$127 Find Cheap Flights from Stewart Intl. 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 8/29. 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$425
Nassau
Nassau2 stops$480
Aguadilla
Aguadilla1 stop$502
Punta Cana
Punta Cana1 stop$425
Nassau
Nassau2 stops$480
Aguadilla
Aguadilla1 stop$502

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

Wed, Aug 26 - Thu, Sep 3
Multiple Airlines Logo
12:05 pm - 12:56 am
SWF
-
SJU
12h 51m
2 stops
Multiple Airlines Logo
6:45 am - 6:40 pm
SJU
-
SWF
11h 55m
1 stop
$256Multiple Airlines
Sat, Aug 29 - Thu, Sep 3
Multiple Airlines Logo
12:05 pm - 12:23 am
SWF
-
SJU
12h 18m
2 stops
Multiple Airlines Logo
6:45 am - 6:40 pm
SJU
-
SWF
11h 55m
1 stop
$263Multiple Airlines
Thu, Aug 27 - Thu, Sep 3
Multiple Airlines Logo
7:31 pm - 4:11 pm
SWF
-
SJU
20h 40m
1 stop
Multiple Airlines Logo
6:45 am - 6:40 pm
SJU
-
SWF
11h 55m
1 stop
$267Multiple Airlines
Sat, Aug 29 - Sun, Aug 30
Multiple Airlines Logo
12:05 pm - 12:56 am
SWF
-
SJU
12h 51m
2 stops
Multiple Airlines Logo
6:45 am - 6:41 pm
SJU
-
SWF
11h 56m
1 stop
$269Multiple Airlines
Wed, Aug 26 - Sun, Aug 30
Multiple Airlines Logo
12:05 pm - 12:56 am
SWF
-
SJU
12h 51m
2 stops
Multiple Airlines Logo
6:45 am - 6:41 pm
SJU
-
SWF
11h 56m
1 stop
$270Multiple Airlines
Sun, Aug 23 - Sun, Aug 30
Multiple Airlines Logo
1:00 pm - 4:11 pm
SWF
-
SJU
27h 11m
1 stop
Multiple Airlines Logo
6:45 am - 6:41 pm
SJU
-
SWF
11h 56m
1 stop
$274Multiple Airlines
Sun, Aug 23 - Thu, Sep 3
Multiple Airlines Logo
1:00 pm - 4:11 pm
SWF
-
SJU
27h 11m
1 stop
Multiple Airlines Logo
6:45 am - 6:40 pm
SJU
-
SWF
11h 55m
1 stop
$277Multiple Airlines
Wed, Aug 26 - Sun, Aug 30
Multiple Airlines Logo
12:05 pm - 12:56 am
SWF
-
SJU
12h 51m
2 stops
Multiple Airlines Logo
6:45 am - 6:41 pm
SJU
-
SWF
11h 56m
1 stop
$281Multiple Airlines
Wed, Aug 19 - Thu, Aug 27
Multiple Airlines Logo
12:05 pm - 12:56 am
SWF
-
SJU
12h 51m
2 stops
Multiple Airlines Logo
6:45 am - 6:41 pm
SJU
-
SWF
11h 56m
1 stop
$282Multiple Airlines
Thu, Aug 6 - Wed, Aug 12
Multiple Airlines Logo
10:28 am - 4:11 pm
SWF
-
SJU
29h 43m
1 stop
Multiple Airlines Logo
6:00 am - 9:38 am
SJU
-
SWF
27h 38m
1 stop
$284Multiple 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 Stewart Intl. 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 Stewart Intl. 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 $227.

Find deals

Good to know

Cheapest flight$127
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.
7.1
JetBlueOverall score based on 3001 reviews
6.6Food
7.2Entertainment
7.5Comfort
7.9Crew
7.3Boarding
Airline reviews

Domestic flights are good. Just stay away from international travel

8.0 ExcellentHugo, Jun 2026
JFK - BUF
Read more JetBlue reviews

Domestic flights are good. Just stay away from international travel

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

Since we started at syr the service, crews, and flights were just excellent

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

Boarding process was terrible. No assigned seat until the gate, then a long line to get seat assignment.

JetBlue was good. Kayak offered us a deal if we bundled the rental car. This was a complete scam. Kayak said the total was $222... but when we went to pick up the car the agent at Rent a wreck said that we had to pay "fees and taxes" for a grand total of $750. I would recommend not using kayak or rent a wreck. They are both complicit in this scam. JetBlue worked out well.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stewart Intl. (SWF)