$227+ Cheap flights from New Windsor (SWF) to Jamaica
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Oct 20 — Oct 271
Round-trip
1 adult, Economy
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One-way
Cheapest flights from Stewart to JamaicaExplore 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 20, 2026.
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 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/66:49 pm -
2 stops18h 28m
Wed 1/131:45 pm -
1 stop20h 18m
Deal found 9/18![Multiple Airlines logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/106:49 pm -
2 stops18h 28m
Wed 1/131:45 pm -
1 stop20h 18m
Deal found 9/18![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 12/136:49 pm -
2 stops18h 28m
Wed 1/131:45 pm -
1 stop20h 18m
Deal found 9/19![Multiple Airlines logo]()
$515
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 12/136:49 pm -
2 stops18h 28m
Sat 1/161:45 pm -
1 stop20h 18m
Deal found 9/19![Multiple Airlines logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 12/187:15 pm -
2 stops44h 00m
Wed 1/131:45 pm -
1 stop20h 18m
Deal found 9/19![Multiple Airlines logo]()
$832
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/2312:39 pm -
2 stops24h 29m
Sat 1/91:45 pm -
1 stop20h 18m
Deal found 9/17![Multiple Airlines logo]()
$940
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Tue 12/226:54 pm -
1 stop17h 51m
Tue 12/292:25 pm -
2 stops21h 14m
Deal found 9/19![Multiple Airlines logo]()
$996
Best flights from Stewart to JamaicaDiscover carefully curated flight deals from Stewart to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
Discover carefully curated flight deals from Stewart to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/66:49 pm -
2 stops18h 28m
Wed 1/131:45 pm -
1 stop20h 18m
Deal found 9/18![Multiple Airlines logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/106:49 pm -
2 stops18h 28m
Wed 1/131:45 pm -
1 stop20h 18m
Deal found 9/18![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 12/136:49 pm -
2 stops18h 28m
Wed 1/131:45 pm -
1 stop20h 18m
Deal found 9/19![Multiple Airlines logo]()
$515
One-way flights from Stewart to JamaicaSearch for one-way flight options from Stewart to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
Search for one-way flight options from Stewart to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 12/66:49 pm -
2 stops18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/1012:39 pm -
3 stops26h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 12/106:49 pm -
2 stops18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 11/712:39 pm -
3 stops26h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$239
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.
Sun 12/136:49 pm -
2 stops18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 11/1412:39 pm -
3 stops26h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 12/512:39 pm -
3 stops24h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/2511:58 am -
3 stops50h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 12/136:49 pm -
3 stops43h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/1712:39 pm -
3 stops31h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/3112:39 pm -
3 stops51h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/111:58 am -
3 stops49h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$398
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 September 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $495 (Kiwi.com) |
One-way from | $227 (Kiwi.com) |
Popular in | December |
Cheapest in | November |
Average price | $474 |
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 7,457,451 searches. Data last updated September 20, 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
Cheapest round-trip
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Thu 11/5
11:00 am-3:08 pm
2 stops28h 08m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Quickest round-trip
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Thu 12/3
6:49 pm-1:13 pm
2 stops18h 24m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$311
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Thu 10/15
10:56 am-2:33 pm
2 stops28h 37m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$320
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Sun 9/27
10:56 am-2:27 pm
2 stops28h 31m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$338
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Sat 11/21
12:39 pm-12:56 pm
3 stops24h 17m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$338
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Sat 10/17
12:39 pm-2:33 pm
3 stops26h 54m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$351
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Fri 12/11
12:16 pm-1:17 pm
3 stops25h 01m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$363
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Wed 11/4
12:39 pm-3:29 pm
2 stops26h 50m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$376
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Sun 12/13
6:49 pm-1:17 pm
2 stops18h 28m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$378
New WindsorKingston
SWF New Windsor Stewart - KIN Kingston Norman Manley
SWFKIN
New Windsor Stewart
Wed 10/28
12:39 pm-2:30 pm
3 stops50h 51m
Kingston Norman Manley
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$403
Showing 1-10 of 19 resultsSorted by cheapest first
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.
SWF-MBJ
SWF-KIN
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
SWF-JM0
SWF-MBJ
SWF-KIN
No data available for this route at this time. Please check back soon.
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