Find cheap flights from Islip to Caribbean

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

ISP — Caribbean
Jun 17 — Jun 241
Round-trip
1 adult
Economy
0 bags
From?
To?
Fri 6/17
Fri 6/24

Good to know

Low season

May

High season

November

Average price round-trip

$1,234

Good deal round-trip

$804

Good deal one-way

$104
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 90% increase in price.
(avg. price over the last 2 weeks)
or less
or 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 32% 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

FAQs - booking Caribbean flights

Top airlines flying Islip Long Island to Caribbean

Scores according to KAYAK customer reviews
7.2
American AirlinesOverall score based on 47662 reviews
7.5Boarding
7.1Comfort
7.9Crew
6.9Entertainment
6.7Food
Airline reviews

Just perfect

Read more about American Airlines

Just perfect

It was a 10

The boarding process was uneventful and normal. The plane was on the smaller side and a tight fit. Most people had to plane side check their luggage. The pilots seemed pleasant. We waited about an hour from leaving the gate to actually taking off with no information from the crew as to what was taking longer than normal. The flight attendants were informative but aggressive about the mask policy and spoke on the PA system often and for long periods of time. The attitude of the flight crew about several issues made the passengers tense. We arrived about 30 minutes behind schedule but safely.

For a delayed flight, and one that most choose because of the amenities, no one apologized for the lack of amenities. A simple, “we are truly sorry” announced to everyone would have gone miles. Instead, the crew kept trying to almost conceal the total lack of available entertainment and even feign like it might “sort of work” until the last minute. I was traveling with my life partner, who intended upon and did work the whole flight (despite zero internet, even for the little time avail that we are aware of when traveling to/from PR), but also with a just turned 6 year old who had been looking forward to using “his own” screen for the last 2 weeks. Underwhelming to say the least. The crew’s apathy didn’t help.

Cons: "Some of the crew had an attitude and the purchased WiFi did not work"
Cons: "Almost 4 hour delay."
Pros: "Crew was snappy in getting people in plane and checking in carry ons since occupancy had been reached."
Cons: "Lack of adjustable headrest on seat."
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"
Cons: "Crampt space, cold cabin"
Pros: "None"
Cons: "Long delay"
Pros: "Movie options were good."
Cons: "The a/c was not working well and t"
Pros: "The service was excellent and the flight on time. Love American."
Cons: "The seats have been refurbished and if you are a plus size the seats are uncomfortable."
Cons: "Flight cancelled and had to travel 60 miles at my expense to a different airport to get another flight same day"
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: "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!!"
Pros: "On time"
Cons: "Cold cabin"
Cons: "The seats are very tight."
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: "Direct flight"
Cons: "Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats"
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: "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!!!"
Cons: "That all the passengers were rechecked at the Gate by TSA without offering any explanation as to why, if it was a domestic flight, why were they requiring ID again. And checking bags."
Pros: "On time smooth"
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: "Friendly staff. Landed early. Offered a free bag."
Cons: "They moved the flight earlier, which was not fun. And, there were no entertainment centers."
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: "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: "Everything"
Cons: "Nothing"
Pros: "Flight crew very welcoming, flight was pleasant."
Cons: "Seating a bit tight. Didn't offer any snacks only ice water."
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: "Everything was on time, no delays."

The flight was on time and the crew was excellent.

