In terms of precipitation, rainfall in Montego Bay ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Montego Bay when rainfall is around 1.6 in.

If weather is an important factor for your trip to Montego Bay, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

What is the cheapest time of day to fly from SWF to MBJ?

When flying from New Windsor to Montego Bay, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

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.

$171+ Flights from New Windsor to Montego Bay

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1. Tell us where you want to go

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Cheap flight deals from Stewart to Montego Bay

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$539 (Kiwi.com)
One-way from	$171 (Kiwi.com)
Popular in	December
Cheapest in	March
Average price	$435

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

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One-way flight from New Windsor Stewart to Montego Bay Sangster Intl

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Highest demand for flights based on searches. 0% potential increase in price ($0 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

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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 January 15, 2026.

Thu 4/1611:45 am

SWF

MBJ

1 stop24h 17m

Multiple Airlines

Tue 4/211:25 pm

MBJ

SWF

2 stops44h 30m

Multiple Airlines

Deal found 1/15

$539

Best flights from Stewart to Montego Bay
Discover carefully curated flight deals from Stewart to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 15, 2026.

Thu 4/1611:45 am

SWF

MBJ

1 stop24h 17m

Multiple Airlines

Tue 4/211:25 pm

MBJ

SWF

2 stops44h 30m

Multiple Airlines

Deal found 1/15

$539

One-way flights from Stewart to Montego Bay
Search for one-way flight options from Stewart to Montego Bay. Find affordable one-way fares based on user searches. Data last updated January 15, 2026.

Thu 3/510:09 am

SWF

MBJ

1 stop25h 53m

Multiple Airlines

Deal found 1/14

$171

Sun 3/810:09 am

SWF

MBJ

1 stop25h 53m

Multiple Airlines

Deal found 1/13

$176

Thu 2/1912:22 pm

SWF

MBJ

1 stop23h 40m

Multiple Airlines

Deal found 1/14

$181

Wed 2/185:46 pm

SWF

MBJ

2 stops18h 16m

Multiple Airlines

Deal found 1/13

$208

Sun 4/510:29 am

SWF

MBJ

1 stop25h 29m

Multiple Airlines

Deal found 1/13

$217

Thu 1/2212:13 pm

SWF

MBJ

2 stops23h 49m

Multiple Airlines

Deal found 1/13

$225

Wed 2/115:46 pm

SWF

MBJ

2 stops18h 16m

Multiple Airlines

Deal found 1/15

$293

Sun 1/1812:13 pm

SWF

MBJ

2 stops23h 49m

Multiple Airlines

Deal found 1/13

$317

Mon 3/3012:11 pm

SWF

MBJ

3 stops23h 47m

Multiple Airlines

Deal found 1/13

$360

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 4/16

11:45 am-11:02 am

1 stop24h 17m

Montego Bay Sangster Intl

Tue 4/21

1:25 pm-10:55 am

2 stops44h 30m

$539

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 3/5

10:09 am-12:02 pm

1 stop25h 53m

$171

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 3/8

10:09 am-11:02 am

1 stop25h 53m

$176

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 3/22

10:29 am-10:58 am

1 stop25h 29m

$176

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 2/19

12:22 pm-12:02 pm

1 stop23h 40m

$181

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Wed 2/18

5:46 pm-12:02 pm

2 stops18h 16m

$209

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Thu 1/22

12:13 pm-12:02 pm

2 stops23h 49m

$225

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 4/5

11:48 am-10:58 am

2 stops24h 10m

$247

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Wed 2/11

5:46 pm-12:02 pm

2 stops18h 16m

$293

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 1/18

12:13 pm-12:02 pm

2 stops23h 49m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 11 results

Compare providers for flights from Stewart to Montego Bay

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 January.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust 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, March is the cheapest month in which you can book a flight from New Windsor to Montego Bay (average of $171). 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

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, March is the cheapest month in which you can book a flight from New Windsor to Montego Bay (average of $171). 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

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Alternative routes for Stewart to Montego Bay

Complete your trip

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$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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Montego Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to Montego Bay

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Stewart to Montego Bay

Cheapest flights from Stewart to Montego BayExplore 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 January 15, 2026.

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 January 15, 2026.

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Montego Bay that are best for you.

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 January.

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.

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?

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?

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

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

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

Traveling to a place near Montego Bay?

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Alternative routes for Stewart to Montego Bay

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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 January 15, 2026.