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Cheap flights from New Windsor to Caribbean Islands from $131

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Windsor to Caribbean Islands departing on 8/25. 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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Find the cheapest flights from New Windsor to Caribbean Islands

Cheap round-trip flights

Logo
11:01 am - 2:11 pmSWF-SJU
27h 10m3 stops
Logo
2:48 am - 2:11 pmSJU-SWF
11h 23m2 stops
$315
Find Deal
Mon, Oct 20 - Sun, Oct 26
Logo
11:43 am - 2:27 amSWF-BQN
14h 44m1 stop
Logo
3:32 am - 11:03 amBQN-SWF
7h 31m1 stop
$346
Find Deal
Thu, Sep 18 - Sat, Sep 20
Logo
3:01 pm - 11:41 amSWF-PUJ
20h 40m2 stops
Logo
12:36 pm - 10:41 amPUJ-SWF
22h 05m2 stops
$359
Find Deal
Mon, Oct 27 - Thu, Oct 30
Logo
11:43 am - 2:27 amSWF-BQN
14h 44m1 stop
Logo
3:32 am - 11:03 amBQN-SWF
7h 31m1 stop
$365
Find Deal
Thu, Sep 11 - Sat, Sep 13
Logo
5:36 pm - 4:00 pmSWF-SDQ
22h 24m1 stop
Logo
5:05 pm - 4:46 pmSDQ-SWF
23h 41m1 stop
$367
Find Deal
Fri, Aug 22 - Sun, Aug 24
Logo
11:31 am - 11:41 amSWF-PUJ
24h 10m2 stops
Logo
12:36 pm - 10:11 amPUJ-SWF
21h 35m2 stops
$375
Find Deal
Fri, Oct 17 - Sun, Oct 19
Logo
6:18 pm - 2:11 pmSWF-SJU
19h 53m2 stops
Logo
2:48 am - 2:11 pmSJU-SWF
11h 23m2 stops
$380
Find Deal
Mon, Oct 20 - Sun, Oct 26
Logo
5:36 pm - 11:14 amSWF-MBJ
18h 38m1 stop
Logo
10:22 am - 4:46 pmMBJ-SWF
29h 24m1 stop
$387
Find Deal
Fri, Aug 22 - Sun, Aug 24
Logo
5:36 pm - 3:10 pmSWF-SJU
21h 34m2 stops
Logo
4:12 pm - 4:46 pmSJU-SWF
24h 34m2 stops
$388
Find Deal
Fri, Aug 22 - Sun, Aug 24
Logo
5:36 pm - 3:10 pmSWF-SJU
21h 34m2 stops
Logo
4:12 pm - 4:46 pmSJU-SWF
24h 34m2 stops
$389
Find Deal
Fri, Aug 22 - Sun, Aug 24

momondo Fare Finder

 
Customize your flight search to find flights from New Windsor to Caribbean Islands 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 August 12, 2025.
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

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 10/20

11:01 am-2:11 pm

3 stops27h 10m

San Juan Luis Munoz Marin Intl

Sun 10/26

2:48 am-2:11 pm

2 stops11h 23m

$315

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 9/18

11:43 am-2:27 am

1 stop14h 44m

Aguadilla Borinquen

Sat 9/20

3:32 am-11:03 am

1 stop7h 31m

$346

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 10/27

3:01 pm-11:41 am

2 stops20h 40m

Punta Cana

Thu 10/30

12:36 pm-10:41 am

2 stops22h 05m

$359

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 9/11

11:43 am-2:27 am

1 stop14h 44m

Aguadilla Borinquen

Sat 9/13

3:32 am-11:03 am

1 stop7h 31m

$365

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 8/22

5:36 pm-4:00 pm

1 stop22h 24m

Santo Domingo Las Americas

Sun 8/24

5:05 pm-4:46 pm

1 stop23h 41m

$367

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 10/17

11:31 am-11:41 am

2 stops24h 10m

Punta Cana

Sun 10/19

12:36 pm-10:11 am

2 stops21h 35m

$375

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 10/20

6:18 pm-2:11 pm

2 stops19h 53m

San Juan Luis Munoz Marin Intl

Sun 10/26

2:48 am-2:11 pm

2 stops11h 23m

$380

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 8/22

5:36 pm-11:14 am

1 stop18h 38m

Montego Bay Sangster Intl

Sun 8/24

10:22 am-4:46 pm

1 stop29h 24m

$387

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 8/22

5:36 pm-3:10 pm

2 stops21h 34m

San Juan Luis Munoz Marin Intl

Sun 8/24

4:12 pm-4:46 pm

2 stops24h 34m

$388

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 8/22

5:36 pm-3:10 pm

2 stops21h 34m

San Juan Luis Munoz Marin Intl

Sun 8/24

4:12 pm-4:46 pm

2 stops24h 34m

$389

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 Caribbean Islands from

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

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

The cheapest day to depart from New Windsor to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets 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 Islands.

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

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from New Windsor to Caribbean Islands in the afternoon for as low as $298. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the evening because they tend to be around $357. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Best Price Found

$131

Fastest flight time

6h 48m

Direct flights

None

Airports in Caribbean Islands

9 airports
The best one-way flight to Caribbean Islands from New Windsor in the past 72 hours is $131. The best round-trip flight deal from New Windsor to Caribbean Islands found on momondo in the last 72 hours is $315.
The fastest flight from New Windsor to Caribbean Islands takes 6h 48m
There are no direct flights from New Windsor to Caribbean Islands. Popular non-direct routes for this connection are New Windsor Stewart Airport - San Juan Luis Munoz Marin Intl Airport, New Windsor Stewart Airport - Kingston Norman Manley Airport and New Windsor Stewart Airport - Montego Bay Sangster Intl Airport.
There are 9 airports near Caribbean Islands: Kingston Norman Manley (KIN), Santo Domingo Las Americas (SDQ), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), Santiago de los Caballeros (STI), Oranjestad Reina Beatrix (AUA), Aguadilla Borinquen (BQN), San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

  • 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 many operators does momondo search for flights from New Windsor Stewart Airport to Caribbean Islands?

  • 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?

Best airlines flying from New Windsor to Caribbean Islands

Compare and see reviews for airlines that fly from New Windsor to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $90Free CancellationRating
5.8
3,222 reviews
Search Frontier flights
JetBluePriceFrom $244Free CancellationRating
7.2
2,916 reviews
Search JetBlue flights

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.

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