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$152+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 6/1410:28 am
SWF
-
MBJ
1 stop25h 34m
Multiple Airlines
Sun 6/217:30 pm
MBJ
-
SWF
2 stops38h 38m
Multiple Airlines
Deal found 1/27$746
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 6/1410:28 am
SWF
-
MBJ
1 stop25h 34m
Multiple Airlines
Wed 6/2412:00 pm
MBJ
-
SWF
1 stop20h 38m
Multiple Airlines
Deal found 1/27$755
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 6/125:55 pm
SWF
-
KIN
2 stops42h 10m
Multiple Airlines
Sat 6/2012:00 pm
KIN
-
SWF
1 stop20h 38m
Multiple Airlines
Deal found 1/28$1,169

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$746
(Kiwi.com)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$439
Provider with most accurate pricing for New York (NYC)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Montego Bay Sangster Intl flights.
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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. 0% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 29, 2026.
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

Sun 6/14

10:28 am-11:02 am

1 stop25h 34m

Montego Bay Sangster Intl

Sun 6/21

7:30 pm-11:08 am

2 stops38h 38m

$746

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 6/14

10:28 am-11:02 am

1 stop25h 34m

Montego Bay Sangster Intl

Wed 6/24

12:00 pm-9:38 am

1 stop20h 38m

$755

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Fri 6/12

5:55 pm-11:05 am

2 stops42h 10m

Kingston Norman Manley

Sat 6/20

12:00 pm-9:38 am

1 stop20h 38m

$1,169

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 2/9

11:09 am-12:02 pm

1 stop24h 53m

$152

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Thu 3/5

10:09 am-12:15 pm

1 stop26h 06m

$164

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 2/23

12:11 pm-12:02 pm

3 stops23h 51m

$179

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 4/5

10:29 am-10:58 am

1 stop25h 29m

$216

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 2/6

11:09 am-12:02 pm

1 stop24h 53m

$234

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 5/17

11:45 am-11:02 am

1 stop24h 17m

$242

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Thu 4/2

10:29 am-11:00 am

1 stop25h 31m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 16 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, March is the cheapest month in which you can book a flight from New Windsor to Jamaica (average of $164). 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 $164). 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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