What are the most popular routes from New Windsor to Caribbean Islands?

Most travelers choose New Windsor Stewart - San Juan Luis Munoz Marin Intl, New Windsor Stewart - Nassau Intl or New Windsor Stewart - Montego Bay Sangster Intl when deciding on the best route from New Windsor to Caribbean Islands.

How far in advance should I book a flight from New Windsor to Caribbean Islands?

Find a great deal and save up to 30% by booking at least 57 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from New Windsor to Caribbean Islands within the next two weeks, with the cheapest ticket starting at $247.

What is the cheapest month to fly from New Windsor to Caribbean Islands?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, September can be a great choice for travel to Caribbean Islands. Flights to Caribbean Islands from New Windsor in September are about $272 on average during September, but can be found for as low as $91.

What airport do you fly from for flights from New Windsor to Caribbean Islands?

For a flight from New Windsor to Caribbean Islands, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

Can I find deals for flights from Stewart to Caribbean Islands that include hotel bookings?

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

How can I find direct flights from Stewart to Caribbean Islands?

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

Can I find deals for business class flights from Stewart to Caribbean Islands?

Yes. Cheapflights offers flight deals from Stewart to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$114+ Flights from New Windsor to Caribbean Islands

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Cheap flight deals from Stewart to Caribbean Islands

Round-trip from	$253 (Mytrip)
One-way from	$114 (Mytrip)
Popular in	December
Cheapest in	September
Average price	$341

From New Windsor Stewart to Caribbean Islands

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One-way flight from New Windsor Stewart to Caribbean Islands

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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).

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Average for round-trip flights in April 2025

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Find flight deals from Stewart to Caribbean Islands

Cheapest flights from Stewart to Caribbean Islands
Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.

Fri 5/1611:55 amSWF - SJU

2 stops34h 43mMultiple Airlines

Thu 5/228:12 pmSJU - SWF

1 stop14h 53mMultiple Airlines

Deal found 4/9

$253

Fri 5/211:50 amSWF - AUA

1 stop26h 50mMultiple Airlines

Thu 5/83:45 pmAUA - SWF

1 stop19h 15mMultiple Airlines

Deal found 4/10

$329

Mon 5/511:50 amSWF - PUJ

1 stop26h 52mMultiple Airlines

Thu 5/83:22 pmPUJ - SWF

1 stop19h 38mMultiple Airlines

Deal found 4/9

$330

Fri 5/911:50 amSWF - MBJ

1 stop24h 12mMultiple Airlines

Thu 5/1512:07 pmMBJ - SWF

1 stop21h 58mMultiple Airlines

Deal found 4/10

$361

Fri 5/911:50 amSWF - NAS

1 stop7h 25mMultiple Airlines

Sun 5/114:00 pmNAS - SWF

1 stop19h 00mMultiple Airlines

Deal found 4/10

$432

Fri 5/211:50 amSWF - SDQ

1 stop26h 56mMultiple Airlines

Sun 5/48:55 amSDQ - SWF

2 stops26h 05mMultiple Airlines

Deal found 4/9

$504

Fri 8/17:56 pmSWF - KIN

1 stop16h 20mMultiple Airlines

Mon 8/117:05 amKIN - SWF

1 stop11h 01mMultiple Airlines

Deal found 4/10

$539

Fri 7/47:56 pmSWF - CUR

1 stop15h 39mMultiple Airlines

Mon 7/74:25 pmCUR - SWF

2 stops19h 31mMultiple Airlines

Deal found 4/10

$680

Best flights from Stewart to Caribbean Islands
Discover carefully curated flight deals from Stewart to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 11, 2025.

