Find cheap flights from Stewart Intl. to Caribbean

Search hundreds of travel sites at once for deals on flights to Caribbean. Bundle your flight + hotel and save!

SWF — Caribbean
Sep 23 — Sep 301
Round-trip
1 adult
Economy
0 bags
From?
To?
Thu 9/23
Thu 9/30

Good to know

Low season

JanuaryBest time to beat the crowds with an average 7% drop in price.

High season

DecemberMost popular time to fly with an average 7% increase in price.

Average price round-trip

$511(avg. price over the last 2 weeks)

Good deal round-trip

$225or less

Good deal one-way

$168or less

Top tips for finding cheap flights to Caribbean

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean is August.
  • Morning departure is around 1,394% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean flights

  • The cheapest ticket to Caribbean from Stewart Intl. found in the last 72 hours was $100 one-way, and $134 round-trip. The most popular route is from New Windsor Stewart to San Juan Luis Munoz Marin Intl, and the cheapest round-trip airline ticket found on this route in the last 72 hours was $64.

  • 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.

  • 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.

  • 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.

  • 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.

Top airlines flying New Windsor Stewart to Caribbean

Scores according to KAYAK customer reviews
7.2
American AirlinesOverall score based on 46313 reviews
7.5Boarding
7.1Comfort
7.8Crew
6.8Entertainment
6.7Food


Pros: Excellent service.

Pros: On time

Pros: Landing
Cons: Everything. Major delays lost vacation times

Pros: Everything
Cons: No comments

Pros: The price.
Cons: Flight was delayed for 2 hours in Airbus 777 full of passengers. The reason was to fix some light and administrative error on a log book. This could have been prevented if they had done all of the checks beforehand. All of those passengers stuck in a plane during a pandemic. Not very smart !!!!

Pros: On time take off and the fact that we arrived alive.
Cons: Hot meals and inflight entertainment. No even drinks were served.

Pros: Great service and comfortable; well sanitized.
Cons: TV screens for movies and shows.

Cons: Some of the crew had an attitude and the purchased WiFi did not work

Cons: Almost 4 hour delay.

Cons: Ability to download premade events apple calendar and apple wallet tickets was seemingly impossible. Send me one email with each of those items as it’s one of the number one thing customers care about

Pros: Crew helped us find new seats on board.
Cons: American Airlines changed our seats after ticket purchase so that we were not sitting together. We chose seats at check-in in San Francisco so that we could sit together. When we landed in Miami we discovered our seats had been changed yet again and we were seated in different rows, middle seat!

Pros: Smooth ride

Cons: Feeling of being cramped

Pros: Crew was great!

Cons: Todo bien

Pros: Service from crew was fine
Cons: No delay! Got notification that our flight was one half hour earlier. Then boarded aircraft, and it had electrical problems. Delayed. We had to get off. Then board another aircraft.

Pros: Checking in with my Mum who needs assistance was excellent.
Cons: Lack of Entertainment.

Pros: Time of flight
Cons: Aircraft had no screen, old, uncomfortable

Pros: That I could watch movies
Cons: How complicated it was to watch movies. Look at Netflix, they know how to do it right.

Pros: Movie options were good.
Cons: The a/c was not working well and t

Pros: Reliability that your flight will not be cancelled. Punctuality.
Cons: They charge you $125 for a dog in cabin (JetBlue and Southwest near $100, Frontier $75). There is NO benefit, even with this extra amount of money. I was assigned to enter the aircraft in Group 8... I suggest AA the benefit to enter (at least) in Group 5 for people with PAID in cabin dogs.

Pros: Service
Cons: Seats and space

Pros: The only good thing about this flight was the free plastic cup of water they gave us right before we landed. Thanks!
Cons: The stewardess was outright mean! I am disabled and showed up in a wheelchair. The woman had the nerve to ask me if I was really disabled or if I was using it to cut the line. It was really horrible!

Pros: Turkey sandwich snd boarding went smoothly
Cons: There was no entertainment and since there is no WiFi for most of the flight due to being over water the flight seemed longer than what it actually was.

Cons: Dallas to San Juan San Juan Dallas American Airlines has the worst seat of any airline flown by us fare almost 2000 dollars for round trip and the seat is small hard uncomfortable even for a short flight this is no business class!!

Cons: Last minute cancellation and reschedule if original flight with 20 people hounding the gate for standby status. Craziness. These last minute revisions mist stop

Pros: USB Outlets are nice to have
Cons: Nothing was bad on this flight

Pros: Schedule was punctual. The entertainment was superb. Good crew. The overhead bins were, for some reason, larger which aided the boarding process.
Cons: I guess the lack of snack options but that is just the way it is nowadays.

