$134 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 2/26. 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$393
Santo Domingo
Santo Domingo2 stops$952
Montego Bay
Montego Bay1 stop$539
Oranjestad
Oranjestad1 stop$394
Nassau
Nassau1 stop$572
Aguadilla
Aguadilla1 stop$388
Punta Cana
Punta Cana1 stop$393
Santo Domingo
Santo Domingo2 stops$952
Montego Bay
Montego Bay1 stop$539
Oranjestad
Oranjestad1 stop$394
Nassau
Nassau1 stop$572
Aguadilla
Aguadilla1 stop$388

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 29 - Mon, Feb 2
Multiple Airlines Logo
12:13 pm - 11:33 pm
SWF
-
SJU
10h 20m
1 stop
Multiple Airlines Logo
6:00 am - 6:43 pm
SJU
-
SWF
13h 43m
1 stop
$379Multiple Airlines
Mon, May 25 - Sat, May 30
Multiple Airlines Logo
9:41 am - 8:47 am
SWF
-
SJU
23h 06m
1 stop
Multiple Airlines Logo
7:05 pm - 8:58 am
SJU
-
SWF
13h 53m
1 stop
$380Multiple Airlines
Thu, Mar 19 - Wed, Mar 25
Multiple Airlines Logo
11:48 am - 1:42 am
SWF
-
BQN
13h 54m
1 stop
Multiple Airlines Logo
2:42 am - 11:08 am
BQN
-
SWF
8h 26m
1 stop
$388Multiple Airlines
Fri, Mar 6 - Sun, Mar 8
Multiple Airlines Logo
11:02 am - 8:25 pm
SWF
-
PUJ
8h 23m
1 stop
Multiple Airlines Logo
11:35 am - 10:12 am
PUJ
-
SWF
22h 37m
1 stop
$393Multiple Airlines
Sun, Apr 12 - Sun, Apr 19
Multiple Airlines Logo
11:45 am - 2:26 pm
SWF
-
AUA
26h 41m
1 stop
Multiple Airlines Logo
3:41 pm - 10:55 am
AUA
-
SWF
19h 14m
2 stops
$394Multiple Airlines
Sun, Mar 15 - Sat, Mar 21
Multiple Airlines Logo
12:29 pm - 8:53 am
SWF
-
SJU
20h 24m
2 stops
Multiple Airlines Logo
7:54 pm - 9:39 am
SJU
-
SWF
13h 45m
1 stop
$400Multiple Airlines
Thu, Apr 2 - Wed, Apr 8
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
$410Multiple Airlines
Sun, Apr 12 - Sun, Apr 19
Multiple Airlines Logo
11:45 am - 2:26 pm
SWF
-
AUA
26h 41m
1 stop
Multiple Airlines Logo
3:41 pm - 10:55 am
AUA
-
SWF
19h 14m
2 stops
$411Multiple Airlines
Sun, Mar 15 - Sat, Mar 21
Multiple Airlines Logo
11:48 am - 8:53 am
SWF
-
SJU
21h 05m
1 stop
Multiple Airlines Logo
7:54 pm - 9:39 am
SJU
-
SWF
13h 45m
1 stop
$418Multiple Airlines
Thu, Mar 19 - Wed, Mar 25
Multiple Airlines Logo
11:48 am - 1:42 am
SWF
-
BQN
13h 54m
1 stop
Multiple Airlines Logo
2:42 am - 11:08 am
BQN
-
SWF
8h 26m
1 stop
$431Multiple 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$134
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.

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 2888 reviews
7.2Entertainment
8.0Crew
7.5Comfort
6.6Food
7.4Boarding
Airline reviews

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

2.0 MediocreG, Jan 2026
JFK - PVD
Read more JetBlue reviews

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stewart Intl. (SWF)