Fri 5/1611:55 amSWF - SJU

2 stops34h 43mMultiple Airlines

Thu 5/228:12 pmSJU - SWF

1 stop14h 53mMultiple Airlines

Deal found 4/9

$253

Mon 5/1211:50 amSWF - PUJ

1 stop26h 27mMultiple Airlines

Thu 5/153:22 pmPUJ - SWF

1 stop19h 43mMultiple Airlines

Deal found 4/9

$314

Fri 5/211:50 amSWF - AUA

1 stop26h 50mMultiple Airlines

Thu 5/83:45 pmAUA - SWF

1 stop19h 15mMultiple Airlines

Deal found 4/10

$329

Mon 4/2811:50 amSWF - MBJ

1 stop24h 05mMultiple Airlines

Thu 5/112:00 pmMBJ - SWF

1 stop22h 00mMultiple Airlines

Deal found 4/9

$331

Mon 5/1211:50 amSWF - KIN

1 stop25h 39mMultiple Airlines

Thu 5/151:34 pmKIN - SWF

1 stop20h 31mMultiple Airlines

Deal found 4/9

$369

Mon 6/97:18 pmSWF - NAS

1 stop23h 57mMultiple Airlines

Fri 6/1311:30 amNAS - SWF

1 stop6h 58mMultiple Airlines

Deal found 4/9

$420

Fri 5/911:50 amSWF - SDQ

1 stop26h 45mMultiple Airlines

Sun 5/118:55 amSDQ - SWF

2 stops26h 05mMultiple Airlines

Deal found 4/9

$497

Fri 7/47:56 pmSWF - CUR

1 stop15h 39mMultiple Airlines

Mon 7/74:25 pmCUR - SWF

2 stops19h 31mMultiple Airlines

Deal found 4/10

$680

Fri 4/2511:50 amSWF - SXM

1 stop26h 10mMultiple Airlines

Sun 4/277:10 amSXM - SWF

3 stops27h 50mMultiple Airlines

Deal found 4/9

$765

Last-minute flights from Stewart to Caribbean Islands
Discover last-minute flight deals from Stewart to Caribbean Islands. Data last updated April 11, 2025 and is based on user searches.

Thu 4/177:54 pmSWF - NAS

1 stop20h 31mMultiple Airlines

Thu 4/2412:00 pmNAS - SWF

1 stop7h 14mMultiple Airlines

Deal found 4/10

$693

Thu 4/177:54 pmSWF - SDQ

1 stop14h 17mMultiple Airlines

Thu 4/245:20 amSDQ - SWF

2 stops13h 54mMultiple Airlines

Deal found 4/10

$800

Fri 4/1811:50 amSWF - SJU

2 stops23h 12mMultiple Airlines

Sat 4/2612:54 amSJU - SWF

2 stops34h 06mMultiple Airlines

Deal found 4/10

$480

Sun 4/207:54 pmSWF - MBJ

2 stops17h 51mMultiple Airlines

Thu 4/2412:00 pmMBJ - SWF

1 stop22h 00mMultiple Airlines

Deal found 4/10

$562

Sun 4/207:54 pmSWF - CUR

3 stops42h 46mMultiple Airlines

Sun 5/1110:05 amCUR - SWF

2 stops24h 55mMultiple Airlines

Deal found 4/9

$776

Mon 4/2111:50 amSWF - PUJ

1 stop26h 52mMultiple Airlines

Thu 4/243:48 pmPUJ - SWF

1 stop19h 12mMultiple Airlines

Deal found 4/9

$367

Fri 5/211:50 amSWF - AUA

1 stop26h 50mMultiple Airlines

Thu 5/83:45 pmAUA - SWF

1 stop19h 15mMultiple Airlines

Deal found 4/10

$329

Fri 5/211:50 amSWF - SDQ

1 stop26h 56mMultiple Airlines

Sun 5/48:55 amSDQ - SWF

2 stops26h 05mMultiple Airlines

Deal found 4/9

$504

Mon 5/511:50 amSWF - PUJ

1 stop26h 52mMultiple Airlines

Thu 5/83:22 pmPUJ - SWF

1 stop19h 38mMultiple Airlines

Deal found 4/9

$330

Fri 5/911:50 amSWF - MBJ

1 stop24h 12mMultiple Airlines

Thu 5/1512:07 pmMBJ - SWF

1 stop21h 58mMultiple Airlines

Deal found 4/10

$361

Fri 5/911:50 amSWF - NAS

1 stop7h 25mMultiple Airlines

Sun 5/114:00 pmNAS - SWF

1 stop19h 00mMultiple Airlines

Deal found 4/10

$432

Fri 5/1611:55 amSWF - SJU

2 stops34h 43mMultiple Airlines

Thu 5/228:12 pmSJU - SWF

1 stop14h 53mMultiple Airlines

Deal found 4/9

$253

One-way flights from Stewart to Caribbean Islands
Search for one-way flight options from Stewart to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 11, 2025.

