Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Stewart Intl. to Caribbean from $168

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 6/9. 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
0 bags
Thu 6/13
Thu 6/20

Search hundreds of travel sites at once for deals on flights to Caribbean

In the last 7 days travelers have searched 42,566,405 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana3 stops$654
Montego Bay
Montego Bay2 stops$734
Santo Domingo
Santo Domingo1 stop$525
Oranjestad
Oranjestad3 stops$578
Nassau
Nassau1 stop$546
Simpson Bay
Simpson Bay2 stops$593

Good to know

Low season

September

High season

March

Cheapest flight

$168
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from New Windsor 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 to Caribbean from Stewart Intl. 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 to Caribbean with an airline and back to Stewart Intl. 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 to Caribbean from Stewart Intl. up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 6% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
7.6
JetBlueOverall score based on 4483 reviews
8.3Crew
7.8Boarding
7.2Food
7.9Comfort
7.5Entertainment
Airline reviews

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

6.0 GoodOscar, Apr 2024LGA - MCO
Read more about JetBlue reviews

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

I booked this flight using JetBlue points and I was just so happy. The plane was so clean, I had every need met. Thank you!!

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

The staff at JFK were rude and unhelpful. I was harassed for the same bag that I used on my flight to jfk with no issues claiming it was the inappropriate size. The women then allowed my travel companion to board with the same size bag because they thought she was more “humble”. Also on the flight when informing the flight attendant that nationals no longer have to fill out the Bahamas immigration form my statement was met with eye rolling and attitude.

One of the crew members, a male complained about my bag being too heavy, which I felt was really unnecessary. I am disabled and would have carried it myself if I thought it was going to be a problem. In addition the landing was rough because everyone gasped in unison which it touched down.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Surly, unhelpful ground staff at JFK. There was a complete lack of empathy—a flawed check-in ordeal caused us to miss our flight. All airlines that I have ever flown would have worked to help me solve the ticket problem. Instead, frontline employees shrugged their shoulders and pointed fingers at us for having made an error. I will do anything to avoid EVER flying on Jet Blue again. It well deserves its low rank among airlines.

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Arrived 3 hours early and never made it past baggage drop

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Book cheap flights from Stewart Intl. to Caribbean

Recent round-trip flight deals

6/3Mon
1 stop
14h 25mSWF-SJU
6/4Tue
1 stop
16h 24mSJU-SWF
$401
7/20Sat
1 stop
12h 11mSWF-SJU
7/27Sat
1 stop
14h 05mSJU-SWF
$415
6/3Mon
1 stop
14h 25mSWF-SJU
6/5Wed
1 stop
13h 13mSJU-SWF
$433
7/27Sat
1 stop
12h 11mSWF-SJU
8/3Sat
1 stop
14h 05mSJU-SWF
$447
5/17Fri
1 stop
11h 27mSWF-SJU
5/18Sat
2 stops
13h 48mSJU-SWF
$491
5/17Fri
1 stop
11h 27mSWF-SJU
5/18Sat
1 stop
16h 01mSJU-SWF
$503
5/17Fri
1 stop
11h 27mSWF-SJU
5/19Sun
2 stops
19h 45mSJU-SWF
$509
5/17Fri
1 stop
11h 27mSWF-SJU
5/19Sun
2 stops
19h 45mSJU-SWF
$510
5/17Fri
1 stop
14h 25mSWF-SDQ
5/19Sun
2 stops
28h 49mSDQ-SWF
$525
5/19Sun
1 stop
16h 03mSWF-SDQ
5/23Thu
2 stops
20h 20mSDQ-SWF
$531

Search by stops

Search by price

Recent one-way flight deals

6/9Sun
1 stop
14h 57mSWF-SJU
$168
6/9Sun
1 stop
14h 57mSWF-SJU
$169
5/30Thu
2 stops
27h 19mSWF-SXM
$169
5/27Mon
2 stops
13h 42mSWF-SDQ
$194
6/6Thu
2 stops
29h 56mSWF-PUJ
$194
5/27Mon
3 stops
29h 00mSWF-SJU
$197
6/2Sun
2 stops
15h 51mSWF-SDQ
$198
6/6Thu
1 stop
16h 08mSWF-SJU
$200
6/6Thu
2 stops
29h 56mSWF-PUJ
$200
5/17Fri
1 stop
11h 27mSWF-SJU
$206

Search by stops

Search by price

Last minute flights from New Windsor to Caribbean

Last minute flight, train and bus deals

5/17Fri
multi-stop
11h 27mSWF-SJU
5/18Sat
multi-stop
13h 48mSJU-SWF
$491
5/17Fri
multi-stop
11h 27mSWF-SJU
5/18Sat
multi-stop
16h 01mSJU-SWF
$503
5/17Fri
multi-stop
11h 27mSWF-SJU
5/19Sun
multi-stop
19h 45mSJU-SWF
$509
5/17Fri
multi-stop
11h 27mSWF-SJU
5/19Sun
multi-stop
19h 45mSJU-SWF
$510
5/17Fri
multi-stop
14h 25mSWF-SDQ
5/19Sun
multi-stop
28h 49mSDQ-SWF
$525
5/19Sun
multi-stop
16h 03mSWF-SDQ
5/23Thu
multi-stop
20h 20mSDQ-SWF
$531
5/17Fri
multi-stop
14h 25mSWF-SDQ
5/19Sun
multi-stop
27h 56mSDQ-SWF
$541
5/17Fri
multi-stop
14h 23mSWF-SJU
6/22Sat
multi-stop
11h 51mSJU-SWF
$548
5/16Thu
multi-stop
14h 34mSWF-SJU
6/22Sat
multi-stop
11h 51mSJU-SWF
$549
5/16Thu
multi-stop
14h 34mSWF-SJU
5/18Sat
multi-stop
19h 31mSJU-SWF
$590

Search by stops

Search by price