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 52% 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.

What is the cheapest airline that flies from New Windsor Stewart to Caribbean Islands?

Breeze Airways is the most popular carrier operating from New Windsor Stewart to Caribbean Islands

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 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.

$184 Cheap Flights from New Windsor to Caribbean Islands in 2026

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0 bags

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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.

11:48 am - 11:38 pm

SWF

SJU

11h 50m

1 stop

5:12 pm - 9:18 am

SJU

SWF

16h 06m

1 stop

$365Multiple Airlines

Sun, Oct 4 - Wed, Oct 7

12:05 pm - 4:34 pm

SWF

SJU

28h 29m

1 stop

9:03 am - 10:16 am

SJU

SWF

25h 13m

1 stop

$370Multiple Airlines

Wed, Sep 2 - Thu, Sep 10

12:05 pm - 2:05 am

SWF

BQN

38h 00m

2 stops

10:52 am - 8:56 am

BQN

SWF

22h 04m

1 stop

$373Multiple Airlines

Sat, Aug 8 - Wed, Sep 16

12:05 pm - 1:54 am

SWF

SJU

13h 49m

2 stops

9:03 am - 10:16 am

SJU

SWF

25h 13m

1 stop

$376Multiple Airlines

Wed, Sep 2 - Thu, Sep 10

12:05 pm - 4:42 pm

SWF

SJU

28h 37m

1 stop

5:15 pm - 9:38 am

SJU

SWF

16h 23m

2 stops

$388Multiple Airlines

Sat, Aug 8 - Wed, Aug 12

12:39 pm - 11:57 pm

SWF

SJU

11h 18m

2 stops

5:12 pm - 9:18 am

SJU

SWF

16h 06m

1 stop

$395Multiple Airlines

Sat, Oct 3 - Wed, Oct 7

12:39 pm - 11:57 pm

SWF

SJU

11h 18m

2 stops

5:12 pm - 9:38 am

SJU

SWF

16h 26m

1 stop

$398Multiple Airlines

Sat, Sep 26 - Wed, Sep 30

12:05 pm - 4:34 pm

SWF

SJU

28h 29m

1 stop

6:42 pm - 8:56 am

SJU

SWF

14h 14m

1 stop

$399Multiple Airlines

Sat, Sep 5 - Sat, Sep 12

1:00 pm - 5:25 pm

SWF

SJU

28h 25m

2 stops

6:00 am - 6:41 pm

SJU

SWF

12h 41m

1 stop

$401Multiple Airlines

Sun, Aug 23 - Sun, Aug 30

12:26 pm - 1:50 am

SWF

SJU

13h 24m

2 stops

5:12 pm - 9:18 am

SJU

SWF

16h 06m

1 stop

$402Multiple Airlines

Fri, Oct 2 - Wed, Oct 7

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 10/4

11:48 am-11:38 pm

1 stop11h 50m

San Juan Luis Munoz Marin Intl

Wed 10/7

5:12 pm-9:18 am

1 stop16h 06m

$365

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 9/2

12:05 pm-4:34 pm

1 stop28h 29m

San Juan Luis Munoz Marin Intl

Thu 9/10

9:03 am-10:16 am

1 stop25h 13m

$370

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sat 8/8

12:05 pm-2:05 am

2 stops38h 00m

Aguadilla Borinquen

Wed 9/16

10:52 am-8:56 am

1 stop22h 04m

$373

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 9/2

12:05 pm-1:54 am

2 stops13h 49m

San Juan Luis Munoz Marin Intl

Thu 9/10

9:03 am-10:16 am

1 stop25h 13m

$376

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 8/8

12:05 pm-4:42 pm

1 stop28h 37m

San Juan Luis Munoz Marin Intl

Wed 8/12

5:15 pm-9:38 am

2 stops16h 23m

$388

Quickest round-trip

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 10/3

12:39 pm-11:57 pm

2 stops11h 18m

San Juan Luis Munoz Marin Intl

Wed 10/7

5:12 pm-9:18 am

1 stop16h 06m

$395

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 9/26

12:39 pm-11:57 pm

2 stops11h 18m

San Juan Luis Munoz Marin Intl

Wed 9/30

5:12 pm-9:38 am

1 stop16h 26m

$398

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 9/5

12:05 pm-4:34 pm

1 stop28h 29m

San Juan Luis Munoz Marin Intl

Sat 9/12

6:42 pm-8:56 am

1 stop14h 14m

$399

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 8/23

1:00 pm-5:25 pm

2 stops28h 25m

San Juan Luis Munoz Marin Intl

Sun 8/30

6:00 am-6:41 pm

1 stop12h 41m

$401

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 10/2

12:26 pm-1:50 am

2 stops13h 24m

San Juan Luis Munoz Marin Intl

Wed 10/7

5:12 pm-9:18 am

1 stop16h 06m

$402

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	6h 47m
Direct flights	None

The fastest flight from New Windsor to Caribbean Islands takes 6h 47m

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

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Frequently asked questions about flying from New Windsor to Caribbean Islands

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 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 (22.96% of total bookings). The next most popular plane models are Airbus A321neo (13.46%), Airbus A220-300 (10.74%), and Boeing 737 MAX 8 (9.58%).

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.