What airlines fly to Caribbean Islands?

JetBlue, United Airlines and Delta are the top three most popular airlines that fly to Caribbean Islands from New Windsor according to our data. JetBlue is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 13 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from New Windsor Stewart Airport to Caribbean Islands?

Prices for flights from New Windsor Stewart Airport to Caribbean Islands refresh daily.

How many operators does momondo search for flights from New Windsor Stewart Airport to Caribbean Islands?

There is 1 operator available for flights from New Windsor Stewart Airport to Caribbean Islands as of April 2026.

How old do you have to be to fly from New Windsor Stewart Airport to Caribbean Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New Windsor Stewart Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$111 Cheap Flights from New Windsor to Caribbean Islands in 2026

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Find the cheapest flights from New Windsor to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:45 am - 12:33 pm

SWF

SJU

24h 48m

1 stop

12:57 pm - 10:55 am

SJU

SWF

21h 58m

1 stop

$242Multiple Airlines

Sun, Apr 19 - Wed, Apr 22

11:45 am - 7:22 pm

SWF

SJU

7h 37m

1 stop

2:09 am - 10:55 am

SJU

SWF

32h 46m

2 stops

$255Multiple Airlines

Sun, Apr 19 - Tue, Apr 21

11:45 am - 12:23 pm

SWF

SJU

24h 38m

1 stop

2:09 am - 10:55 am

SJU

SWF

32h 46m

2 stops

$271Multiple Airlines

Thu, Apr 16 - Tue, Apr 21

11:45 am - 12:23 pm

SWF

SJU

24h 38m

1 stop

12:57 pm - 10:55 am

SJU

SWF

21h 58m

1 stop

$276Multiple Airlines

Thu, Apr 16 - Wed, Apr 22

11:45 am - 7:22 pm

SWF

SJU

7h 37m

1 stop

12:57 pm - 10:55 am

SJU

SWF

21h 58m

1 stop

$280Multiple Airlines

Thu, Apr 16 - Wed, Apr 22

11:45 am - 7:22 pm

SWF

SJU

7h 37m

1 stop

7:01 pm - 10:55 am

SJU

SWF

15h 54m

2 stops

$291Multiple Airlines

Sun, Apr 19 - Wed, Apr 22

11:45 am - 7:22 pm

SWF

SJU

7h 37m

1 stop

7:01 pm - 10:55 am

SJU

SWF

15h 54m

2 stops

$315Multiple Airlines

Thu, Apr 23 - Sat, Apr 25

11:45 am - 8:49 am

SWF

SJU

21h 04m

2 stops

8:30 am - 11:25 am

SJU

SWF

26h 55m

1 stop

$321Multiple Airlines

Thu, Apr 30 - Tue, May 5

11:45 am - 7:22 pm

SWF

SJU

7h 37m

1 stop

8:27 pm - 10:50 am

SJU

SWF

14h 23m

1 stop

$322Multiple Airlines

Sun, Apr 26 - Thu, Apr 30

11:45 am - 7:22 pm

SWF

SJU

7h 37m

1 stop

7:01 pm - 10:55 am

SJU

SWF

15h 54m

2 stops

$339Multiple Airlines

Thu, Apr 16 - Wed, Apr 22

momondo 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

Cheapest round-trip

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/19

11:45 am-12:33 pm

1 stop24h 48m

San Juan Luis Munoz Marin Intl

Wed 4/22

12:57 pm-10:55 am

1 stop21h 58m

$242

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/19

11:45 am-7:22 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Tue 4/21

2:09 am-10:55 am

2 stops32h 46m

$255

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/16

11:45 am-12:23 pm

1 stop24h 38m

San Juan Luis Munoz Marin Intl

Tue 4/21

2:09 am-10:55 am

2 stops32h 46m

$271

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/16

11:45 am-12:23 pm

1 stop24h 38m

San Juan Luis Munoz Marin Intl

Wed 4/22

12:57 pm-10:55 am

1 stop21h 58m

$276

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/16

11:45 am-7:22 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Wed 4/22

12:57 pm-10:55 am

1 stop21h 58m

$280

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/19

11:45 am-7:22 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Wed 4/22

7:01 pm-10:55 am

2 stops15h 54m

$291

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/23

11:45 am-7:22 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Sat 4/25

7:01 pm-10:55 am

2 stops15h 54m

$315

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/30

11:45 am-8:49 am

2 stops21h 04m

San Juan Luis Munoz Marin Intl

Tue 5/5

8:30 am-11:25 am

1 stop26h 55m

$321

Quickest round-trip

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 4/26

11:45 am-7:22 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Thu 4/30

8:27 pm-10:50 am

1 stop14h 23m

$322

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 4/16

11:45 am-7:22 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Wed 4/22

7:01 pm-10:55 am

2 stops15h 54m

$339

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from New Windsor to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Can stopping save me money on New Windsor to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between New Windsor to Caribbean Islands.

Cheap New Windsor to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Windsor to Caribbean Islands

Fastest flight time	7h 20m
Direct flights	None

The fastest flight from New Windsor to Caribbean Islands takes 7h 20m

There are no direct flights from New Windsor to Caribbean Islands. There are no popular flight routes from New Windsor to Caribbean Islands.

Search flight deals

When did momondo last update prices for flights from New Windsor Stewart Airport to Caribbean Islands?
Prices for flights from New Windsor Stewart Airport to Caribbean Islands refresh daily.
How many operators does momondo search for flights from New Windsor Stewart Airport to Caribbean Islands?
There is 1 operator available for flights from New Windsor Stewart Airport to Caribbean Islands as of April 2026.
How old do you have to be to fly from New Windsor Stewart Airport to Caribbean Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New Windsor Stewart Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from New Windsor to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from New Windsor to Caribbean Islands is Airbus A320-100/200 (23.45% of total bookings). The next most popular plane models are Airbus A321neo (13.83%), Boeing 737 MAX 8 (9.98%), and Airbus A220-300 (9.96%).

Best airlines flying from New Windsor to Caribbean Islands

Compare and see reviews for airlines that fly from New Windsor to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $227	Free Cancellation	Rating 7.2 2,908 reviews		Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from New Windsor to Caribbean Islands?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New Windsor to Caribbean Islands. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from New Windsor to Caribbean Islands with flexible booking policies on momondo?

Flights from New Windsor to Caribbean Islands with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from New Windsor to Caribbean Islands?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from New Windsor.

I’m not ready to book a flight from New Windsor to Caribbean Islands right now. Can momondo alert me if prices change?

Yes. momondo can track prices for New Windsor to Caribbean Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.