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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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MBJ
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
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 January 15, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$365
(American Airlines)

One-way from

$173
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$435
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. 0% potential increase in price ($0 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This American Airlines deal was found by Cheapflights users on 1/14. 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 2/285:29 pm
HPN
-
MBJ
2 stops20h 04m
American Airlines
Sat 3/72:33 pm
MBJ
-
HPN
2 stops17h 56m
American Airlines
Deal found 1/14$365
This Delta deal was found by Cheapflights users on 1/13. 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.
Fri 5/156:00 am
HPN
-
MBJ
1 stop10h 29m
Delta
Thu 5/284:55 pm
MBJ
-
HPN
1 stop15h 57m
Delta
Deal found 1/13$372
This American Airlines deal was found by Cheapflights users on 1/14. 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 1/306:40 pm
HPN
-
MBJ
1 stop16h 38m
American Airlines
Wed 2/42:34 pm
MBJ
-
HPN
1 stop7h 21m
American Airlines
Deal found 1/14$376
This Delta deal was found by Cheapflights users on 1/13. 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 5/186:00 am
HPN
-
MBJ
1 stop10h 29m
Delta
Fri 5/224:55 pm
MBJ
-
HPN
2 stops17h 49m
Delta
Deal found 1/13$377
This Delta deal was found by Cheapflights users on 1/14. 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.
Fri 2/63:10 pm
HPN
-
MBJ
2 stops20h 03m
Delta
Thu 2/124:05 pm
MBJ
-
HPN
2 stops23h 44m
Delta
Deal found 1/14$379
This American Airlines deal was found by Cheapflights users on 1/14. 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 4/76:57 pm
HPN
-
MBJ
1 stop15h 16m
American Airlines
Sat 4/114:44 pm
MBJ
-
HPN
2 stops16h 46m
American Airlines
Deal found 1/14$387
This American Airlines deal was found by Cheapflights users on 1/15. 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 5/16:00 am
HPN
-
MBJ
1 stop10h 44m
American Airlines
Sun 5/312:51 pm
MBJ
-
HPN
2 stops19h 38m
American Airlines
Deal found 1/15$392
This American Airlines deal was found by Cheapflights users on 1/13. 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.
Mon 2/166:54 pm
HPN
-
MBJ
2 stops18h 39m
American Airlines
Sat 2/212:33 pm
MBJ
-
HPN
2 stops18h 56m
American Airlines
Deal found 1/13$401
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Sun 2/227:00 am
HPN
-
MBJ
1 stop6h 33m
American Airlines
Sat 2/2811:07 am
MBJ
-
HPN
1 stop12h 20m
American Airlines
Deal found 1/14$424
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Sun 3/16:54 pm
HPN
-
KIN
2 stops19h 35m
American Airlines
Sun 3/82:34 pm
KIN
-
HPN
2 stops21h 33m
American Airlines
Deal found 1/14$444
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Sun 4/195:16 pm
HPN
-
KIN
2 stops21h 06m
American Airlines
Thu 4/237:00 am
KIN
-
HPN
2 stops25h 29m
American Airlines
Deal found 1/14$447
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Mon 2/27:00 am
HPN
-
KIN
1 stop7h 26m
American Airlines
Fri 2/67:00 am
KIN
-
HPN
1 stop15h 59m
American Airlines
Deal found 1/14$449

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 January 15, 2026.
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

Mon 5/18

6:00 am-1:16 pm

1 stop8h 16m

Montego Bay Sangster Intl

Thu 5/28

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Fri 5/15

6:00 am-3:29 pm

1 stop10h 29m

Montego Bay Sangster Intl

Wed 5/27

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sat 5/16

6:00 am-3:29 pm

1 stop10h 29m

Montego Bay Sangster Intl

Thu 5/28

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Mon 5/18

6:00 am-1:16 pm

1 stop8h 16m

Montego Bay Sangster Intl

Wed 5/27

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Tue 5/19

6:00 am-3:29 pm

1 stop10h 29m

Montego Bay Sangster Intl

Thu 5/28

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sat 5/16

6:00 am-3:29 pm

1 stop10h 29m

Montego Bay Sangster Intl

Wed 5/27

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Wed 5/20

6:00 am-3:29 pm

1 stop10h 29m

Montego Bay Sangster Intl

Wed 5/27

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Sun 5/17

6:00 am-3:29 pm

1 stop10h 29m

Montego Bay Sangster Intl

Thu 5/28

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Fri 5/15

6:00 am-3:29 pm

1 stop10h 29m

Montego Bay Sangster Intl

Thu 5/28

4:55 pm-9:52 am

1 stop15h 57m

$372

White PlainsMontego Bay

HPN - MBJ

HPNMBJ

White Plains Westchester County

Fri 1/30

6:40 pm-11:18 am

1 stop16h 38m

Montego Bay Sangster Intl

Wed 2/4

2:34 pm-9:55 pm

1 stop7h 21m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 26 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.

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 January 15, 2026.
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
11,132 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,132 reviews
American Airlines
7.2
Good
11,132 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
JetBlue
7.2
Good
2,887 reviews
American Airlines
7.2
Good
11,132 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 8h 16m. Your travel time can differ by up to 11h 19m. Airlines will cover a distance of 1578 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$387Average$740FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$394Average$583FlexibilityNo cancel feeOn-time71%

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