What airlines fly to Caribbean?

JetBlue, United Airlines and Delta are the top three most popular airlines that fly to Caribbean from New Windsor according to our data. JetBlue is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 13 different airlines that fly to Caribbean 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?

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

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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.

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

The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$122 Cheap Flights from New Windsor to Caribbean in 2025/26

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0 bags

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Find the cheapest flights from New Windsor to Caribbean

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Cheap round-trip flights

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12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

4:10 am - 11:37 amSJU-SWF

8h 27m1 stop

$248Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

4:10 am - 11:37 amSJU-SWF

8h 27m1 stop

$249Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

4:10 am - 6:06 pmSJU-SWF

14h 56m1 stop

$265Multiple Airlines

Find Deal

Mon, Dec 15 - Thu, Dec 18

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

4:10 am - 11:37 amSJU-SWF

8h 27m1 stop

$271Multiple Airlines

Find Deal

Fri, Dec 12 - Sun, Dec 14

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

11:38 am - 11:37 amSJU-SWF

24h 59m2 stops

$275Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

5:00 pm - 11:37 amSJU-SWF

19h 37m2 stops

$281Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

5:00 pm - 11:37 amSJU-SWF

19h 37m2 stops

$282Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

12:27 pm - 12:49 amSWF-SJU

35h 22m2 stops

4:10 am - 11:37 amSJU-SWF

8h 27m1 stop

$285Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

1:27 pm - 11:37 amSJU-SWF

23h 10m2 stops

$287Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

12:27 pm - 12:45 amSWF-SJU

11h 18m1 stop

5:00 pm - 11:37 amSJU-SWF

19h 37m2 stops

$292Multiple Airlines

Find Deal

Mon, Dec 8 - Thu, Dec 11

Fly from

Fly to

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

4:10 am-11:37 am

1 stop8h 27m

$248

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

4:10 am-11:37 am

1 stop8h 27m

$249

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/15

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/18

4:10 am-6:06 pm

1 stop14h 56m

$265

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 12/12

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Sun 12/14

4:10 am-11:37 am

1 stop8h 27m

$271

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

11:38 am-11:37 am

2 stops24h 59m

$275

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

5:00 pm-11:37 am

2 stops19h 37m

$281

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

5:00 pm-11:37 am

2 stops19h 37m

$282

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:49 am

2 stops35h 22m

San Juan Luis Munoz Marin Intl

Thu 12/11

4:10 am-11:37 am

1 stop8h 27m

$285

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

1:27 pm-11:37 am

2 stops23h 10m

$287

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/11

5:00 pm-11:37 am

2 stops19h 37m

$292

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

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

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from New Windsor to Caribbean is on a Wednesday when prices can be found for as low as $170. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $449. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the afternoon is the cheapest time of day to fly from New Windsor to Caribbean when you can find flight prices for as low as $298. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the evening are often more expensive with an average ticket price of $357.

Cheap New Windsor to Caribbean flight deals and tips

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

Direct flights	None

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

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When did momondo last update prices for flights from New Windsor Stewart Airport to Caribbean?
Prices for flights from New Windsor Stewart Airport to Caribbean refresh daily.
How old do you have to be to fly from New Windsor Stewart Airport to Caribbean?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from New Windsor to Caribbean for you.

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

Yes. momondo enables you to select and highlight flights to Caribbean from New Windsor with this policy.

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

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 from New Windsor.

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

Yes. momondo can track prices for New Windsor to Caribbean 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.