$117 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 8/15. 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$343
Santo Domingo
Santo Domingo1 stop$347
Montego Bay
Montego Bay1 stop$367
Oranjestad
Oranjestad1 stop$440
Nassau
Nassau1 stop$454
Kingston
Kingston1 stop$356
Simpson Bay
Simpson Bay2 stops$711
Providenciales
Providenciales3 stops$1,134
Port of Spain
Port of Spain2 stops$940
Punta Cana
Punta Cana1 stop$343
Santo Domingo
Santo Domingo1 stop$347
Montego Bay
Montego Bay1 stop$367
Oranjestad
Oranjestad1 stop$440
Nassau
Nassau1 stop$454
Kingston
Kingston1 stop$356
Simpson Bay
Simpson Bay2 stops$711
Providenciales
Providenciales3 stops$1,134
Port of Spain
Port of Spain2 stops$940

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

Fri, Aug 15 - Thu, Aug 21
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7:37 pm - 3:10 pmSWF-SJU
19h 33m2 stops
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2:11 am - 4:46 pmSJU-SWF
14h 35m2 stops
Mon, Aug 18 - Thu, Aug 21
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7:37 pm - 1:49 pmSWF-SJU
18h 12m2 stops
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2:11 am - 4:46 pmSJU-SWF
14h 35m2 stops
Mon, Aug 18 - Thu, Aug 21
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7:37 pm - 1:49 pmSWF-SJU
18h 12m2 stops
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2:11 am - 4:46 pmSJU-SWF
14h 35m2 stops
Mon, Aug 11 - Thu, Aug 14
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7:56 pm - 2:45 pmSWF-SJU
18h 49m2 stops
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2:11 am - 6:47 pmSJU-SWF
16h 36m2 stops
Mon, Aug 11 - Thu, Aug 14
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7:56 pm - 2:45 pmSWF-SJU
18h 49m2 stops
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2:11 am - 6:47 pmSJU-SWF
16h 36m2 stops
Fri, Aug 8 - Thu, Aug 14
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7:56 pm - 3:25 pmSWF-SJU
19h 29m2 stops
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2:11 am - 6:47 pmSJU-SWF
16h 36m2 stops
Mon, Aug 4 - Thu, Aug 7
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7:56 pm - 9:50 pmSWF-SJU
25h 54m2 stops
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3:50 pm - 7:06 pmSJU-SWF
27h 16m3 stops
Mon, Aug 4 - Thu, Aug 7
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7:56 pm - 9:50 pmSWF-SJU
25h 54m2 stops
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2:40 am - 7:06 pmSJU-SWF
16h 26m2 stops
Fri, Aug 15 - Thu, Aug 28
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7:37 pm - 3:10 pmSWF-SJU
19h 33m2 stops
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2:11 am - 1:05 pmSJU-SWF
10h 54m2 stops
Fri, Aug 22 - Thu, Aug 28
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5:36 pm - 3:10 pmSWF-SJU
21h 34m2 stops
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2:11 am - 1:05 pmSJU-SWF
10h 54m2 stops
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 38m, Kingston, which takes 8h 18m, and San Juan, which takes 12h 07m.


Good to know

Low seasonOctober
High seasonFebruary
Cheapest flight$117
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.

Reviews of the 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 2913 reviews
7.3Entertainment
8.0Crew
7.6Comfort
6.7Food
7.4Boarding
Airline reviews

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

2.0 MediocreKevin, Jul 2025JFK - POS
Read more JetBlue reviews

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.

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.

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Very bad! No good service delayed my second connection flight

Everything you need to know for your flight to Caribbean

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