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Find cheap flights from Stewart Intl. to Caribbean Islands from $123

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 Islands departing on 4/5. 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
sam. 4/27
sam. 5/4

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Best Caribbean Islands Flight Deals

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

Montego Bay
Montego Bay2 stops$634
Santo Domingo
Santo Domingo1 stop$362
Oranjestad
Oranjestad3 stops$448
Simpson Bay
Simpson Bay2 stops$430
Aguadilla
Aguadilla1 stop$358

Good to know

Low season

October

High season

April

Cheapest flight

$123
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from New Windsor to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Stewart Intl. to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stewart Intl. to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 airline flying from New Windsor to Caribbean Islands

Need help choosing which airline to fly with from New Windsor to Caribbean Islands? 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 KAYAK reviews.
7.7
JetBlueOverall score based on 4840 reviews
75entertainment
72food
83crew
79comfort
79boarding
77overall
Airline reviews

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!!

Read more about JetBlue

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.

No WiFi No TV Bag of chips I guess it could be worse.

I'll nevere ever give up jet blue for years now and I will never change

From bag drop to boarding, it was great. In-flight is a little different. The seats were a little uncomfortable for that long of a flight. The rest of the cabin crew except for Eva was wonderful. Eva was not friendly at all. I've had to personally encounter her twice in-flight. First time was when I had to go to the lavatory in the back of the plane, and since it was the first for me to board such tiny plane, I didn't know we were using the crew toilet. She was giving me an attitude while telling me where and how to open it since it's not the regular push to open type of door. The second one was when I had to throw trash then use the lavatory again. I asked where to throw them, and unfortunately she was the only crew in the back doodling on her phone, she had to point it out to me with an attitude then told me to wait on the carpet, which I understand because I didn't realize that, but she could have been nicer. After all, I'm a paying customer, and assisting a passenger who isn't knowledgeable about the aircraft is one of the things she's there for. The rest of the experience and crew from bag drop to in-flight were excellent except for her.

Book cheap flights from Stewart Intl. to Caribbean Islands

Recent round-trip flight deals

4/22lun.
3 stops
36h 13mSWF-SJU
5/2jeu.
2 stops
13h 19mSJU-SWF
$287
5/9jeu.
1 stop
7h 43mSWF-BQN
5/12dim.
1 stop
14h 10mBQN-SWF
$358
4/25jeu.
1 stop
14h 56mSWF-SDQ
5/2jeu.
2 stops
20h 27mSDQ-SWF
$362
4/25jeu.
1 stop
14h 56mSWF-SDQ
5/2jeu.
2 stops
20h 27mSDQ-SWF
$363
4/12ven.
2 stops
17h 58mSWF-SDQ
4/15lun.
1 stop
12h 42mSDQ-SWF
$391
6/19mer.
1 stop
13h 15mSWF-SJU
6/22sam.
1 stop
11h 47mSJU-SWF
$423
4/14dim.
2 stops
19h 11mSWF-SXM
4/24mer.
2 stops
19h 06mSXM-SWF
$430
4/21dim.
1 stop
15h 57mSWF-SJU
4/27sam.
1 stop
13h 39mSJU-SWF
$445
4/22lun.
1 stop
15h 30mSWF-SJU
4/28dim.
1 stop
16h 24mSJU-SWF
$459
6/19mer.
1 stop
21h 33mSWF-BQN
6/25mar.
1 stop
15h 36mBQN-SWF
$465

Search by stops

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Recent one-way flight deals

4/5ven.
1 stop
17h 44mSWF-SJU
$123
5/5dim.
1 stop
15h 45mSWF-SJU
$137
4/12ven.
1 stop
21h 11mSWF-SJU
$146
4/5ven.
2 stops
13h 13mSWF-SJU
$153
4/12ven.
2 stops
27h 26mSWF-SJU
$156
4/5ven.
2 stops
13h 13mSWF-SJU
$157
4/19ven.
3 stops
30h 04mSWF-SJU
$158
4/19ven.
2 stops
23h 06mSWF-SJU
$159
4/28dim.
1 stop
15h 15mSWF-BQN
$159
4/15lun.
2 stops
17h 48mSWF-SDQ
$161

Search by stops

Search by price

Last minute flights from New Windsor to Caribbean Islands

Last minute flight, train and bus deals

4/1lun.
multi-stop
27h 48mSWF-SJU
4/11jeu.
multi-stop
31h 06mSJU-SWF
$667
4/1lun.
multi-stop
27h 48mSWF-SJU
4/10mer.
multi-stop
14h 11mSJU-SWF
$670
3/31dim.
multi-stop
15h 16mSWF-BQN
4/6sam.
multi-stop
15h 37mBQN-SWF
$798
4/1lun.
multi-stop
13h 00mSWF-BQN
4/6sam.
multi-stop
15h 37mBQN-SWF
$887
3/29ven.
multi-stop
18h 29mSWF-SDQ
3/31dim.
multi-stop
26h 28mSDQ-SWF
$1,054
3/31dim.
multi-stop
13h 58mSWF-SJU
4/7dim.
multi-stop
28h 06mSJU-SWF
$1,115
4/2mar.
multi-stop
47h 00mSWF-SDQ
4/11jeu.
multi-stop
20h 27mSDQ-SWF
$1,494
4/2mar.
multi-stop
47h 00mSWF-SDQ
4/11jeu.
multi-stop
28h 49mSDQ-SWF
$1,539

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Search by price