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Stewart

$201+ Cheap flights from Jamaica to New Windsor (SWF)

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — SWF
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Jamaica to Stewart

Cheapest flights from Jamaica to Stewart
Explore the most affordable flight options available from Jamaica to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/141:05 pmMBJ - SWF
1 stop22h 32mMultiple Airlines
Sun 12/216:28 pmSWF - MBJ
2 stops41h 37mMultiple Airlines
Deal found 10/30$571
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/141:19 pmKIN - SWF
1 stop22h 18mMultiple Airlines
Sun 12/216:28 pmSWF - KIN
2 stops41h 46mMultiple Airlines
Deal found 10/30$657

Cheap flight deals from Jamaica to Stewart

Keep the following information in mind while searching for Jamaica to Stewart flight deals. Data was last updated October 30, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$571
(Kiwi.com)

One-way from

$201
(Kiwi.com)

Popular in

August

Cheapest in

December

Average price

$389
Provider with most accurate pricing for Montego Bay Sangster Intl-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-New York (NYC) flights.
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From Jamaica to New Windsor Stewart
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One-way flight from Jamaica to New Windsor Stewart
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Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Jamaica to Stewart 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 October 30, 2025.
Use the filters below to find and compare flights from Jamaica to New Windsor that are best for you.

Fly from

Jamaica

Fly to

Stewart

Route

Depart

Return

Price

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 12/14

1:05 pm-11:37 am

1 stop22h 32m

New Windsor Stewart

Sun 12/21

6:28 pm-12:05 pm

2 stops41h 37m

$571

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Sun 12/14

1:19 pm-11:37 am

1 stop22h 18m

New Windsor Stewart

Sun 12/21

6:28 pm-12:14 pm

2 stops41h 46m

$657

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Thu 11/6

1:07 pm-10:41 am

1 stop21h 34m

$201

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 11/23

1:07 pm-10:07 am

1 stop21h 00m

$216

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sat 1/10

5:39 pm-10:19 am

2 stops40h 40m

$226

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 11/9

1:07 pm-11:11 am

1 stop22h 04m

$231

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 11/16

1:07 pm-11:11 am

1 stop22h 04m

$235

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Sun 12/14

1:19 pm-11:37 am

1 stop22h 18m

$237

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Thu 1/8

1:12 pm-10:19 am

1 stop21h 07m

$254

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sun 11/2

1:07 pm-11:11 am

1 stop22h 04m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 18 results
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Best time to book a flight from Jamaica to Stewart

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

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

Currently, August is the cheapest month in which you can book a flight from Jamaica to New Windsor (average of $168). Flying from Jamaica to New Windsor in September is currently the most expensive (average of $334). 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 Jamaica to Stewart. 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 into for flights to New Windsor from Jamaica?

    New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly into when you book flights from Jamaica to New Windsor.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Jamaica to New Windsor (average of $168). Flying from Jamaica to New Windsor in September is currently the most expensive (average of $334). 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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See prices for flight routes from nearby airports that may be better suited for you.
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