59 pm-12:00 pm

2 stops18h 01m

Montego Bay Sangster Intl

Mon 10/13

3:20 pm-1:00 pm

2 stops20h 40m

$430

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Mon 8/25

9:00 pm-8:15 am

1 stop12h 15m

Montego Bay Sangster Intl

Sat 8/30

1:10 pm-11:31 pm

1 stop9h 21m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

Showing 1-10 of 46 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 August 5, 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 August 5, 2025.
Peruse reviews from past customers who have flown with Delta, 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.
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

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
8.0
Very good
7,985 reviews
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

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
10,000 reviews
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

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
2,914 reviews
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

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.
WestJet
7.2
Good
2,997 reviews
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

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 Jamaica. 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 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 $173. JetBlue flights start at $199 while deals on Delta start at $214 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 $561). 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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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 August 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$351Average$480FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$425Average$680FlexibilityNo cancel feeOn-time62%

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