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Jamaica

$174+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Apr 17 — Apr 241
Fri 4/17
Fri 4/24
1 adult, Economy
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Cheap 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 March 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/16. 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 3/2210:29 am
SWF
-
MBJ
1 stop25h 36m
Multiple Airlines
Sat 3/2812:00 pm
MBJ
-
SWF
1 stop20h 39m
Multiple Airlines
Deal found 3/16$512
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Sun 3/1512:29 pm
SWF
-
MBJ
1 stop23h 36m
Multiple Airlines
Wed 3/1812:00 pm
MBJ
-
SWF
1 stop20h 39m
Multiple Airlines
Deal found 3/14$662
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/231:00 pm
SWF
-
KIN
1 stop25h 28m
Multiple Airlines
Sat 8/298:06 pm
KIN
-
SWF
2 stops38h 00m
Multiple Airlines
Deal found 3/13$774
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 3/2210:29 am
SWF
-
KIN
1 stop26h 06m
Multiple Airlines
Sat 3/2812:32 pm
KIN
-
SWF
1 stop20h 07m
Multiple Airlines
Deal found 3/17$784
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:29 am
SWF
-
MBJ
1 stop25h 36m
Multiple Airlines
Sun 3/2912:00 pm
MBJ
-
SWF
2 stops19h 57m
Multiple Airlines
Deal found 3/13$822
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 4/510:29 am
SWF
-
KIN
1 stop26h 06m
Multiple Airlines
Sat 4/1112:32 pm
KIN
-
SWF
1 stop21h 23m
Multiple Airlines
Deal found 3/16$851
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 3/2210:29 am
SWF
-
MBJ
1 stop25h 36m
Multiple Airlines
Wed 3/251:55 pm
MBJ
-
SWF
2 stops42h 02m
Multiple Airlines
Deal found 3/16$909
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Thu 4/210:29 am
SWF
-
KIN
1 stop26h 06m
Multiple Airlines
Wed 4/812:32 pm
KIN
-
SWF
1 stop21h 23m
Multiple Airlines
Deal found 3/17$913
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 3/2610:29 am
SWF
-
KIN
1 stop26h 06m
Multiple Airlines
Sat 3/288:25 pm
KIN
-
SWF
2 stops35h 32m
Multiple Airlines
Deal found 3/15$968
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 7/297:46 pm
SWF
-
KIN
2 stops19h 08m
Multiple Airlines
Wed 8/52:37 pm
KIN
-
SWF
1 stop18h 01m
Multiple Airlines
Deal found 3/16$1,012
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/296:25 pm
SWF
-
MBJ
2 stops41h 40m
Multiple Airlines
Sat 4/1112:00 pm
MBJ
-
SWF
1 stop21h 55m
Multiple Airlines
Deal found 3/13$1,063

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 March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$512
(Kiwi.com)

One-way from

$174
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$474
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
From New Windsor Stewart to Jamaica
Search Deals
One-way flight from New Windsor Stewart to Jamaica
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 18, 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 round-trip

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Sun 8/23

1:00 pm-1:28 pm

1 stop25h 28m

Kingston Norman Manley

Sat 8/29

8:06 pm-11:06 am

2 stops38h 00m

$774

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Sun 4/5

10:29 am-11:35 am

1 stop26h 06m

Kingston Norman Manley

Sat 4/11

12:32 pm-10:55 am

1 stop21h 23m

$851

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Thu 4/2

10:29 am-11:35 am

1 stop26h 06m

Kingston Norman Manley

Wed 4/8

12:32 pm-10:55 am

1 stop21h 23m

$913
Quickest round-trip

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Wed 7/29

7:46 pm-1:54 pm

2 stops19h 08m

Kingston Norman Manley

Wed 8/5

2:37 pm-9:38 am

1 stop18h 01m

$1,012

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 3/29

6:25 pm-11:05 am

2 stops41h 40m

Montego Bay Sangster Intl

Sat 4/11

12:00 pm-10:55 am

1 stop21h 55m

$1,063
Cheapest one-way

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Sun 5/10

11:45 am-2:12 pm

1 stop27h 27m

$174

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 4/12

11:45 am-11:05 am

1 stop24h 20m

$178

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Sun 5/24

10:28 am-2:12 pm

1 stop28h 44m

$241

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Sun 4/12

11:45 am-11:35 am

1 stop24h 50m

$250

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Thu 4/23

11:45 am-2:12 pm

1 stop27h 27m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/14

Showing 1-10 of 21 resultsSorted by cheapest first
1
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3

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, March is the cheapest month in which you can book a flight from New Windsor to Jamaica (average of $187). Flying from New Windsor to Jamaica in July is currently the most expensive (average of $253). 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, March is the cheapest month in which you can book a flight from New Windsor to Jamaica (average of $187). Flying from New Windsor to Jamaica in July is currently the most expensive (average of $253). 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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See prices for flight routes from nearby airports that may be better suited for you.
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