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Stewart

$203+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — SWF
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
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Cheap 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 February 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/1. 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 7/1812:00 pm
MBJ
-
SWF
1 stop20h 38m
Multiple Airlines
Sun 8/210:28 am
SWF
-
MBJ
1 stop25h 34m
Multiple Airlines
Deal found 2/1$724

Find flight deals from Jamaica to Stewart

Keep the following information in mind while searching for Jamaica to Stewart flight deals. Data was last updated February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

August

Cheapest in

February

Average price

$324
Provider with most accurate pricing for Montego Bay Sangster Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-New York (NYC) flights.
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 2, 2026.
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

Sat 7/18

12:00 pm-9:38 am

1 stop20h 38m

New Windsor Stewart

Sun 8/2

10:28 am-11:02 am

1 stop25h 34m

$724

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sat 2/14

1:00 pm-10:52 am

1 stop21h 52m

$211

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Wed 4/8

12:00 pm-10:55 am

1 stop21h 55m

$212

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-11:02 am

1 stop22h 02m

$242

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Sat 3/7

1:00 pm-8:19 am

1 stop19h 19m

$258

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Wed 4/8

12:32 pm-10:55 am

1 stop21h 23m

$269

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Thu 2/26

1:00 pm-11:31 am

3 stops22h 31m

$271

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Wed 2/11

12:57 pm-11:08 am

2 stops22h 11m

$303

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Wed 4/15

12:00 pm-10:55 am

1 stop21h 55m

$314

Montego BayNew Windsor

MBJ - SWF

MBJSWF

Montego Bay Sangster Intl

Fri 2/27

1:00 pm-11:08 am

2 stops46h 08m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 20 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, March is the cheapest month in which you can book a flight from Jamaica to New Windsor (average of $194). Flying from Jamaica to New Windsor in September is currently the most expensive (average of $335). 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, March is the cheapest month in which you can book a flight from Jamaica to New Windsor (average of $194). Flying from Jamaica to New Windsor in September is currently the most expensive (average of $335). 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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