$153 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 11/17. 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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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$326
Santo Domingo
Santo Domingo1 stop$393
Montego Bay
Montego Bay1 stop$360
Oranjestad
Oranjestad1 stop$439
Nassau
Nassau1 stop$456
Simpson Bay
Simpson Bay1 stop$1,108
Kingston
Kingston1 stop$394
Aguadilla
Aguadilla1 stop$616
Punta Cana
Punta Cana1 stop$326
Santo Domingo
Santo Domingo1 stop$393
Montego Bay
Montego Bay1 stop$360
Oranjestad
Oranjestad1 stop$439
Nassau
Nassau1 stop$456
Simpson Bay
Simpson Bay1 stop$1,108
Kingston
Kingston1 stop$394
Aguadilla
Aguadilla1 stop$616

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, Oct 6 - Thu, Oct 16
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11:01 am - 2:49 pmSWF-PUJ
27h 48m1 stop
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3:57 pm - 10:41 amPUJ-SWF
18h 44m1 stop
Mon, Oct 6 - Thu, Oct 16
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11:01 am - 10:38 amSWF-STI
23h 37m1 stop
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11:43 am - 10:41 amSTI-SWF
22h 58m1 stop
Mon, Oct 13 - Thu, Oct 23
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11:01 am - 10:38 amSWF-STI
23h 37m1 stop
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11:43 am - 10:41 amSTI-SWF
22h 58m1 stop
Mon, Oct 6 - Sun, Oct 12
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11:01 am - 2:49 pmSWF-PUJ
27h 48m1 stop
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3:57 pm - 10:11 amPUJ-SWF
18h 14m1 stop
Fri, Oct 17 - Thu, Oct 23
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11:31 am - 11:00 amSWF-MBJ
24h 29m1 stop
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12:09 pm - 10:41 amMBJ-SWF
21h 32m1 stop
Fri, Oct 10 - Thu, Oct 23
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11:41 am - 10:38 amSWF-STI
22h 57m1 stop
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11:43 am - 10:41 amSTI-SWF
22h 58m1 stop
Mon, Oct 6 - Sun, Oct 12
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11:01 am - 11:00 amSWF-MBJ
24h 59m1 stop
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12:09 pm - 10:11 amMBJ-SWF
21h 02m1 stop
Fri, Oct 10 - Sun, Oct 19
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11:41 am - 10:38 amSWF-STI
22h 57m1 stop
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11:43 am - 10:11 amSTI-SWF
22h 28m1 stop
Fri, Oct 31 - Sun, Nov 9
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11:31 am - 11:00 amSWF-MBJ
24h 29m1 stop
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1:12 pm - 11:11 amMBJ-SWF
21h 59m1 stop
Fri, Oct 3 - Sun, Oct 5
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12:11 pm - 2:42 pmSWF-SDQ
26h 31m1 stop
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3:54 pm - 10:11 amSDQ-SWF
18h 17m1 stop
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.

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 04m, Kingston, which takes 8h 38m, and San Juan, which takes 10h 22m.

Good to know

Low seasonOctober
Cheapest flight$153
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 37% lower on average.
Flight from Stewart Intl. to Punta Cana

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.
7.2
JetBlueOverall score based on 2918 reviews
7.4Boarding
6.7Food
8.0Crew
7.3Entertainment
7.6Comfort
Airline reviews

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.

2.0 MediocreAnthony, Jul 2025JFK - SAV
Read more JetBlue reviews

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.

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.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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