Pros: Can't think of anything good
Cons: SEE: Customer Relations request #1-249830721

Pros: Nice crew clean airplane
Cons: Initial flight was cancelled after 2 hours delay. My next flight was scheduled the earliest possible by AA which was 24 hours later. No transportation,hotel or miles compensation for this. I had work and responsabilities the next day. TThe scheduled trip was supposed to take off at 7:45. Boarding started late and was very slow. My bag fit the meassurements and still was forced to check it (which I did not want to do as I did not want to be waiting an hour for my bag at my arrival as I had work early the next day. In addition there was airplaine traffic as it was "rush hour" instead of flying at 7:45 we departed almost at 9pm!!!! Have to pay for food Quality of tv monitors very poor And in an uncomfortable position No movie options No wifi although stated the aircraft has Non functioning electrical plug

Pros: Nothing
Cons: Never made it to San Juan to catch my cruise. To top things off I was a ship for two days without my luggage and underwears. Never again!!! Thank you JetBlue!!!

Pros: The pilot was a riot, the flight was on time. Again, nothing wrong, nothing special. As it should be (if only we had more leg and seat room, and I am pretty streamline).

Pros: Nothing
Cons: Super old planes, no had a tv.

Pros: Puntuality

Pros: Crew was good.
Cons: The television was in the aisle and couldn't be properly seen. Also there was no outlet charger. During boarding, even thou they called by group number, the crew allowed a queue in the front, making it confusing who was in line and who wasn't. Better wait till the end to board that get in that mess

Cons: There seets are two small. And they dont sell alcohol. That sucks.

Cons: The airline had trouble with the plane. After we waited 3 hrs in the plane they cancel the flight. They offer a hotel but it was very dirty

Pros: Nothing. My fight from San Juan to Miami on Friday Oct. 7 was cancelled because of hurricane Matthews, since I didnot buy a roundtrip with AA they did not reimburse or offer me a credit for my returning flight. I contacted AA in two ocassions and both times their personnel were impersonal and even rude to me with the whole situation. I ended up losing $250 because of choosing American Airlines. I will do my best to avoid traveling with American ever again, and I will spread the word, as well. I felt robbed, so unfair.
Cons: Everything

Pros: Friendly polite staff. Plane left and arrived on time.

Cons: No have owned screen TV

Pros: Even when the plane was full they managed to help passengers to get seated.
Cons: If you still flying economy class, why would you have to pay extra for exit row where the seats are the same. Only received pretzel and a cup of drink on a 3 hour flight once.

Pros: Everything
Cons: Nothing

Pros: Comfortable seat
Cons: Lack of entertainment

Cons: One hour delay sitting inside the plane with no pilot!! And to top it off, the air conditioner was off!! Will never fly American ever again.

Cons: Terrible airport assistance, many unnecessary customs checks, uncomfortable seats, on flight bad service and late flight times.

Cons: Gg

Pros: I live the service which make me feel good. Also the flight was very quiet and the crew help me in everything I asked.

Pros: The great atendance and on time bording
Cons: There is no More options of free food included with the ticket fly and it was a longer flight and there wasn't no tv, no entertament

Pros: My window seat was all.
Cons: I didn't get a call about the delay like other passengers, only an email at 7am as I was in line to check in for the 8:25am flight 395. The female crew members, a dark haired woman and a short blond haired woman both would have ignored me if the other two people seated by me did not also try to get their attention. The dark haired woman gave the guy next to me headphones and when I held out my hand she just looked at me and walked away as if she'd been called away. Which she hadn't she came back and started with the row immediately behind us and the guy next to me was nice enough to give me his. Also after nearly waiting 4 hours, 9 minutes before boarding we were given food vouchers and told to "run and hurry" and get food "to go" so most people didn't even bother using the vouchers because of that. I've had better flights with American Airlines, I just didn't know this one would be so poor. Definitely way below average expectations.

Cons: Exelente

Cons: More Comfortable seats

Cons: Everything

Pros: It was ok, one gets what one pays and I understand that.
Cons: Some padding on the chairs would have been welcome.

Pros: Check in was

Pros: Nothing
Cons: Smoother ride to location

Cons: Nothing because everything is good.

Pros: En realidad nada porque desde los empleados hasta las azafatas del avión brindan muy pésimo servicio
Cons: Todo Check in Empleados Meriendas Entretenimiento

Cons: Frontier is usually good, not this flight. Dirty and packed full, not clean at all.

Cons: Covid prevention methods need to be fixed ASAP, I don't trust Frontier with my health safety. Everyone was cramped in the plane and there was not any space betweem seats like other airlines. The app did not work to pay for carryon and I had to pay $60 in the front desk.

Pros: That was fun
Cons: The food in the airplane

Pros: The crew of the flight was good but the seat are no comfortable.
Cons: Comfortable seats.

Pros: Everything was perfect flight on time the baggage very fast and the flight was just 3:30 minutes smoother than u can ask!

