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 12 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 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.

$99 Cheap Flights from New Windsor to Caribbean Islands in 2026

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.

10:18 am - 11:38 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 20m1 stop Fort Lauderdale

5:12 pm - 9:48 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

16h 36m1 stop Fort Lauderdale

$184Multiple Airlines

Thu, Oct 15 - Wed, Oct 28

10:18 am - 11:38 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 20m1 stop Fort Lauderdale

5:12 pm - 11:08 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

17h 56m1 stop Fort Lauderdale

$190Multiple Airlines

Thu, Oct 15 - Sat, Oct 24

10:38 am - 11:38 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 00m1 stop Fort Lauderdale

5:12 pm - 12:08 pmSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

18h 56m1 stop Fort Lauderdale

$201Multiple Airlines

Thu, Oct 29 - Sat, Oct 31

10:38 am - 11:38 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 00m1 stop Fort Lauderdale

6:12 pm - 10:10 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

16h 58m1 stop Fort Lauderdale

$202Multiple Airlines

Thu, Oct 29 - Wed, Nov 4

10:18 am - 1:31 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

27h 13m1 stop Fort Lauderdale

8:45 am - 9:48 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

25h 03m1 stop Fort Lauderdale

$215Multiple Airlines

Thu, Oct 15 - Wed, Oct 21

11:53 am - 1:31 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

25h 38m1 stop Fort Lauderdale

8:45 am - 9:48 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

25h 03m1 stop Fort Lauderdale

$221Multiple Airlines

Sun, Oct 18 - Wed, Oct 21

10:18 am - 1:31 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

27h 13m1 stop Fort Lauderdale

8:45 am - 9:48 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

25h 03m1 stop Fort Lauderdale

$223Multiple Airlines

Thu, Oct 15 - Wed, Oct 21

10:28 am - 1:34 pmSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

27h 06m1 stop Fort Lauderdale

8:45 am - 9:28 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

24h 43m1 stop Fort Lauderdale

$229Multiple Airlines

Thu, Oct 1 - Wed, Oct 7

12:16 pm - 10:14 amSWF New Windsor Stewart-BQN Aguadilla Borinquen

21h 58m2 stops Charleston Orlando

11:08 am - 10:16 amBQN Aguadilla Borinquen-SWF New Windsor Stewart

23h 08m1 stop Orlando

$352Multiple Airlines

Fri, Sep 11 - Thu, Sep 17

11:06 am - 10:14 amSWF New Windsor Stewart-BQN Aguadilla Borinquen

23h 08m1 stop Orlando Sanford Intl

11:08 am - 10:16 amBQN Aguadilla Borinquen-SWF New Windsor Stewart

23h 08m1 stop Orlando

$355Multiple Airlines

Fri, Sep 11 - Thu, Sep 17

Cheap last minute flights

Enter your travel dates to find the best prices.

12:05 pm - 8:11 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

20h 06m2 stops Raleigh-Durham Orlando

6:35 am - 12:10 pmSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

29h 35m1 stop Fort Lauderdale

$440Multiple Airlines

Wed, Aug 19 - Sat, Aug 22

12:17 pm - 2:15 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 58m2 stops Charleston Orlando

8:57 pm - 9:53 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

12h 56m1 stop Orlando

$477Multiple Airlines

Fri, Aug 21 - Wed, Aug 26

10:33 am - 2:15 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

15h 42m1 stop Orlando

3:55 pm - 10:31 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

18h 36m1 stop Orlando

$480Multiple Airlines

Thu, Aug 20 - Sun, Sep 20

5:39 pm - 8:11 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

14h 32m1 stop Orlando Sanford Intl

6:35 am - 6:41 pmSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

12h 06m1 stop Fort Lauderdale

$486Multiple Airlines

Fri, Aug 21 - Thu, Aug 27

10:33 am - 2:15 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

15h 42m1 stop Orlando

8:57 pm - 9:53 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

12h 56m1 stop Orlando

$509Multiple Airlines

Thu, Aug 20 - Wed, Aug 26

12:17 pm - 2:15 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 58m2 stops Charleston Orlando

8:57 pm - 9:53 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

12h 56m1 stop Orlando

$570Multiple Airlines

Fri, Aug 21 - Sat, Aug 22

11:17 am - 12:34 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 17m1 stop Tampa St. Petersburg