Pros: "Nothing"
Cons: "The crew, the turbulence, the screaming kids, the rude people yelling across rows CONSTANTLY, at each other"
Pros: "The time"
Cons: "Everything"
Cons: "Clean, comfortable plane. Smooth ride. Departed on time, arrived ahead of time:)"
Cons: "The fees for the baggage are ridiculous"
Cons: "Flight was delayed. Showed up to destination airport and now gate was assigned so we sat in runway for over 30 min"
Cons: "For budget airline it’s awesome. Couldn’t ask more"
Pros: "I was in row 2 and it had reclining seats."
Cons: "They did not have enough people to push wheelchairs at Mac Arthur airport. My husband had to push me & since we don’t know the airport we had to ask every step we went, they had no signs leading the way."
Cons: "Never happened, the flight was cancelled and never rebooked."
Cons: "The flight was delayed, it was a mess."
Pros: "We finally made it to the destination"
Cons: "the flight was delayed more than once. and it seems to be common on this route"
Pros: "Landing was perfect!"
Pros: "The anouncements in Islip explaining the boarding process and warning people about bringing carry ons that they did not pay for were clear, loud and understandable. Crew was great."
Cons: "the seats hurt my butt, not sure if I could do a longer flight on this plane"
Pros: "Crew was very nice. Boarding was efficient."
Cons: "Snack selections are very limited. If we are paying for it anyway the choices should be a little more varied."
Cons: "3 hours delayed. I was late for a important interview. I lost money because of it"
Pros: "The price is right. I do not take any of the extras, do not be tricked by the website that you have to pick a seat. Charging more for carry on keeps the cabin clear, buy a bottle of water in the airport and skip the in flight food service. Planes are clean, reasonabley comfortable. Crews are professional."
Cons: "Boarding could be better. Why don't they load the back of the plane first? Mostly because people can't learn to get themselves on and off a plane. Get on and sit down. Then on arrivial standing in the isle fumbleling to get their overhead bags."
Pros: "Nothing"
Cons: "Everything. Really bad seats, no room for you. Carry on - charge $50. No free beverages ."
Cons: "Frontier services is the worst."
Cons: "We sat on plane at gate for 1 1/2 hour while crew attempted to fix mechanical problems."
Pros: "Nothing"
Cons: "Got to the airport at 4am for a flight that was supposed to leave at 6am. The flight finally departed at 11:40am. I missed my non-refundable connecting flight and had to book a new flight. All in all I probably lost $300 because of this situation. On top of that it was my birthday."
Pros: "I liked that the gave us food vouchers for our wait"
Cons: "That I really wanted to get home. One person missed is brother’s funeral, another person missed their connecting flight. I thought it was poor planning on frontiers part. Many people were getting very upset with the crew and calling customer service. I felt very bad feeling f the crew and many people who needed to be in Chicago when they promised for us to get there. It was upsetting, just tried to make lemonade out of lemons."
Pros: "Great flight from Islip to MIA. Looked at another review about water on flights and I was told by the crew that water is FREE!"
Cons: "Seats are small but newly redesigned."
Pros: "In flight crew was cordial, warm, professional"
Cons: "Everything else was a sh*tshow: bad information, confused and angry employees, flight was 7-hours late"
Cons: "Poor customer service at service desk"
Cons: "Let's begin with the need to pay for your seat selection. Then the fact that the seats do not recline at all, so you are forced to sit upright the entire flight. Good luck if you are over 5'8", seats are not intended for taller people. Also, how can an airline not have wifi or inflight entertainment. Not a bargain at all. Oh and $45 per checked bag, nice touch. Avoid if possible."
Pros: "Once in air it was uneventful"
Pros: "everything"
Cons: "wished they had free snacks"
Pros: "The price"
Cons: "The seats were uncomfortable, having to pay for a carry on"