Pros: Once again everyone was so wonderful and helpful
Cons: Lower luggage cost. I spent $110 additional on this trip since since I wasn't well informed (my fault)

Pros: Nothing
Cons: Everything

Pros: Nothing
Cons: Staff crabage

Pros: Fast easy boarding, friendly helpful staff
Cons: There was more kids sitting on their parents lap than I’ve ever seen before and it made a very chaotic noisy flight

Pros: The crew was great, the chairs are uncomfortable.
Cons: For the price it’s great.

Cons: For the price, you cannot go wrong. Would recommend and travel again with this airline.

Cons: People should be restrained from jamming entrance to aircraft BEFORE their zone is called.

Cons: Never happened, the flight was cancelled and never rebooked.

Cons: The flight was delayed, it was a mess.

Cons: Boarding

Pros: Great flught for the price.
Cons: Can’t complain.

Cons: Good

Cons: Tremenda porquería horrendo

Pros: Crew was amazing, I love that they had tablets to take the order instead of driving the cart up and down the aisle.
Cons: Paid fifty dollars for more leg room and it basically felt like basic seats that I’ve flown with such as spirit and American Airlines

Pros: Yes
Cons: Food

Cons: Everything was good. It’s was a nice travel... safety and puntual. I like that... the only things I think they may could be better is the airplane seat. And they don’t have television.

Pros: Me cobraron por bulto de mano lo que lo encuentro inlógico porque con ese bulto viaje a Philadelphia y al volver me vienen a cobrar $60 no tiene sentido
Cons: Como comenté anterior Me cobraron por bulto de mano lo que lo encuentro inlógico porque con ese bulto viaje a Philadelphia y al volver me vienen a cobrar $60 no tiene sentido deben mejorar y no cojer a la gente de boba eso no se hace primera y última vez que viajo por Frontier

Pros: On time, new comfortable plane.
Cons: Entertainment?

Pros: No issues

Pros: Price
Cons: Hardest most uncomfortable seats, ever!

Pros: Nice, New plane. Pilot made up lost time in the air.
Cons: Ridiculous baggage charges. Only pay food. No internet. No screens.

Pros: SEAT was comfortable
Cons: Service

Pros: Price on the flight to ket
Cons: Sits are really uncomfortable, staff wasn't courteous and boarding process was a mess

Pros: Estaba todo bien.
Cons: Pero no me gusto q havia mucha turbulencia. Y mis photos queria esplotar.

Cons: The crew were not welcoming or friendly. One of them (blond, curly hair) was mean and disrespectful to everyone. She had an attitude all the time. Just the opposite of my flight from SJU to ATL. Other than that, the flight was on time, etc.

Pros: Good

Pros: We had an uneventful flight
Cons: Didn’t depart until 1055 pm. One hour later than scheduled

Cons: Las 2 horas de retraso del vuelo.

Cons: The seats are very uncomfortable

Pros: Everything went well. No issues at all.
Cons: Deplaning is slow. Should consider a rear deplaning procedure from back doors into tarmac and into terminal.

Pros: Nice service. Exceptionally new plane about a year old to the month.
Cons: Need to ask people to prepare to deplane. Perhaps use rear door to expedite process

Pros: Great service.
Cons: Limited food

Pros: The flight was Very puntual, clean and nice personal in the round trip. I will recomend to my friends and I will flight again soon.
Cons: Nothing

Pros: El personal muy atento
Cons: Asientos un poco incómodos, no hay entretenimiento

Pros: On time, attentive service
Cons: Food selection limited

Pros: No setbacks. On time departures. Arrival ahead of time.
Cons: Food is quite limited.

Pros: boarding and treatment by staff wad excellent
Cons: $3 for a cup of coffee is outrageous.... other airlines at least include beverages and a snack (peanuts etc).

COVID-19 information

Safety measures for airlines flying from Stewart Intl. to Caribbean

Airlines flying from Stewart Intl. to Caribbean have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Stewart Intl. to Caribbean

Mandatory masks

Masks required on board, masks provided on flights from Stewart Intl. to Caribbean

