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Cheap flights from Caribbean to New York from $125

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 8/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Caribbean to New York

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
12:05 pm - 12:56 am
SWF
-
SJU
12h 51m
2 stops
$272Multiple Airlines
Wed, Aug 12 - Wed, Aug 19
Multiple Airlines Logo
6:00 am - 9:38 am
SJU
-
SWF
27h 38m
1 stop
Multiple Airlines Logo
10:28 am - 4:11 pm
SWF
-
SJU
29h 43m
1 stop
$292Multiple Airlines
Sat, Aug 8 - Thu, Aug 13
Multiple Airlines Logo
6:00 am - 9:38 am
SJU
-
SWF
27h 38m
1 stop
Multiple Airlines Logo
10:28 am - 4:11 pm
SWF
-
SJU
29h 43m
1 stop
$294Multiple Airlines
Wed, Aug 5 - Thu, Aug 13
Multiple Airlines Logo
6:00 am - 9:38 am
SJU
-
SWF
27h 38m
1 stop
Multiple Airlines Logo
10:28 am - 4:11 pm
SWF
-
SJU
29h 43m
1 stop
$317Multiple Airlines
Sat, Aug 1 - Thu, Aug 6
Multiple Airlines Logo
10:19 am - 9:38 am
SDQ
-
SWF
23h 19m
1 stop
Multiple Airlines Logo
10:28 am - 11:12 pm
SWF
-
SDQ
12h 44m
1 stop
$512Multiple Airlines
Wed, Jul 29 - Thu, Aug 13
Multiple Airlines Logo
10:48 pm - 5:54 pm
SJU
-
SWF
19h 06m
1 stop
Multiple Airlines Logo
10:33 am - 7:32 pm
SWF
-
SJU
8h 59m
1 stop
$514Multiple Airlines
Fri, Jul 24 - Sun, Jul 26
Multiple Airlines Logo
10:19 am - 9:38 am
SDQ
-
SWF
23h 19m
1 stop
Multiple Airlines Logo
10:28 am - 11:12 pm
SWF
-
SDQ
12h 44m
1 stop
$520Multiple Airlines
Wed, Jul 15 - Thu, Jul 30
Multiple Airlines Logo
3:35 pm - 9:38 am
SDQ
-
SWF
18h 03m
1 stop
Multiple Airlines Logo
7:31 pm - 4:29 pm
SWF
-
SDQ
20h 58m
1 stop
$522Multiple Airlines
Sat, Aug 15 - Sun, Aug 30
Multiple Airlines Logo
10:48 pm - 11:08 am
SJU
-
SWF
12h 20m
1 stop
Multiple Airlines Logo
12:17 pm - 2:15 am
SWF
-
SJU
13h 58m
2 stops
$618Multiple Airlines
Mon, Aug 10 - Mon, Aug 17
Multiple Airlines Logo
10:48 pm - 11:37 am
SJU
-
SWF
12h 49m
2 stops
Multiple Airlines Logo
12:17 pm - 2:15 am
SWF
-
SJU
13h 58m
2 stops
$624Multiple Airlines
Thu, Aug 13 - Mon, Aug 17

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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 June 22, 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 8/12

6:00 am-9:38 am

1 stop27h 38m

New Windsor Stewart

Wed 8/19

12:05 pm-12:56 am

2 stops12h 51m

$272

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sat 8/8

6:00 am-9:38 am

1 stop27h 38m

New Windsor Stewart

Thu 8/13

10:28 am-4:11 pm

1 stop29h 43m

$292

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 8/5

6:00 am-9:38 am

1 stop27h 38m

New Windsor Stewart

Thu 8/13

10:28 am-4:11 pm

1 stop29h 43m

$294

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

Thu 8/6

10:28 am-4:11 pm

1 stop29h 43m

$317

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Wed 7/29

10:19 am-9:38 am

1 stop23h 19m

New Windsor Stewart

Thu 8/13

10:28 am-11:12 pm

1 stop12h 44m

$512

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Fri 7/24

10:48 pm-5:54 pm

1 stop19h 06m

New Windsor Stewart

Sun 7/26

10:33 am-7:32 pm

1 stop8h 59m

$514

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Wed 7/15

10:19 am-9:38 am

1 stop23h 19m

New Windsor Stewart

Thu 7/30

10:28 am-11:12 pm

1 stop12h 44m

$520

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Sat 8/15

3:35 pm-9:38 am

1 stop18h 03m

New Windsor Stewart

Sun 8/30

7:31 pm-4:29 pm

1 stop20h 58m

$522
Quickest round-trip

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Mon 8/10

10:48 pm-11:08 am

1 stop12h 20m

New Windsor Stewart

Mon 8/17

12:17 pm-2:15 am

2 stops13h 58m

$618

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 8/13

10:48 pm-11:37 am

2 stops12h 49m

New Windsor Stewart

Mon 8/17

12:17 pm-2:15 am

2 stops13h 58m

$624

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 8 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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