$142 Find Cheap Flights from Islip 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 Islip to Caribbean departing on 7/12. 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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Flights Deals

Best Caribbean Flight Deals from Islip

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$395
Santo Domingo
Santo Domingo1 stop$535
Montego Bay
Montego Bay1 stop$608
Oranjestad
Oranjestad1 stop$765
Nassau
Nassau1 stop$637
Saint Thomas Island
Saint Thomas Island2 stops$1,182
Kingston
Kingston2 stops$927
Punta Cana
Punta Cana1 stop$395
Santo Domingo
Santo Domingo1 stop$535
Montego Bay
Montego Bay1 stop$608
Oranjestad
Oranjestad1 stop$765
Nassau
Nassau1 stop$637
Saint Thomas Island
Saint Thomas Island2 stops$1,182
Kingston
Kingston2 stops$927

Cheap Flights from Islip to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Islip 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 Islip to Caribbean

Fri, Oct 31 - Sun, Nov 2
Frontier Logo
5:05 pm - 11:54 pmISP-SJU
6h 49m1 stop
Frontier Logo
3:59 am - 10:37 amSJU-ISP
7h 38m1 stop
$220Frontier
Find Deal
Fri, Sep 12 - Sat, Sep 13
Frontier Logo
5:05 pm - 12:00 amISP-SJU
6h 55m1 stop
Frontier Logo
3:39 am - 10:40 amSJU-ISP
7h 01m1 stop
$270Frontier
Find Deal
Fri, Sep 5 - Sun, Sep 7
Frontier Logo
5:05 pm - 12:00 amISP-SJU
6h 55m1 stop
Frontier Logo
3:39 am - 10:40 amSJU-ISP
7h 01m1 stop
$271Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Frontier Logo
5:05 pm - 12:00 amISP-SJU
6h 55m1 stop
Frontier Logo
3:39 am - 10:40 amSJU-ISP
7h 01m1 stop
$276Frontier
Find Deal
Tue, Jul 15 - Mon, Jul 28
JetBlue Logo
12:35 pm - 11:12 pmISP-SJU
10h 37m1 stop
JetBlue Logo
5:01 am - 12:00 pmSJU-ISP
6h 59m1 stop
$406JetBlue
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Fri, Aug 22 - Mon, Aug 25
JetBlue Logo
11:40 am - 1:58 pmISP-PUJ
26h 18m1 stop
JetBlue Logo
6:35 pm - 11:41 amPUJ-ISP
17h 06m1 stop
$470JetBlue
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Fri, Aug 29 - Sun, Aug 31
 Logo
7:33 pm - 11:56 amISP-SDQ
16h 23m1 stop
 Logo
5:05 pm - 8:08 amSDQ-ISP
15h 03m2 stops
Sat, Aug 16 - Sat, Aug 23
 Logo
8:37 pm - 10:45 amISP-SDQ
14h 08m1 stop
 Logo
5:05 pm - 11:59 pmSDQ-ISP
30h 54m2 stops
Wed, Oct 8 - Mon, Oct 13
Southwest Logo
6:00 am - 2:00 pmISP-MBJ
9h 00m1 stop
Southwest Logo
12:20 pm - 11:45 pmMBJ-ISP
10h 25m1 stop
$608Southwest
Find Deal
Wed, Oct 8 - Mon, Oct 13
Southwest Logo
6:00 am - 1:25 pmISP-MBJ
8h 25m2 stops
Southwest Logo
12:20 pm - 11:45 pmMBJ-ISP
10h 25m1 stop
$612Southwest
Find Deal
Useful Info

KAYAK's insights & trends for Islip to Caribbean flights

Get data-powered insights and trends into flights from Islip to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Islip to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Islip to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Islip to Caribbean is November, when tickets cost $204 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $711 and $673 respectively.


Good to know

Low seasonJuly
High seasonApril
Cheapest flight$142
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Islip to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Islip 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 Islip to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Islip 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 Islip 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 Islip 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 Islip 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 Islip 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 at night, when round-trip flights cost $208 on average. Morning departures are around 27% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $390.

Reviews of the top 3 airlines serving from Islip to Caribbean

 
Need help choosing which airline to fly with from Islip 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.
8.0
SouthwestOverall score based on 4270 reviews
8.2Boarding
7.6Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

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.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Very bad! No good service delayed my second connection flight

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Flight was late. Missed connecting in Denver. My new flight is more than 24 hours later and I have no room, vouchers, or compensation, and might also be bumped from the one tomorrow.

Frontier is terrible. Paid for exit row, not given exit row, refused to refund fee.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

Everything you need to know for your flight to Caribbean

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