$108 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 2/22. 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$500
Santo Domingo
Santo Domingo2 stops$705
Montego Bay
Montego Bay1 stop$1,105
Oranjestad
Oranjestad1 stop$624
Nassau
Nassau1 stop$456
Simpson Bay
Simpson Bay1 stop$550
Aguadilla
Aguadilla1 stop$518
Punta Cana
Punta Cana1 stop$500
Santo Domingo
Santo Domingo2 stops$705
Montego Bay
Montego Bay1 stop$1,105
Oranjestad
Oranjestad1 stop$624
Nassau
Nassau1 stop$456
Simpson Bay
Simpson Bay1 stop$550
Aguadilla
Aguadilla1 stop$518

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

Mon, Jan 5 - Fri, Jan 9
Multiple Airlines Logo
11:37 am - 10:05 pm
SWF
-
SJU
9h 28m1 stop
Multiple Airlines Logo
5:18 pm - 5:59 pm
SJU
-
SWF
49h 41m2 stops
$399Multiple Airlines
Sat, Jan 3 - Sat, Jan 10
Multiple Airlines Logo
8:45 pm - 8:58 am
SWF
-
SJU
11h 13m1 stop
Multiple Airlines Logo
9:19 pm - 9:58 am
SJU
-
SWF
13h 39m1 stop
$450Multiple Airlines
Sun, Feb 22 - Wed, Mar 4
Multiple Airlines Logo
11:52 am - 2:45 pm
SWF
-
NAS
26h 53m1 stop
Multiple Airlines Logo
4:00 pm - 9:19 am
NAS
-
SWF
17h 19m1 stop
$456Multiple Airlines
Sun, Feb 22 - Sat, Feb 28
Multiple Airlines Logo
11:52 am - 2:45 pm
SWF
-
NAS
26h 53m1 stop
Multiple Airlines Logo
4:00 pm - 11:02 am
NAS
-
SWF
19h 02m1 stop
$461Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
12:22 pm - 3:31 pm
SWF
-
SJU
26h 09m1 stop
Multiple Airlines Logo
5:20 am - 5:12 pm
SJU
-
SWF
12h 52m2 stops
$462Multiple Airlines
Thu, Feb 19 - Sat, Feb 21
Multiple Airlines Logo
12:22 pm - 3:31 pm
SWF
-
SJU
26h 09m1 stop
Multiple Airlines Logo
3:53 am - 11:08 am
SJU
-
SWF
8h 15m1 stop
$471Multiple Airlines
Mon, Feb 23 - Wed, Mar 4
Multiple Airlines Logo
12:11 pm - 4:25 pm
SWF
-
NAS
28h 14m2 stops
Multiple Airlines Logo
4:00 pm - 9:19 am
NAS
-
SWF
17h 19m1 stop
$484Multiple Airlines
Sat, Jan 3 - Sat, Jan 10
Multiple Airlines Logo
8:45 pm - 2:09 pm
SWF
-
PUJ
16h 24m1 stop
Multiple Airlines Logo
6:49 pm - 9:58 am
PUJ
-
SWF
16h 09m2 stops
$500Multiple Airlines
Sun, Mar 1 - Wed, Mar 4
Multiple Airlines Logo
11:48 am - 11:09 pm
SWF
-
SJU
10h 21m1 stop
Multiple Airlines Logo
8:05 pm - 11:08 am
SJU
-
SWF
16h 03m1 stop
$503Multiple Airlines
Mon, Mar 23 - Sat, Mar 28
Multiple Airlines Logo
9:47 am - 2:45 pm
SWF
-
NAS
28h 58m2 stops
Multiple Airlines Logo
4:00 pm - 9:39 am
NAS
-
SWF
17h 39m1 stop
$509Multiple 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.

Good to know

Cheapest flight$108
Flight from Stewart Intl. to Simpson Bay

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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $298 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $357.

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 2898 reviews
7.2Entertainment
7.4Boarding
6.7Food
8.0Crew
7.6Comfort
Airline reviews

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

4.0 OkayRussell, Sep 2025
HPN - MCO
Read more JetBlue reviews

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.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports