$119 Find Cheap Flights from New Windsor to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Caribbean departing on 1/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from New Windsor to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$396
Santo Domingo
Santo Domingo1 stop$542
Montego Bay
Montego Bay1 stop$448
Oranjestad
Oranjestad1 stop$389
Nassau
Nassau1 stop$461
Aguadilla
Aguadilla1 stop$342
Punta Cana
Punta Cana1 stop$396
Santo Domingo
Santo Domingo1 stop$542
Montego Bay
Montego Bay1 stop$448
Oranjestad
Oranjestad1 stop$389
Nassau
Nassau1 stop$461
Aguadilla
Aguadilla1 stop$342

Book Cheap New Windsor to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Windsor to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Windsor to Caribbean

Thu, Jan 22 - Wed, Jan 28
Multiple Airlines Logo
12:13 pm - 11:59 pm
SWF
-
SJU
10h 46m1 stop
Multiple Airlines Logo
7:00 pm - 10:19 am
SJU
-
SWF
40h 19m2 stops
$296Multiple Airlines
Sun, Mar 22 - Sat, Mar 28
Multiple Airlines Logo
8:40 pm - 12:59 pm
SWF
-
SJU
16h 19m1 stop
Multiple Airlines Logo
3:22 pm - 9:39 am
SJU
-
SWF
18h 17m1 stop
$297Multiple Airlines
Thu, Jan 22 - Thu, Jan 29
Multiple Airlines Logo
12:13 pm - 11:59 pm
SWF
-
SJU
10h 46m1 stop
Multiple Airlines Logo
4:40 pm - 10:19 am
SJU
-
SWF
18h 39m1 stop
$327Multiple Airlines
Thu, Feb 19 - Wed, Feb 25
Multiple Airlines Logo
11:48 am - 2:57 am
SWF
-
BQN
14h 09m1 stop
Multiple Airlines Logo
3:58 am - 11:08 am
BQN
-
SWF
8h 10m1 stop
$342Multiple Airlines
Thu, Jan 8 - Sat, Jan 10
Multiple Airlines Logo
12:13 pm - 2:48 am
SWF
-
BQN
13h 35m1 stop
Multiple Airlines Logo
3:43 am - 11:33 am
BQN
-
SWF
8h 50m1 stop
$353Multiple Airlines
Fri, Feb 20 - Sat, Feb 21
Multiple Airlines Logo
12:11 pm - 2:57 am
SWF
-
BQN
13h 46m2 stops
Multiple Airlines Logo
3:58 am - 11:08 am
BQN
-
SWF
8h 10m1 stop
$381Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
Multiple Airlines Logo
11:09 am - 3:35 pm
SWF
-
AUA
27h 26m1 stop
Multiple Airlines Logo
4:50 pm - 10:19 am
AUA
-
SWF
18h 29m1 stop
$389Multiple Airlines
Fri, Mar 6 - Sun, Mar 8
Multiple Airlines Logo
11:02 am - 8:25 pm
SWF
-
PUJ
8h 23m1 stop
Multiple Airlines Logo
11:35 am - 10:12 am
PUJ
-
SWF
22h 37m1 stop
$396Multiple Airlines
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
11:09 am - 4:36 pm
SWF
-
PUJ
28h 27m1 stop
Multiple Airlines Logo
5:47 pm - 9:58 am
PUJ
-
SWF
41h 11m2 stops
$416Multiple Airlines
Mon, Feb 9 - Sat, Feb 21
Multiple Airlines Logo
7:33 pm - 2:57 am
SWF
-
BQN
30h 24m1 stop
Multiple Airlines Logo
3:58 am - 11:08 am
BQN
-
SWF
8h 10m1 stop
$427Multiple Airlines
Booking Insights

KAYAK's insights & trends for New Windsor to Caribbean flights

Get data-powered insights and trends into flights from New Windsor to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between New Windsor and Caribbean?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from New Windsor to Caribbean.

There is just one airline that flies from New Windsor to Caribbean direct and that is JetBlue. The best round-trip deal found from JetBlue for the route is to San Juan Luis Munoz Marin Intl Airport (SJU) and costs $244.

Find deals

Good to know

Cheapest flight$130
Flight from Stewart Intl. to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Stewart Intl. to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Stewart Intl. to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stewart Intl. to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Stewart Intl. to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Stewart Intl. to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Stewart Intl. to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Stewart Intl. to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Stewart Intl. to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from New Windsor to Caribbean

 
Need help choosing which airline to fly with from New Windsor to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
JetBlueOverall score based on 2901 reviews
7.4Boarding
7.5Comfort
6.7Food
7.2Entertainment
8.0Crew
Airline reviews

Not a pleasant experience, service was poor. Didn't like it

4.0 OkayMarianna, Dec 2025
JFK - GYE
Read more JetBlue reviews

Not a pleasant experience, service was poor. Didn't like it

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stewart Intl. (SWF)