Social distancing seating

Middle seats unavailable to book on flights from Stewart Intl. to Caribbean

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Stewart Intl. to Caribbean

Flexible cancellations

Waiving of change fees. Search flexible flights from Stewart Intl. to Caribbean

Book cheap flights from Stewart Intl. to Caribbean

Recent round-trip flight deals

11/14Sun
1 stopMultiple Airlines
11h 18mSWF-SJU
11/17Wed
1 stopMultiple Airlines
9h 37mSJU-SWF
$134
11/7Sun
1 stopMultiple Airlines
11h 18mSWF-SJU
11/10Wed
1 stopMultiple Airlines
10h 03mSJU-SWF
$136
10/29Fri
1 stopMultiple Airlines
9h 27mSWF-SJU
11/6Sat
1 stopMultiple Airlines
11h 22mSJU-SWF
$157
11/2Tue
2 stopsMultiple Airlines
12h 23mSWF-SJU
11/7Sun
1 stopMultiple Airlines
12h 06mSJU-SWF
$166
11/2Tue
2 stopsMultiple Airlines
12h 23mSWF-SJU
11/6Sat
1 stopMultiple Airlines
10h 03mSJU-SWF
$171
12/2Thu
1 stopMultiple Airlines
9h 54mSWF-SJU
12/7Tue
1 stopMultiple Airlines
13h 10mSJU-SWF
$176
10/29Fri
1 stopMultiple Airlines
9h 40mSWF-SJU
11/1Mon
1 stopMultiple Airlines
11h 42mSJU-SWF
$177
10/29Fri
1 stopMultiple Airlines
9h 40mSWF-SJU
11/7Sun
1 stopMultiple Airlines
12h 06mSJU-SWF
$178
12/3Fri
1 stopMultiple Airlines
12h 22mSWF-SJU
12/4Sat
1 stopMultiple Airlines
9h 05mSJU-SWF
$189
12/2Thu
1 stopMultiple Airlines
9h 54mSWF-SJU
12/6Mon
1 stopMultiple Airlines
9h 05mSJU-SWF
$194
12/2Thu
1 stopMultiple Airlines
9h 54mSWF-SJU
12/4Sat
1 stopMultiple Airlines
9h 05mSJU-SWF
$197
11/4Thu
1 stopMultiple Airlines
11h 13mSWF-SJU
11/6Sat
1 stopMultiple Airlines
10h 03mSJU-SWF
$202
11/6Sat
1 stopFrontier
7h 19mSWF-SJU
11/7Sun
1 stopFrontier
6h 50mSJU-SWF
$248
10/29Fri
1 stopFrontier
9h 40mSWF-SJU
11/1Mon
1 stopFrontier
7h 09mSJU-SWF
$258
1/4Tue
1 stopFrontier
11h 15mSWF-SJU
1/11Tue
1 stopFrontier
21h 05mSJU-SWF
$280
11/7Sun
1 stopFrontier
11h 18mSWF-SJU
11/9Tue
1 stopFrontier
6h 50mSJU-SWF
$296
11/9Tue
1 stopFrontier
19h 13mSWF-PUJ
11/16Tue
1 stopFrontier
18h 31mPUJ-SWF
$303
11/4Thu
1 stopFrontier
20h 46mSWF-PUJ
11/10Wed
1 stopFrontier
27h 02mPUJ-SWF
$305
11/6Sat
1 stopFrontier
20h 19mSWF-PUJ
11/13Sat
1 stopFrontier
27h 02mPUJ-SWF
$312
11/5Fri
1 stopFrontier
27h 33mSWF-SDQ
11/9Tue
1 stopFrontier
18h 04mSDQ-SWF
$313

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Recent one-way flight deals

11/14Sun
1 stopFrontier
11h 18mSWF-SJU
$64
11/16Tue
1 stopFrontier
11h 17mSWF-SJU
$65
11/10Wed
1 stopFrontier
28h 57mSWF-NAS
$74
11/18Thu
1 stopMultiple Airlines
11h 40mSWF-SJU
$86
12/10Fri
1 stopFrontier
15h 34mSWF-SJU
$88
11/9Tue
1 stopFrontier
11h 17mSWF-SJU
$89
12/9Thu
1 stopMultiple Airlines
9h 54mSWF-SJU
$96
12/5Sun
1 stopMultiple Airlines
9h 54mSWF-SJU
$98
10/29Fri
1 stopFrontier
9h 40mSWF-SJU
$100
9/30Thu
2 stopsAmerican Airlines
16h 50mSWF-SJU
$101
11/9Tue
1 stopMultiple Airlines
23h 26mSWF-NAS
$103
11/19Fri
1 stopMultiple Airlines
13h 24mSWF-SJU
$108
9/30Thu
2 stopsAmerican Airlines
16h 50mSWF-SJU
$116
11/10Wed
2 stopsMultiple Airlines
24h 44mSWF-NAS
$117
12/14Tue
1 stopFrontier
11h 15mSWF-SJU
$118
1/11Tue
1 stopMultiple Airlines
10h 18mSWF-SJU
$123
12/12Sun
1 stopFrontier
19h 05mSWF-PUJ
$123
2/15Tue
1 stopMultiple Airlines
10h 18mSWF-SJU
$125
9/30Thu
2 stopsAmerican Airlines
16h 50mSWF-SJU
$146
9/27Mon
2 stopsAmerican Airlines
17h 59mSWF-NAS
$166

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Stewart Intl. - Caribbean Flights