Cons: "$200 ticket and I still have to pay $45 to bring a bag?"
Pros: "McArthur Airport and checkin, a breeze. Boarding,stress free. Attitude of crew, at gate and on plane, wonderful. Nice re-seating available before take off."
Cons: "No free snacks."
Pros: "Ease of boarding, and the fact that we took of 30 minutes late and still landed just about on time"
Cons: "Seats are a bit hard and don’t recline at all"
Cons: "There was a lack of communication, our flight was delayed however there was no explanation as to why."
Pros: "Very friendly flight crew!"
Cons: "Nothing."
Pros: "The on board crew do not compare to the quality service in other flights but are much better than the frontier boarding crew"
Cons: "The service was absolutely terrible, the front desk crew did not want to let me in 40 minutes to my flight because they stated I need to be there 2 hrs earlier. This was ofcourse despite me having only a person item and having prepped in order to not have the slightest delay with TSA. I missed all my apartment viewings because of this and an additional flight delay with the replacement flight I purchased. This rendered my trip absolutely useless and an extra cost because I arrived after hours to my car rental and lost my reservation. If I buy a flight, why can't I stand? IF I CANNOT STAND WHY AM I PURCHASING A SEAT SEPERATELY???"
Pros: "Flight crew"
Cons: "Carry-on fee"
Pros: "Crew was friendly and seats were comfortable ."
Cons: "No gluten free food ootions"
Pros: "The price was right"
Cons: "Long lines to check your bags and confusion at the gate in Islip plus seats are uncomfortable on the plane and the only thing they give you for free is water"
Cons: "I purchased through early online check in round trip carryon for $70. But there is no record and had to pay$45. At PDX."
Pros: "Not one thing did I find enjoyable about this flight."
Cons: "First AND LAST time flying with Frontier.. absolutely horrible experience! Delayed flight by 3hours, changed gates twice, and crew was very unpleasant in assisting common needs .. amongst the pilot "joking" about the ordeal. If I could score this airline and experience a negative, I would!! Don't let this happen to you!"
Pros: "Good flight! Very clean plane"
Cons: "Attendants weren't very friendly but they were polite"
Cons: "On a direct from Atlanta to Denver our bag ended up in LA ???? Spent hours of a short two day trip in the airport. Pay the extra money to fly a proper airline. Our return to Atlanta was even worse."
Pros: "Super cheap."
Cons: "It was hot and very cramped and the chairs didn't recline."
Pros: "We brought our pet with us on this trip. The experience was wonderful. We had no problems with Frontier at all. The stewardess were so kind to us. It was such a pleasant flight. I will be flying Frontier again."
Cons: "Nothing"
Pros: "The Fare"
Cons: "Waiting 1 hour for a gate to open in Chicago"
Cons: "pay for seat on aisle, pay for soda, pay for reclining seat, pay for carry on luggage, reading lite out, no reading for a 3 hour flight, not much in-flight service."
Pros: "The times I didn't fly with Frontier"
Cons: "Had a long layover and watched the employee at the counter yell at about 90% of the people who asked her a question. When it was time to board there was no organization between each zone, so zone 4 started boarding with zone 1."
Pros: "overall very satisfying. havent flown in a number of yrs and things have changed a ton. Ur team did a great job. Booked thru Kayak. One suggestions would be a little more forthcoming with additional costs on website. For us newbies. I will fly Frontier again and have a better understanding of the exp. Thanks for 2 nicely done legs. appreciate the effort and the product"
Pros: "I got where I needed to be safely."
Cons: "Extra charges for baggage; late; cramped."
Cons: "They lost my luggage and took over 24 hours to return it to me...."
Cons: "They said weather related. I could not see any bad weather in the county. If it's weather related they won't reimburse for hotel do it cost 150.00 more dollars in hotel and dinner."
COVID-19 information

