Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from New Windsor to Caribbean Islands from $114

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 2/22. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
10:29 am - 1:38 am
SWF
-
SDQ
15h 09m
1 stop
Multiple Airlines Logo
2:52 am - 10:55 am
SDQ
-
SWF
8h 03m
1 stop
$364Multiple Airlines
Sun, Apr 5 - Wed, Apr 8
Multiple Airlines Logo
12:11 pm - 11:13 pm
SWF
-
SJU
34h 02m
2 stops
Multiple Airlines Logo
3:36 pm - 9:19 am
SJU
-
SWF
17h 43m
1 stop
$370Multiple Airlines
Fri, Mar 6 - Wed, Mar 11
Multiple Airlines Logo
10:29 am - 1:49 am
SWF
-
STI
15h 20m
1 stop
Multiple Airlines Logo
2:46 am - 10:55 am
STI
-
SWF
8h 09m
1 stop
$370Multiple Airlines
Sun, Apr 5 - Wed, Apr 8
Multiple Airlines Logo
10:00 am - 11:40 pm
SWF
-
SJU
13h 40m
1 stop
Multiple Airlines Logo
7:54 pm - 10:55 am
SJU
-
SWF
15h 01m
1 stop
$374Multiple Airlines
Fri, Apr 3 - Wed, Apr 8
Multiple Airlines Logo
8:40 pm - 10:10 am
SWF
-
SJU
13h 30m
1 stop
Multiple Airlines Logo
7:54 pm - 9:39 am
SJU
-
SWF
13h 45m
1 stop
$376Multiple Airlines
Sun, Mar 22 - Sat, Mar 28
Multiple Airlines Logo
10:09 am - 9:17 am
SWF
-
SJU
23h 08m
2 stops
Multiple Airlines Logo
7:54 pm - 11:39 am
SJU
-
SWF
15h 45m
1 stop
$386Multiple Airlines
Sun, Mar 8 - Sat, Mar 14
Multiple Airlines Logo
11:45 am - 8:44 pm
SWF
-
SJU
8h 59m
1 stop
Multiple Airlines Logo
7:15 am - 6:57 pm
SJU
-
SWF
11h 42m
1 stop
$400Multiple Airlines
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
11:45 am - 4:10 pm
SWF
-
AUA
28h 25m
1 stop
Multiple Airlines Logo
3:41 pm - 10:55 am
AUA
-
SWF
19h 14m
1 stop
$405Multiple Airlines
Thu, Apr 16 - Wed, Apr 22
Multiple Airlines Logo
12:15 pm - 8:47 am
SWF
-
SJU
20h 32m
2 stops
Multiple Airlines Logo
7:05 pm - 8:58 am
SJU
-
SWF
13h 53m
1 stop
$409Multiple Airlines
Fri, May 8 - Sat, May 16
Multiple Airlines Logo
10:29 am - 1:49 am
SWF
-
STI
15h 20m
1 stop
Multiple Airlines Logo
3:43 pm - 11:31 am
STI
-
SWF
19h 48m
2 stops
$433Multiple Airlines
Thu, Mar 19 - Thu, Mar 26

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 February 2, 2026.
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 WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Sun 4/5

10:29 am-1:38 am

1 stop15h 09m

Santo Domingo Las Americas

Wed 4/8

2:52 am-10:55 am

1 stop8h 03m

$364

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 3/6

12:11 pm-11:13 pm

2 stops34h 02m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:36 pm-9:19 am

1 stop17h 43m

$370

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 4/5

10:29 am-1:49 am

1 stop15h 20m

Santiago de los Caballeros

Wed 4/8

2:46 am-10:55 am

1 stop8h 09m

$370

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 4/3

10:00 am-11:40 pm

1 stop13h 40m

San Juan Luis Munoz Marin Intl

Wed 4/8

7:54 pm-10:55 am

1 stop15h 01m

$374

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/22

8:40 pm-10:10 am

1 stop13h 30m

San Juan Luis Munoz Marin Intl

Sat 3/28

7:54 pm-9:39 am

1 stop13h 45m

$376

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/8

10:09 am-9:17 am

2 stops23h 08m

San Juan Luis Munoz Marin Intl

Sat 3/14

7:54 pm-11:39 am

1 stop15h 45m

$386

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 5/7

11:45 am-8:44 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Sun 5/10

7:15 am-6:57 pm

1 stop11h 42m

$400

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Thu 4/16

11:45 am-4:10 pm

1 stop28h 25m

Oranjestad Reina Beatrix

Wed 4/22

3:41 pm-10:55 am

1 stop19h 14m

$405

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 5/8

12:15 pm-8:47 am

2 stops20h 32m

San Juan Luis Munoz Marin Intl

Sat 5/16

7:05 pm-8:58 am

1 stop13h 53m

$409

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 3/19

10:29 am-1:49 am

1 stop15h 20m

Santiago de los Caballeros

Thu 3/26

3:43 pm-11:31 am

2 stops19h 48m

$433

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

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

Fastest flight time

6h 47m

Direct flights

None
The fastest flight from New Windsor to Caribbean Islands takes 6h 47m
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 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
JetBluePriceFrom $227Free CancellationRating
7.2
2,892 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.

An easier way to manage your Caribbean Islands 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 3/4
Wed 3/11
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Londonfrom $323
Flights to Bangkokfrom $509
Flights to Tokyofrom $424
Flights to Los Angelesfrom $46
Flights to Parisfrom $298
Flights to Copenhagenfrom $367
Flights to Istanbulfrom $493
Flights to Manilafrom $498
Flights to Romefrom $346
Flights to Miamifrom $27
Flights to Chicagofrom $46