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Montego Bay

$327+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/2311:43 amSWF - MBJ
1 stop26h 14mMultiple Airlines
Sun 1/1112:57 pmMBJ - SWF
1 stop21h 22mMultiple Airlines
Deal found 12/10$573
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/157:30 pmSWF - MBJ
2 stops16h 40mMultiple Airlines
Thu 12/181:05 pmMBJ - SWF
1 stop29h 01mMultiple Airlines
Deal found 12/10$610
This Kiwi.com deal was found by Cheapflights users on 12/10. 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
2 stops41h 32mMultiple Airlines
Mon 12/293:05 pmMBJ - SWF
1 stop19h 58mMultiple Airlines
Deal found 12/10$633
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/2311:43 amSWF - MBJ
1 stop26h 14mMultiple Airlines
Sun 12/281:05 pmMBJ - SWF
1 stop21h 42mMultiple Airlines
Deal found 12/10$670
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/2311:43 amSWF - MBJ
1 stop26h 14mMultiple Airlines
Tue 12/301:05 pmMBJ - SWF
2 stops27h 39mMultiple Airlines
Deal found 12/10$671
This Kiwi.com deal was found by Cheapflights users on 12/11. 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
2 stops41h 32mMultiple Airlines
Thu 1/11:05 pmMBJ - SWF
1 stop22h 02mMultiple Airlines
Deal found 12/11$837
This Kiwi.com deal was found by Cheapflights users on 12/11. 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
2 stops41h 32mMultiple Airlines
Sun 1/41:05 pmMBJ - SWF
1 stop21h 42mMultiple Airlines
Deal found 12/11$873
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/245:34 pmSWF - MBJ
2 stops18h 31mMultiple Airlines
Sun 1/41:05 pmMBJ - SWF
1 stop21h 42mMultiple Airlines
Deal found 12/11$886
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/2111:43 amSWF - MBJ
1 stop26h 14mMultiple Airlines
Sun 1/41:05 pmMBJ - SWF
1 stop21h 42mMultiple Airlines
Deal found 12/11$905

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$573
(Kiwi.com)

One-way from

$327
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$694
Provider with most accurate pricing for New Windsor Stewart-Montego Bay Sangster Intl flight deals.
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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
Search Deals
One-way flight from New Windsor Stewart to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 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

Tue 12/23

11:43 am-1:57 pm

1 stop26h 14m

Montego Bay Sangster Intl

Sun 1/11

12:57 pm-10:19 am

1 stop21h 22m

$573

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/15

7:30 pm-12:10 pm

2 stops16h 40m

Montego Bay Sangster Intl

Thu 12/18

1:05 pm-6:06 pm

1 stop29h 01m

$610

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/22

8:25 pm-1:57 pm

2 stops41h 32m

Montego Bay Sangster Intl

Mon 12/29

3:05 pm-11:03 am

1 stop19h 58m

$633

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Wed 12/24

5:34 pm-12:05 pm

2 stops18h 31m

Montego Bay Sangster Intl

Sun 1/11

12:57 pm-10:19 am

1 stop21h 22m

$633

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Tue 12/23

11:43 am-1:57 pm

1 stop26h 14m

Montego Bay Sangster Intl

Sun 12/28

1:05 pm-10:47 am

1 stop21h 42m

$670

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Tue 12/23

11:43 am-1:57 pm

1 stop26h 14m

Montego Bay Sangster Intl

Tue 12/30

1:05 pm-4:44 pm

2 stops27h 39m

$671

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/22

8:25 pm-1:57 pm

2 stops41h 32m

Montego Bay Sangster Intl

Thu 1/1

1:05 pm-11:07 am

1 stop22h 02m

$837

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 12/22

8:25 pm-1:57 pm

2 stops41h 32m

Montego Bay Sangster Intl

Sun 1/4

1:05 pm-10:47 am

1 stop21h 42m

$873

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Wed 12/24

5:34 pm-12:05 pm

2 stops18h 31m

Montego Bay Sangster Intl

Sun 1/4

1:05 pm-10:47 am

1 stop21h 42m

$886

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Mon 1/19

11:09 am-11:15 am

2 stops24h 06m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 15 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 December.
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 $159). 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 $159). 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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