Safety measures for airlines flying from Islip to Caribbean

Airlines flying from Islip 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 Islip to Caribbean

Mandatory masks

Masks required on board, masks provided on flights from Islip to Caribbean

Social distancing seating

Middle seats unavailable to book on flights from Islip to Caribbean

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Islip to Caribbean

Flexible cancellations

Waiving of change fees. Search flexible flights from Islip to Caribbean

Book cheap flights from Islip to Caribbean

Recent round-trip flight deals

6/18Sat
1 stopFrontier
27h 14mISP-MBJ
6/22Wed
1 stopFrontier
20h 54mMBJ-ISP
$328
6/18Sat
2 stopsFrontier
40h 05mISP-MBJ
6/22Wed
1 stopFrontier
20h 54mMBJ-ISP
$360
9/9Fri
2 stopsAmerican Airlines
18h 58mISP-SJU
9/21Wed
2 stopsAmerican Airlines
14h 58mSJU-ISP
$365
5/28Sat
1 stopMultiple Airlines
29h 14mISP-SJU
6/5Sun
1 stopMultiple Airlines
13h 32mSJU-ISP
$396
6/16Thu
1 stopFrontier
22h 10mISP-SDQ
7/1Fri
1 stopFrontier
9h 37mSDQ-ISP
$396
6/3Fri
2 stopsFrontier
17h 30mISP-SDQ
6/6Mon
2 stopsFrontier
25h 04mSDQ-ISP
$400
6/18Sat
2 stopsFrontier
22h 25mISP-MBJ
6/22Wed
2 stopsFrontier
28h 05mMBJ-ISP
$403
6/16Thu
1 stopFrontier
22h 10mISP-SDQ
6/19Sun
1 stopFrontier
10h 07mSDQ-ISP
$415
6/13Mon
1 stopMultiple Airlines
12h 11mISP-SDQ
6/18Sat
1 stopMultiple Airlines
13h 04mSDQ-ISP
$417
10/14Fri
2 stopsAmerican Airlines
17h 57mISP-SJU
10/22Sat
1 stopAmerican Airlines
20h 08mSJU-ISP
$422
6/2Thu
2 stopsFrontier
44h 45mISP-MBJ
6/6Mon
2 stopsFrontier
22h 01mMBJ-ISP
$424
6/20Mon
1 stopFrontier
18h 11mISP-SDQ
7/11Mon
2 stopsFrontier
24h 03mSDQ-ISP
$427
9/27Tue
2 stopsAmerican Airlines
15h 28mISP-SJU
10/5Wed
2 stopsAmerican Airlines
14h 58mSJU-ISP
$445
6/13Mon
2 stopsMultiple Airlines
18h 27mISP-SDQ
6/18Sat
1 stopMultiple Airlines
13h 04mSDQ-ISP
$449
5/28Sat
2 stopsMultiple Airlines
18h 26mISP-SJU
6/5Sun
1 stopMultiple Airlines
13h 32mSJU-ISP
$449
10/6Thu
1 stopAmerican Airlines
27h 51mISP-SJU
10/11Tue
1 stopAmerican Airlines
25h 08mSJU-ISP
$456
9/16Fri
1 stopAmerican Airlines
21h 10mISP-NAS
9/19Mon
2 stopsAmerican Airlines
10h 11mNAS-ISP
$462
5/28Sat
2 stopsMultiple Airlines
30h 20mISP-SJU
6/5Sun
2 stopsMultiple Airlines
26h 56mSJU-ISP
$465
5/29Sun
1 stopAmerican Airlines
6h 57mISP-SJU
6/5Sun
1 stopAmerican Airlines
9h 34mSJU-ISP
$469
5/28Sat
1 stopMultiple Airlines
29h 14mISP-SJU
6/4Sat
1 stopMultiple Airlines
7h 53mSJU-ISP
$492

Search by stops

Search by airline

Search by price

Recent one-way flight deals

10/14Fri
2 stopsAmerican Airlines
17h 57mISP-SJU
$198
6/3Fri
1 stopAmerican Airlines
7h 21mISP-NAS
$203
6/2Thu
1 stopAmerican Airlines
21h 26mISP-NAS
$214
6/8Wed
1 stopAmerican Airlines
6h 47mISP-SJU
$223
6/29Wed
1 stopAmerican Airlines
7h 21mISP-NAS
$229
10/14Fri
1 stopAmerican Airlines
27h 51mISP-SJU
$236
5/27Fri
2 stopsAmerican Airlines
19h 37mISP-NAS
$239
6/6Mon
1 stopAmerican Airlines
21h 21mISP-NAS
$241
7/19Tue
2 stopsFrontier
20h 15mISP-PUJ
$242
5/31Tue
2 stopsAmerican Airlines
10h 39mISP-NAS
$249
7/1Fri
2 stopsAmerican Airlines
21h 04mISP-NAS
$250
5/27Fri
1 stopAmerican Airlines
19h 39mISP-NAS
$251
7/14Thu
2 stopsFrontier
23h 00mISP-PUJ
$262
7/19Tue
1 stopFrontier
8h 23mISP-PUJ
$282
7/15Fri
2 stopsFrontier
34h 50mISP-PUJ
$322
7/17Sun
1 stopMultiple Airlines
11h 52mISP-PUJ
$346
7/16Sat
1 stopMultiple Airlines
24h 18mISP-PUJ
$377
7/18Mon
1 stopFrontier
23h 37mISP-PUJ
$384
5/25Wed
3 stopsMultiple Airlines
44h 29mISP-MBJ
$424
7/15Fri
1 stopMultiple Airlines
18h 46mISP-PUJ
$531

Search by stops

Search by airline

Search by price

Islip - Caribbean Flights

Departure:

Islip (ISP)United States

Return flight deals:

Caribbean - Islip

Cabin classes:

$259

Browse origins:

$291