12:11 pm - 11:37 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

23h 26m2 stops Orlando Charleston

$580Multiple Airlines

Thu, Aug 20 - Sun, Aug 23

11:17 am - 12:34 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 17m1 stop Tampa St. Petersburg

5:37 pm - 10:27 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

16h 50m1 stop Tampa

$608Multiple Airlines

Thu, Aug 20 - Sat, Aug 22

12:17 pm - 2:15 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

13h 58m2 stops Charleston Orlando

8:57 pm - 11:08 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

14h 11m1 stop Orlando

$609Multiple Airlines

Fri, Aug 21 - Mon, Aug 31

5:39 pm - 8:11 amSWF New Windsor Stewart-SJU San Juan Luis Munoz Marin Intl

14h 32m1 stop Orlando Sanford Intl

8:57 pm - 11:37 amSJU San Juan Luis Munoz Marin Intl-SWF New Windsor Stewart

14h 40m2 stops Orlando Charleston

$614Multiple Airlines

Fri, Aug 21 - Sun, Aug 23

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Breeze Airways flights from New Windsor to Caribbean Islands

Our best Breeze Airways deals on New Windsor to Caribbean Islands flight tickets

Breeze Airways

Sep 5

SWF12:05 pmNew Windsor Stewart

20h 50m

2 stops

NAS8:55 amNassau Intl

Sep 11

NAS9:25 amNassau Intl

26h 14m

2 stops

SWF11:39 amNew Windsor Stewart

$880

Breeze Airways

Sep 5

SWF12:05 pmNew Windsor Stewart

20h 50m

2 stops

NAS8:55 amNassau Intl

Sep 11

NAS9:25 amNassau Intl

26h 14m

2 stops

SWF11:39 amNew Windsor Stewart

$903

Breeze Airways

Aug 29

SWF12:05 pmNew Windsor Stewart

20h 50m

2 stops

NAS8:55 amNassau Intl

Sep 4

NAS9:55 amNassau Intl

25h 30m

2 stops

SWF11:25 amNew Windsor Stewart

$964

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

Quickest round-trip

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-11:38 pm

1 stop13h 20m

San Juan Luis Munoz Marin Intl

Wed 10/28

5:12 pm-9:48 am

1 stop16h 36m

$184

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-11:38 pm

1 stop13h 20m

San Juan Luis Munoz Marin Intl

Sat 10/24

5:12 pm-11:08 am

1 stop17h 56m

$190

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/29

10:38 am-11:38 pm

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Sat 10/31

5:12 pm-12:08 pm

1 stop18h 56m

$201

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/29

10:38 am-11:38 pm

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Wed 11/4

6:12 pm-10:10 am

1 stop16h 58m

$202

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-1:31 pm

1 stop27h 13m

San Juan Luis Munoz Marin Intl

Wed 10/21

8:45 am-9:48 am

1 stop25h 03m

$215

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Sun 10/18

11:53 am-1:31 pm

1 stop25h 38m

San Juan Luis Munoz Marin Intl

Wed 10/21

8:45 am-9:48 am

1 stop25h 03m

$221

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-1:31 pm

1 stop27h 13m

San Juan Luis Munoz Marin Intl

Wed 10/21

8:45 am-9:48 am

1 stop25h 03m

$223

New WindsorSan Juan

SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl

SWFSJU

New Windsor Stewart

Thu 10/1

10:28 am-1:34 pm

1 stop27h 06m

San Juan Luis Munoz Marin Intl

Wed 10/7

8:45 am-9:28 am

1 stop24h 43m

$229

New WindsorAguadilla

SWF New Windsor Stewart - BQN Aguadilla Borinquen

SWFBQN

New Windsor Stewart

Fri 9/11

12:16 pm-10:14 am

2 stops21h 58m

Aguadilla Borinquen

Thu 9/17

11:08 am-10:16 am

1 stop23h 08m

$352

New WindsorAguadilla

SWF New Windsor Stewart - BQN Aguadilla Borinquen

SWFBQN

New Windsor Stewart

Fri 9/11

11:06 am-10:14 am

1 stop23h 08m

Aguadilla Borinquen

Thu 9/17

11:08 am-10:16 am

1 stop23h 08m

$355

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 15m
Direct flights	None

The fastest flight from New Windsor to Caribbean Islands takes 7h 15m

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

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 (21.13% of total bookings). The next most popular plane models are Airbus A321-100/200 (12.54%), Boeing 737 MAX 8 (11.92%), and Airbus A220-300 (11.83%).

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.