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$154+ Cheap flights from New Windsor (SWF) 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Stewart to Jamaica

Keep the following information in mind while searching for Stewart to Jamaica flight deals. Data was last updated September 16, 2025.

Round-trip from

$373
(Kiwi.com)

One-way from

$154
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$436
From New Windsor Stewart to Jamaica
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One-way flight from New Windsor Stewart 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. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Stewart to Jamaica

Cheapest flights from Stewart to Jamaica
Explore the most affordable flight options available from Stewart to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:11 pmSWF - MBJ
2 stops23h 06mMultiple Airlines
Sun 10/512:09 pmMBJ - SWF
1 stop21h 02mMultiple Airlines
Deal found 9/15$373
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:31 amSWF - MBJ
1 stop24h 29mMultiple Airlines
Thu 10/2312:09 pmMBJ - SWF
1 stop21h 32mMultiple Airlines
Deal found 9/14$374
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2811:43 amSWF - MBJ
2 stops24h 22mMultiple Airlines
Sun 10/512:09 pmMBJ - SWF
1 stop21h 02mMultiple Airlines
Deal found 9/15$399
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:17 pmSWF - KIN
1 stop23h 56mMultiple Airlines
Thu 12/41:28 pmKIN - SWF
1 stop22h 09mMultiple Airlines
Deal found 9/14$442
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1011:41 amSWF - MBJ
1 stop26h 39mMultiple Airlines
Sun 10/122:50 pmMBJ - SWF
1 stop18h 21mMultiple Airlines
Deal found 9/14$515
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:43 amSWF - MBJ
2 stops27h 32mMultiple Airlines
Sun 11/231:12 pmMBJ - SWF
1 stop20h 55mMultiple Airlines
Deal found 9/15$533
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:01 pmSWF - MBJ
1 stop24h 04mMultiple Airlines
Sat 11/225:39 pmMBJ - SWF
2 stops40h 28mMultiple Airlines
Deal found 9/15$536
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 12/512:27 pmSWF - KIN
1 stop23h 46mMultiple Airlines
Sun 12/281:28 pmKIN - SWF
1 stop21h 19mMultiple Airlines
Deal found 9/16$576
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/1512:27 pmSWF - KIN
1 stop8h 08mMultiple Airlines
Fri 12/197:05 amKIN - SWF
1 stop11h 01mMultiple Airlines
Deal found 9/16$805
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:34 pmSWF - MBJ
1 stop20h 03mMultiple Airlines
Mon 12/294:53 pmMBJ - SWF
2 stops47h 51mMultiple Airlines
Deal found 9/14$806
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:17 pmSWF - MBJ
1 stop23h 48mMultiple Airlines
Sat 11/291:12 pmMBJ - SWF
1 stop20h 10mMultiple Airlines
Deal found 9/14$808
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/245:34 pmSWF - KIN
2 stops20h 28mMultiple Airlines
Sun 12/281:28 pmKIN - SWF
1 stop21h 19mMultiple Airlines
Deal found 9/16$824

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart 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 September 16, 2025.
Use the filters below to find and compare flights from New Windsor to Jamaica that are best for you.

Fly from

Stewart

Fly to

Jamaica

Route

Depart

Return

Price

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/3

12:11 pm-10:17 am

2 stops23h 06m

Montego Bay Sangster Intl

Sun 10/5

12:09 pm-10:11 am

1 stop21h 02m

$373

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/17

11:31 am-11:00 am

1 stop24h 29m

Montego Bay Sangster Intl

Thu 10/23

12:09 pm-10:41 am

1 stop21h 32m

$373

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 9/28

11:43 am-11:05 am

2 stops24h 22m

Montego Bay Sangster Intl

Sun 10/5

12:09 pm-10:11 am

1 stop21h 02m

$399

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Wed 11/26

12:17 pm-12:13 pm

1 stop23h 56m

Kingston Norman Manley

Thu 12/4

1:28 pm-11:37 am

1 stop22h 09m

$442

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/10

11:41 am-1:20 pm

1 stop26h 39m

Montego Bay Sangster Intl

Sun 10/12

2:50 pm-10:11 am

1 stop18h 21m

$515

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 11/20

11:43 am-3:15 pm

2 stops27h 32m

Montego Bay Sangster Intl

Sun 11/23

1:12 pm-10:07 am

1 stop20h 55m

$533

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/8

12:27 pm-12:05 pm

1 stop23h 38m

Montego Bay Sangster Intl

Sun 12/21

3:05 pm-7:35 pm

1 stop28h 30m

$533

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 11/17

12:01 pm-12:05 pm

1 stop24h 04m

Montego Bay Sangster Intl

Sat 11/22

5:39 pm-10:07 am

2 stops40h 28m

$536

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Wed 11/26

12:17 pm-12:05 pm

1 stop23h 48m

Montego Bay Sangster Intl

Sat 11/29

1:12 pm-9:22 am

1 stop20h 10m

$808

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/15

12:27 pm-12:05 pm

1 stop23h 38m

Montego Bay Sangster Intl

Sat 1/3

5:39 pm-10:47 am

2 stops41h 08m

$1,070

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 26 results
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Best time to book a flight from Stewart to Jamaica

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

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Jamaica (average of $403). Flying from New Windsor 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.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Jamaica. 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 from for flights from New Windsor to Jamaica?

    For a flight from New Windsor to Jamaica, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Jamaica (average of $403). Flying from New Windsor 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

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