Mon 5/1911:55 amSWF - SJU

2 stops23h 36mMultiple Airlines

Deal found 4/9

$114

Fri 5/3011:55 amSWF - AUA

1 stop26h 45mMultiple Airlines

Deal found 4/9

$130

Fri 5/1611:55 amSWF - MBJ

1 stop24h 07mMultiple Airlines

Deal found 4/9

$139

Mon 5/511:50 amSWF - KIN

1 stop25h 41mMultiple Airlines

Deal found 4/10

$140

Fri 4/2511:50 amSWF - PUJ

1 stop26h 23mMultiple Airlines

Deal found 4/10

$144

Fri 5/1611:55 amSWF - SXM

1 stop26h 05mMultiple Airlines

Deal found 4/10

$145

Fri 5/211:50 amSWF - NAS

1 stop7h 25mMultiple Airlines

Deal found 4/10

$156

Fri 4/2511:50 amSWF - SDQ

1 stop26h 56mMultiple Airlines

Deal found 4/10

$169

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 5/16

11:55 am-10:38 pm

2 stops34h 43m

San Juan Luis Munoz Marin Intl

Thu 5/22

8:12 pm-11:05 am

1 stop14h 53m

$253

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Fri 5/2

11:50 am-2:40 pm

1 stop26h 50m

Oranjestad Reina Beatrix

Thu 5/8

3:45 pm-11:00 am

1 stop19h 15m

$329

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 5/5

11:50 am-2:42 pm

1 stop26h 52m

Punta Cana

Thu 5/8

3:22 pm-11:00 am

1 stop19h 38m

$330

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 5/9

11:50 am-11:02 am

1 stop24h 12m

Montego Bay Sangster Intl

Thu 5/15

12:07 pm-11:05 am

1 stop21h 58m

$361

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Fri 5/9

11:50 am-7:15 pm

1 stop7h 25m

Nassau Intl

Sun 5/11

4:00 pm-11:00 am

1 stop19h 00m

$432

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 5/2

11:50 am-2:46 pm

1 stop26h 56m

Santo Domingo Las Americas

Sun 5/4

8:55 am-11:00 am

2 stops26h 05m

$504

New WindsorWillemstad

SWF - CUR

SWFCUR

New Windsor Stewart

Fri 7/4

7:56 pm-11:35 am

1 stop15h 39m

Willemstad Hato Int.

Mon 7/7

4:25 pm-11:56 am

2 stops19h 31m

$680

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 5/19

11:55 am-11:31 am

2 stops23h 36m

$114

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Fri 5/9

11:50 am-2:40 pm

1 stop26h 50m

$137

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Mon 5/5

11:50 am-12:31 pm

1 stop25h 41m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

Showing 1-10 of 15 results

Best time to book a flight from Stewart to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Caribbean Islands

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

Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands in December is currently the most expensive (average of $336). 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.

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

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

Rainfall in Caribbean Islands by month

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June 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).

Related info for your journey

What airport do you fly from for flights from New Windsor to Caribbean Islands?
For a flight from New Windsor to Caribbean Islands, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.
What are the most popular routes from New Windsor to Caribbean Islands?
Most travelers choose New Windsor Stewart - San Juan Luis Munoz Marin Intl, New Windsor Stewart - Nassau Intl or New Windsor Stewart - Montego Bay Sangster Intl when deciding on the best route from New Windsor to Caribbean Islands.
Can I find deals for flights from Stewart to Caribbean Islands that include hotel bookings?
Yes. In addition to deals on Stewart to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to Caribbean Islands?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Caribbean Islands.
Can I find deals for business class flights from Stewart to Caribbean Islands?
Yes. Cheapflights offers flight deals from Stewart to Caribbean Islands 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 Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands in December is currently the most expensive (average of $336). 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

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Stewart to Caribbean Islands

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$90	Average$186	FlexibilityNo cancel fee	On-time62%
JetBlue	Cheapest$175	Average$338	FlexibilityNo cancel fee	On-time62%

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$114+ Cheap flights from New Windsor (SWF) to Caribbean Islands

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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Caribbean Islands with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to Caribbean Islands

Keep the following information in mind while searching for Stewart to Caribbean Islands flight deals. Data was last updated April 11, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Stewart to Caribbean Islands

Cheapest flights from Stewart to Caribbean IslandsExplore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.

Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Stewart to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Stewart with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Caribbean Islands

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

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

Find hourly flight availability from Stewart to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 11, 2025.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Caribbean Islands. 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 from for flights from New Windsor to Caribbean Islands?

What are the most popular routes from New Windsor to Caribbean Islands?

Can I find deals for flights from Stewart to Caribbean Islands that include hotel bookings?

How can I find direct flights from Stewart to Caribbean Islands?

Can I find deals for business class flights from Stewart to Caribbean Islands?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Caribbean Islands

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

Top 2 airlines flying from Stewart to Caribbean Islands

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Cheapest flights from Stewart to Caribbean Islands
Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.