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Cheap flights from Caribbean to New York from $120

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to New York departing on 5/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 am - 9:38 am
SJU
-
SWF
27h 38m
1 stop
Multiple Airlines Logo
10:28 am - 8:48 pm
SWF
-
SJU
10h 20m
1 stop
$330Multiple Airlines
Wed, Jul 1 - Sun, Jul 5
Multiple Airlines Logo
5:15 pm - 9:38 am
SJU
-
SWF
16h 23m
2 stops
Multiple Airlines Logo
10:28 am - 8:48 pm
SWF
-
SJU
10h 20m
1 stop
$362Multiple Airlines
Wed, Jul 1 - Sun, Jul 5
Multiple Airlines Logo
6:05 pm - 8:58 am
SJU
-
SWF
14h 53m
1 stop
Multiple Airlines Logo
10:28 am - 8:48 pm
SWF
-
SJU
10h 20m
1 stop
$429Multiple Airlines
Wed, Jun 24 - Sun, Jun 28
Multiple Airlines Logo
6:16 pm - 8:49 am
SJU
-
SWF
14h 33m
1 stop
Multiple Airlines Logo
10:28 am - 8:48 pm
SWF
-
SJU
10h 20m
1 stop
$434Multiple Airlines
Thu, Jun 18 - Thu, Jun 25
Multiple Airlines Logo
8:00 am - 11:25 am
SJU
-
SWF
27h 25m
1 stop
Multiple Airlines Logo
12:05 pm - 1:54 am
SWF
-
SJU
13h 49m
2 stops
$437Multiple Airlines
Tue, Jul 21 - Sat, Jul 25
Multiple Airlines Logo
2:59 am - 11:08 am
SJU
-
SWF
8h 09m
1 stop
Multiple Airlines Logo
10:28 am - 8:48 pm
SWF
-
SJU
10h 20m
1 stop
$439Multiple Airlines
Mon, Jun 22 - Sun, Jun 28
Multiple Airlines Logo
6:05 pm - 8:58 am
SJU
-
SWF
14h 53m
1 stop
Multiple Airlines Logo
12:05 pm - 12:37 am
SWF
-
SJU
12h 32m
2 stops
$443Multiple Airlines
Wed, Jun 10 - Sat, Jun 20
Multiple Airlines Logo
6:00 am - 9:38 am
SJU
-
SWF
27h 38m
1 stop
Multiple Airlines Logo
12:05 pm - 2:11 am
SWF
-
SJU
14h 06m
2 stops
$456Multiple Airlines
Sat, Aug 1 - Wed, Aug 5
Multiple Airlines Logo
6:00 am - 6:40 pm
SJU
-
SWF
12h 40m
1 stop
Multiple Airlines Logo
12:17 pm - 11:29 pm
SWF
-
SJU
11h 12m
2 stops
$462Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
5:38 pm - 9:38 am
SJU
-
SWF
16h 00m
2 stops
Multiple Airlines Logo
10:28 am - 8:48 pm
SWF
-
SJU
10h 20m
1 stop
$490Multiple Airlines
Wed, Jul 29 - Sun, Aug 2

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to New Windsor that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 23, 2026.
Use the filters below to find and compare flights from Caribbean to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 7/1

6:00 am-9:38 am

1 stop27h 38m

New Windsor Stewart

Sun 7/5

10:28 am-8:48 pm

1 stop10h 20m

$330

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 7/1

5:15 pm-9:38 am

2 stops16h 23m

New Windsor Stewart

Sun 7/5

10:28 am-8:48 pm

1 stop10h 20m

$362

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 6/24

6:05 pm-8:58 am

1 stop14h 53m

New Windsor Stewart

Sun 6/28

10:28 am-8:48 pm

1 stop10h 20m

$429

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 6/18

6:16 pm-8:49 am

1 stop14h 33m

New Windsor Stewart

Thu 6/25

10:28 am-8:48 pm

1 stop10h 20m

$434

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Tue 7/21

8:00 am-11:25 am

1 stop27h 25m

New Windsor Stewart

Sat 7/25

12:05 pm-1:54 am

2 stops13h 49m

$437
Quickest round-trip

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Mon 6/22

2:59 am-11:08 am

1 stop8h 09m

New Windsor Stewart

Sun 6/28

10:28 am-8:48 pm

1 stop10h 20m

$439

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 6/10

6:05 pm-8:58 am

1 stop14h 53m

New Windsor Stewart

Sat 6/20

12:05 pm-12:37 am

2 stops12h 32m

$443

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sat 8/1

6:00 am-9:38 am

1 stop27h 38m

New Windsor Stewart

Wed 8/5

12:05 pm-2:11 am

2 stops14h 06m

$456

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 9/3

6:00 am-6:40 pm

1 stop12h 40m

New Windsor Stewart

Mon 9/7

12:17 pm-11:29 pm

2 stops11h 12m

$462

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 7/29

5:38 pm-9:38 am

2 stops16h 00m

New Windsor Stewart

Sun 8/2

10:28 am-8:48 pm

1 stop10h 20m

$490

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to New York from

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

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

What airlines fly to New Windsor?

JetBlue, Delta and United Airlines are the top three most popular airlines that fly to New Windsor from Caribbean according to our data. JetBlue is the first choice among our users, with 57% of people opting to fly with this airline when traveling to New Windsor. Keep in mind that there are 9 different airlines that fly to New Windsor on a routine basis, so you have a few additional options to choose from.

Cheap Caribbean to New Windsor flight deals and tips

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

Fastest flight time

7h 22m

Direct flights

None
The fastest flight from Caribbean to New Windsor takes 7h 22m
There are no direct flights from Caribbean to New Windsor. There are no popular flight routes from Caribbean to New Windsor.
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Frequently asked questions about flying from Caribbean to New Windsor

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

    Prices for flights from Caribbean to New Windsor Stewart Airport were last updated today.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Caribbean to New Windsor Stewart Airport.

  • What documentation or ID do you need to fly to New Windsor Stewart Airport?

    The necessary travel and health documents for your New Windsor Stewart Airport 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.

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Newburgh
Kingston
Woodstock
Saugerties

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to New Windsor from Caribbean.

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

Flights from Caribbean to New Windsor 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 Caribbean to New Windsor?

momondo helps you find the best flight between Caribbean and New Windsor by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to New Windsor, momondo offers a useful price alert feature which will track prices for flights to New Windsor from Caribbean and alert you when they change.

An easier way to manage your New Windsor trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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