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Cheap flights from New Windsor to Caribbean Islands from $121

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 1/9. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:48 am - 10:59 pmSWF-SJU
10h 11m2 stops
Multiple Airlines Logo
5:00 pm - 10:19 amSJU-SWF
18h 19m1 stop
$328Multiple Airlines
Find Deal
dom., ene. 11 - jue., ene. 15
Multiple Airlines Logo
12:11 pm - 2:50 amSWF-SJU
13h 39m2 stops
Multiple Airlines Logo
3:55 am - 11:08 amSJU-SWF
8h 13m1 stop
$329Multiple Airlines
Find Deal
lun., feb. 2 - mié., feb. 4
Multiple Airlines Logo
11:31 am - 3:00 pmSWF-PUJ
27h 29m1 stop
Multiple Airlines Logo
4:25 pm - 11:11 amPUJ-SWF
19h 46m1 stop
$338Multiple Airlines
Find Deal
vie., oct. 31 - dom., nov. 2
Multiple Airlines Logo
11:09 am - 10:59 pmSWF-SJU
10h 50m1 stop
Multiple Airlines Logo
3:55 am - 11:08 amSJU-SWF
8h 13m1 stop
$349Multiple Airlines
Find Deal
lun., feb. 2 - mié., feb. 4
Multiple Airlines Logo
11:31 am - 11:00 amSWF-MBJ
24h 29m1 stop
Multiple Airlines Logo
1:07 pm - 11:11 amMBJ-SWF
22h 04m1 stop
$351Multiple Airlines
Find Deal
vie., oct. 31 - dom., nov. 2
Multiple Airlines Logo
8:24 pm - 11:37 pmSWF-SJU
26h 13m1 stop
Multiple Airlines Logo
9:37 pm - 10:13 amSJU-SWF
13h 36m1 stop
$354Multiple Airlines
Find Deal
sáb., feb. 21 - jue., feb. 26
Multiple Airlines Logo
11:31 am - 11:28 amSWF-PUJ
23h 57m2 stops
Multiple Airlines Logo
4:25 pm - 11:11 amPUJ-SWF
19h 46m1 stop
$354Multiple Airlines
Find Deal
vie., oct. 31 - dom., nov. 2
Multiple Airlines Logo
11:09 am - 10:59 pmSWF-SJU
10h 50m1 stop
Multiple Airlines Logo
10:59 am - 10:19 amSJU-SWF
24h 20m2 stops
$355Multiple Airlines
Find Deal
lun., feb. 2 - jue., feb. 5
Multiple Airlines Logo
11:09 am - 4:07 pmSWF-SJU
27h 58m2 stops
Multiple Airlines Logo
10:59 am - 10:19 amSJU-SWF
24h 20m2 stops
$375Multiple Airlines
Find Deal
lun., feb. 2 - jue., feb. 5
Multiple Airlines Logo
11:09 am - 10:59 pmSWF-SJU
10h 50m1 stop
Multiple Airlines Logo
2:21 pm - 10:19 amSJU-SWF
20h 58m1 stop
$376Multiple Airlines
Find Deal
lun., feb. 2 - jue., feb. 5

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 octubre 20, 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

dom. 1/11

11:48 am-10:59 pm

2 stops10h 11m

San Juan Luis Munoz Marin Intl

jue. 1/15

5:00 pm-10:19 am

1 stop18h 19m

$328

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 2/2

12:11 pm-2:50 am

2 stops13h 39m

San Juan Luis Munoz Marin Intl

mié. 2/4

3:55 am-11:08 am

1 stop8h 13m

$329

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

vie. 10/31

11:31 am-3:00 pm

1 stop27h 29m

Punta Cana

dom. 11/2

4:25 pm-11:11 am

1 stop19h 46m

$338

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 2/2

11:09 am-10:59 pm

1 stop10h 50m

San Juan Luis Munoz Marin Intl

mié. 2/4

3:55 am-11:08 am

1 stop8h 13m

$349

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

vie. 10/31

11:31 am-11:00 am

1 stop24h 29m

Montego Bay Sangster Intl

dom. 11/2

1:07 pm-11:11 am

1 stop22h 04m

$351

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

sáb. 2/21

8:24 pm-11:37 pm

1 stop26h 13m

San Juan Luis Munoz Marin Intl

jue. 2/26

9:37 pm-10:13 am

1 stop13h 36m

$354

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

vie. 10/31

11:31 am-11:28 am

2 stops23h 57m

Punta Cana

dom. 11/2

4:25 pm-11:11 am

1 stop19h 46m

$354

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 2/2

11:09 am-10:59 pm

1 stop10h 50m

San Juan Luis Munoz Marin Intl

jue. 2/5

10:59 am-10:19 am

2 stops24h 20m

$355

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 2/2

11:09 am-4:07 pm

2 stops27h 58m

San Juan Luis Munoz Marin Intl

jue. 2/5

10:59 am-10:19 am

2 stops24h 20m

$375

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 2/2

11:09 am-10:59 pm

1 stop10h 50m

San Juan Luis Munoz Marin Intl

jue. 2/5

2:21 pm-10:19 am

1 stop20h 58m

$376

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

Direct flights

None
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

  • 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?

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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mié. 11/19
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