$114 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 8/11. 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

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Flights Deals

Best Caribbean Flight Deals from New Windsor

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$314
Santo Domingo
Santo Domingo1 stop$349
Montego Bay
Montego Bay1 stop$317
Oranjestad
Oranjestad1 stop$366
Nassau
Nassau1 stop$409
Kingston
Kingston1 stop$374
Simpson Bay
Simpson Bay1 stop$558
Providenciales
Providenciales2 stops$936
Port of Spain
Port of Spain2 stops$763
Punta Cana
Punta Cana1 stop$314
Santo Domingo
Santo Domingo1 stop$349
Montego Bay
Montego Bay1 stop$317
Oranjestad
Oranjestad1 stop$366
Nassau
Nassau1 stop$409
Kingston
Kingston1 stop$374
Simpson Bay
Simpson Bay1 stop$558
Providenciales
Providenciales2 stops$936
Port of Spain
Port of Spain2 stops$763

Cheap Flights from New Windsor to Caribbean

 
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, Jun 23 - Thu, Jun 26
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8:01 pm - 7:19 pmSWF-SJU
23h 18m1 stop
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9:30 am - 7:11 pmSJU-SWF
33h 41m2 stops
Mon, Jun 23 - Thu, Jun 26
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8:01 pm - 7:19 pmSWF-SJU
23h 18m1 stop
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8:24 pm - 7:11 pmSJU-SWF
22h 47m1 stop
Fri, Jul 11 - Thu, Jul 17
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7:56 pm - 1:35 amSWF-SJU
29h 39m2 stops
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10:14 pm - 7:06 pmSJU-SWF
20h 52m1 stop
Mon, Jul 7 - Thu, Jul 10
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7:56 pm - 7:19 pmSWF-SJU
23h 23m1 stop
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10:14 pm - 7:06 pmSJU-SWF
20h 52m1 stop
Mon, Jul 7 - Thu, Jul 10
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7:56 pm - 12:05 amSWF-SJU
28h 09m2 stops
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10:14 pm - 7:06 pmSJU-SWF
20h 52m1 stop
Mon, Jun 23 - Thu, Jun 26
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8:01 pm - 7:19 pmSWF-SJU
23h 18m1 stop
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8:24 pm - 7:11 pmSJU-SWF
22h 47m1 stop
Mon, Jun 23 - Thu, Jun 26
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8:01 pm - 7:19 pmSWF-SJU
23h 18m1 stop
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8:24 pm - 7:11 pmSJU-SWF
22h 47m1 stop
Mon, Jul 14 - Thu, Jul 17
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7:56 pm - 3:30 pmSWF-SJU
19h 34m1 stop
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10:14 pm - 7:06 pmSJU-SWF
20h 52m1 stop
Mon, Jun 30 - Thu, Jul 3
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8:01 pm - 7:19 pmSWF-SJU
23h 18m1 stop
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8:24 pm - 7:06 pmSJU-SWF
22h 42m1 stop
Fri, Jul 11 - Sun, Jul 13
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7:56 pm - 1:35 amSWF-SJU
29h 39m2 stops
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10:14 pm - 7:06 pmSJU-SWF
20h 52m1 stop
Useful Info

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.

How long does a flight from New Windsor to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from New Windsor are to Nassau, which takes 7h 25m, Kingston, which takes 7h 40m, and San Juan, which takes 13h 38m.


Good to know

Low seasonOctober
High seasonFebruary
Cheapest flight$114
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly and prices are also 35% lower on average.
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.

  • 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.

Top airlines 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.
7.3
JetBlueOverall score based on 2925 reviews
6.7Food
7.5Boarding
7.3Entertainment
7.6Comfort
8.0Crew
Airline reviews

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

2.0 MediocreLana, Jun 2025HPN - PBI
Read more JetBlue reviews

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.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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