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Stewart

$205+ Cheap flights from Jamaica to New Windsor (SWF)

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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — SWF
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Jamaica to Stewart

One-way flights from Jamaica to Stewart
Search for one-way flight options from Jamaica to Stewart. Find affordable one-way fares based on user searches. Data last updated December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:05 pmMBJ - SWF
1 stop22h 02mMultiple Airlines
Deal found 12/16$205
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/2512:57 pmMBJ - SWF
1 stop21h 22mMultiple Airlines
Deal found 12/16$214
This Mytrip deal was found by Cheapflights users on 12/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/261:00 pmMBJ - SWF
2 stops21h 13mMultiple Airlines
Deal found 12/15$243
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/412:57 pmMBJ - SWF
2 stops22h 11mMultiple Airlines
Deal found 12/16$244
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/251:17 pmKIN - SWF
1 stop21h 02mMultiple Airlines
Deal found 12/16$248
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1112:57 pmMBJ - SWF
1 stop21h 22mMultiple Airlines
Deal found 12/17$251
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:19 pmKIN - SWF
1 stop21h 48mMultiple Airlines
Deal found 12/16$265
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/912:57 pmMBJ - SWF
2 stops46h 36mMultiple Airlines
Deal found 12/17$268
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:05 pmMBJ - SWF
1 stop19h 58mMultiple Airlines
Deal found 12/17$272
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/223:05 pmMBJ - SWF
1 stop19h 58mMultiple Airlines
Deal found 12/16$284
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/812:57 pmMBJ - SWF
1 stop21h 22mMultiple Airlines
Deal found 12/16$290
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:19 pmKIN - SWF
1 stop21h 28mMultiple Airlines
Deal found 12/16$304

Find flight deals from Jamaica to Stewart

Keep the following information in mind while searching for Jamaica to Stewart flight deals. Data was last updated December 18, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Popular in

August

Cheapest in

February

Average price

$370
Provider with most accurate pricing for Montego Bay Sangster Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-New York (NYC) flights.
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Stewart 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 December 18, 2025.
Use the filters below to find and compare flights from Jamaica to New Windsor that are best for you.

Fly from

Jamaica

Fly to

Stewart

Route

Depart

Return

Price

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Thu 12/25

1:05 pm-11:07 am

1 stop22h 02m

$210

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 1/25

12:57 pm-10:19 am

1 stop21h 22m

$214

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Thu 2/26

1:00 pm-10:13 am

2 stops21h 13m

$243

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Wed 2/4

12:57 pm-11:08 am

2 stops22h 11m

$244

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 1/11

12:57 pm-10:19 am

1 stop21h 22m

$251

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Thu 12/25

1:19 pm-11:07 am

1 stop21h 48m

$265

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Fri 1/9

12:57 pm-9:58 am

2 stops45h 01m

$268

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Wed 12/24

3:05 pm-11:03 am

1 stop19h 58m

$272

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 1/18

12:57 pm-10:19 am

1 stop21h 22m

$284

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Sun 12/28

1:19 pm-10:47 am

1 stop21h 28m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 16 results
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Best time to book a flight from Jamaica to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Jamaica 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 Jamaica to New Windsor

What is the cheapest month to book a flight from Jamaica to New Windsor?

Currently, March is the cheapest month in which you can book a flight from Jamaica to New Windsor (average of $194). Flying from Jamaica to New Windsor in September is currently the most expensive (average of $335). 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.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Jamaica?

    New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly into when you book flights from Jamaica to New Windsor.

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

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

  • How can I find direct flights from Jamaica to Stewart?

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

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

    Yes. Cheapflights offers flight deals from Jamaica to Stewart 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 Jamaica to New Windsor?

    Currently, March is the cheapest month in which you can book a flight from Jamaica to New Windsor (average of $194). Flying from Jamaica to New Windsor in September is currently the most expensive (average of $335). 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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See prices for flight routes from nearby airports that may be better suited for you.
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