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Montego Bay

$171+ Cheap flights from New Windsor (SWF) to Montego Bay (MBJ)

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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Find flight deals from Stewart to Montego Bay

Cheapest flights from Stewart to Montego Bay
Explore the most affordable flight options available from Stewart to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/1411:01 amSWF - MBJ
1 stop25h 01mMultiple Airlines
Sun 11/161:07 pmMBJ - SWF
1 stop22h 04mMultiple Airlines
Deal found 11/5$439
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 11/2410:57 amSWF - MBJ
1 stop25h 05mMultiple Airlines
Sat 11/291:07 pmMBJ - SWF
1 stop20h 15mMultiple Airlines
Deal found 11/4$592
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/198:11 pmSWF - MBJ
2 stops15h 54mMultiple Airlines
Sun 12/281:05 pmMBJ - SWF
1 stop21h 42mMultiple Airlines
Deal found 11/6$608
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/209:45 amSWF - MBJ
2 stops26h 20mMultiple Airlines
Sun 12/281:05 pmMBJ - SWF
1 stop21h 42mMultiple Airlines
Deal found 11/3$620
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 12/228:25 pmSWF - MBJ
1 stop15h 40mMultiple Airlines
Wed 12/313:05 pmMBJ - SWF
1 stop19h 58mMultiple Airlines
Deal found 11/4$686

Cheap flight deals from Stewart to Montego Bay

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Montego Bay (MBJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$608
(Kiwi.com)

One-way from

$171
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$452
Provider with most accurate pricing for New Windsor Stewart-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Montego Bay Sangster Intl flights.
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From New Windsor Stewart to Montego Bay Sangster Intl
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One-way flight from New Windsor Stewart to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Montego Bay 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 November 6, 2025.
Use the filters below to find and compare flights from New Windsor to Montego Bay that are best for you.

Fly from

Stewart

Fly to

Montego Bay

Route

Depart

Return

Price

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 11/14

11:01 am-12:02 pm

1 stop25h 01m

Montego Bay Sangster Intl

Sun 11/16

1:07 pm-11:11 am

1 stop22h 04m

$439

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 11/24

10:57 am-12:02 pm

1 stop25h 05m

Montego Bay Sangster Intl

Sat 11/29

1:07 pm-9:22 am

1 stop20h 15m

$592

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 12/19

8:11 pm-12:05 pm

2 stops15h 54m

Montego Bay Sangster Intl

Sun 12/28

1:05 pm-10:47 am

1 stop21h 42m

$608

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sat 12/20

9:45 am-12:05 pm

2 stops26h 20m

Montego Bay Sangster Intl

Sun 12/28

1:05 pm-10:47 am

1 stop21h 42m

$620

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/22

8:25 pm-12:05 pm

1 stop15h 40m

Montego Bay Sangster Intl

Wed 12/31

3:05 pm-11:03 am

1 stop19h 58m

$686

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/15

12:27 pm-12:10 pm

1 stop23h 43m

$172

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 11/21

11:12 am-12:02 pm

1 stop24h 50m

$175

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 11/14

11:01 am-12:02 pm

1 stop25h 01m

$185

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 11/10

12:01 pm-12:02 pm

1 stop24h 01m

$201

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 11/24

10:57 am-12:02 pm

1 stop25h 05m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 12 results
1
2

Compare providers for flights from Stewart to Montego Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Montego Bay in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Montego Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Montego Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New Windsor-Montego Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Montego Bay flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Montego Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to Montego Bay

Have a flexible travel schedule? Discover the best time to fly to Montego Bay 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 Montego Bay

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Montego Bay (average of $158). Flying from New Windsor to Montego Bay 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 Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

  • How can I find direct flights from Stewart to Montego Bay?

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

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

    Yes. Cheapflights offers flight deals from Stewart to Montego Bay 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 Montego Bay?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Montego Bay (average of $158). Flying from New Windsor to Montego Bay 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

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Whitehouse
Lucea

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