$141 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 10/3. 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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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$384
Santo Domingo
Santo Domingo1 stop$444
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$1,000
Nassau
Nassau1 stop$562
Kingston
Kingston1 stop$611
George Town
George Town1 stop$1,926
Punta Cana
Punta Cana1 stop$384
Santo Domingo
Santo Domingo1 stop$444
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$1,000
Nassau
Nassau1 stop$562
Kingston
Kingston1 stop$611
George Town
George Town1 stop$1,926

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 3 - Sat, Oct 4
Frontier Logo
5:05 pm - 12:00 amISP-SJU
6h 55m1 stop
Frontier Logo
3:39 am - 10:37 amSJU-ISP
6h 58m1 stop
$280Frontier
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Sat, Sep 20 - Fri, Sep 26
Frontier Logo
5:05 pm - 12:00 amISP-SJU
6h 55m1 stop
Frontier Logo
3:39 am - 10:40 amSJU-ISP
7h 01m1 stop
$281Frontier
Find Deal
Sat, Aug 30 - Fri, Sep 5
Frontier Logo
7:33 pm - 2:50 amISP-SJU
7h 17m1 stop
Frontier Logo
8:00 am - 4:27 pmSJU-ISP
8h 27m1 stop
$284Frontier
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Tue, Sep 16 - Tue, Sep 30
Frontier Logo
11:25 am - 2:34 amISP-SJU
15h 09m1 stop
Frontier Logo
4:42 pm - 10:40 amSJU-ISP
17h 58m1 stop
$285Frontier
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Tue, Oct 28 - Fri, Oct 31
JetBlue Logo
12:15 pm - 9:29 pmISP-SJU
9h 14m1 stop
JetBlue Logo
4:05 am - 11:18 amSJU-ISP
7h 13m1 stop
$322JetBlue
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Fri, Sep 19 - Mon, Sep 22
JetBlue Logo
11:35 am - 8:19 pmISP-SJU
8h 44m1 stop
JetBlue Logo
7:00 am - 2:44 pmSJU-ISP
7h 44m1 stop
$353JetBlue
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Wed, Nov 12 - Wed, Nov 19
Southwest Logo
12:55 pm - 12:35 amISP-SJU
10h 40m2 stops
Southwest Logo
6:40 am - 12:15 pmSJU-ISP
6h 35m1 stop
$383Southwest
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Thu, Aug 21 - Mon, Aug 25
 Logo
7:33 pm - 11:56 amISP-SDQ
16h 23m1 stop
 Logo
5:05 pm - 11:59 pmSDQ-ISP
30h 54m2 stops
Fri, Aug 29 - Fri, Sep 5
 Logo
7:33 pm - 11:36 amISP-PUJ
16h 03m1 stop
 Logo
3:19 pm - 10:40 amPUJ-ISP
19h 21m2 stops
Thu, Oct 9 - Mon, Oct 13
Southwest Logo
5:30 am - 11:20 amISP-MBJ
6h 50m1 stop
Southwest Logo
12:20 pm - 11:45 pmMBJ-ISP
10h 25m1 stop
$947Southwest
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Booking Insights

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$141
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 4241 reviews
8.1Boarding
7.6Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

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

flight was delayed for hours with no explanation. The plane was a very old aircraft.

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.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

Everything you need to know for your flight to Caribbean

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