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$220+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
1 adult, Economy
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Cheap flight deals from Stewart to Jamaica

One-way flights from Stewart to Jamaica
Search for one-way flight options from Stewart to Jamaica. Find affordable one-way fares based on user searches. Data last updated May 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:41 am
SWF
-
MBJ
2 stops51h 30m
Multiple Airlines
Deal found 5/4$220
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 8/231:00 pm
SWF
-
MBJ
2 stops24h 21m
Multiple Airlines
Deal found 5/7$252
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Sat 8/2912:05 pm
SWF
-
MBJ
2 stops25h 16m
Multiple Airlines
Deal found 5/7$257
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:05 pm
SWF
-
MBJ
2 stops25h 22m
Multiple Airlines
Deal found 5/4$260
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Sat 8/2212:05 pm
SWF
-
MBJ
2 stops25h 16m
Multiple Airlines
Deal found 5/7$263
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:28 am
SWF
-
MBJ
2 stops26h 59m
Multiple Airlines
Deal found 5/5$273
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:05 pm
SWF
-
MBJ
2 stops25h 06m
Multiple Airlines
Deal found 5/5$276
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/712:16 pm
SWF
-
KIN
2 stops45h 11m
Multiple Airlines
Deal found 5/4$354
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:05 pm
SWF
-
KIN
3 stops54h 05m
Multiple Airlines
Deal found 5/4$359
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Sat 5/3012:05 pm
SWF
-
KIN
3 stops45h 05m
Multiple Airlines
Deal found 5/8$362
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/1712:05 pm
SWF
-
KIN
3 stops54h 05m
Multiple Airlines
Deal found 5/8$370
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 8/2612:05 pm
SWF
-
KIN
3 stops45h 05m
Multiple Airlines
Deal found 5/6$376

Find flight deals from Stewart to Jamaica

Keep the following information in mind while searching for Stewart to Jamaica flight deals. Data was last updated May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

September

Average price

$496
Provider with most accurate pricing for New York (NYC)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Montego Bay Sangster Intl flights.
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 9, 2026.
Use the filters below to find and compare flights from New Windsor to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest one-way

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sat 8/1

12:05 pm-12:27 pm

2 stops25h 22m

$260

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sat 6/6

12:05 pm-12:11 pm

3 stops25h 06m

$279

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 6/1

9:41 am-12:11 pm

2 stops51h 30m

$281

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 7/12

10:28 am-12:27 pm

2 stops26h 59m

$290
Quickest one-way

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 8/20

1:00 pm-12:21 pm

2 stops24h 21m

$294

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Wed 7/29

7:46 pm-12:27 pm

2 stops41h 41m

$315

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 8/13

10:28 am-9:12 am

3 stops47h 44m

$323

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 8/28

10:56 am-12:21 pm

2 stops50h 25m

$341

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 7/23

10:28 am-12:27 pm

2 stops26h 59m

$349

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 6/21

10:28 am-12:21 pm

2 stops26h 53m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 22 resultsSorted by cheapest first
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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
No data available for this route at this time. Please check back soon.

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.

See more FAQs

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