$69 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 1/18. 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, 0 bags

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Cheap Flights from Islip to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$466
Santo Domingo
Santo Domingo1 stop$410
Montego Bay
Montego Bay1 stop$447
Oranjestad
Oranjestad1 stop$1,058
Nassau
Nassau2 stops$493
Kingston
Kingston1 stop$1,045
Simpson Bay
Simpson Bay2 stops$464
Punta Cana
Punta Cana1 stop$466
Santo Domingo
Santo Domingo1 stop$410
Montego Bay
Montego Bay1 stop$447
Oranjestad
Oranjestad1 stop$1,058
Nassau
Nassau2 stops$493
Kingston
Kingston1 stop$1,045
Simpson Bay
Simpson Bay2 stops$464

Book Cheap Islip to Caribbean Plane Tickets

 
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

seg, fev 2 - ter, fev 10
Frontier Logo
7:43 pm - 11:59 pmISP-SJU
27h 16m1 stop
Frontier Logo
11:05 am - 10:40 amSJU-ISP
24h 35m1 stop
$138Frontier
Find Deal
sáb, fev 21 - sex, fev 27
Frontier Logo
7:41 pm - 9:55 amISP-SJU
13h 14m1 stop
Frontier Logo
3:55 am - 10:40 amSJU-ISP
7h 45m1 stop
$153Frontier
Find Deal
sex, fev 27 - qui, mar 5
Frontier Logo
5:03 pm - 9:55 amISP-SJU
15h 52m1 stop
Frontier Logo
3:55 am - 7:11 pmSJU-ISP
16h 16m1 stop
$168Frontier
Find Deal
sáb, jan 10 - sáb, jan 17
Frontier Logo
7:56 pm - 11:16 amISP-SJU
14h 20m1 stop
Frontier Logo
3:47 pm - 12:57 pmSJU-ISP
22h 10m1 stop
$212Frontier
Find Deal
sex, dez 5 - qua, dez 10
Multiple Airlines Logo
8:29 pm - 9:55 amISP-SJU
12h 26m1 stop
Multiple Airlines Logo
5:00 pm - 9:13 amSJU-ISP
17h 13m1 stop
$214Multiple Airlines
Find Deal
ter, dez 9 - ter, dez 16
JetBlue Logo
10:45 am - 3:35 pmISP-MBJ
28h 50m1 stop
JetBlue Logo
4:52 pm - 9:55 amMBJ-ISP
17h 03m1 stop
$447JetBlue
Find Deal
seg, jan 12 - qua, jan 21
JetBlue Logo
12:25 pm - 2:28 pmISP-SXM
25h 03m2 stops
JetBlue Logo
4:25 pm - 11:35 amSXM-ISP
20h 10m1 stop
$464JetBlue
Find Deal
sáb, jan 10 - qua, jan 14
Multiple Airlines Logo
6:00 am - 10:30 amISP-NAS
28h 30m2 stops
Multiple Airlines Logo
12:00 pm - 10:46 pmNAS-ISP
10h 46m1 stop
$493Multiple Airlines
Find Deal
ter, dez 9 - ter, dez 16
Southwest Logo
5:40 am - 2:55 pmISP-MBJ
9h 15m2 stops
Southwest Logo
1:50 pm - 9:40 pmMBJ-ISP
7h 50m1 stop
$532Southwest
Find Deal
sáb, jan 10 - qua, jan 14
Southwest Logo
5:45 am - 1:25 pmISP-NAS
7h 40m2 stops
Southwest Logo
1:55 pm - 9:55 pmNAS-ISP
8h 00m2 stops
$549Southwest
Find Deal
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 February, when tickets cost $210 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $943 and $673 respectively.

Good to know

Low seasonJuly
Cheapest flight$69
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 50% 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 4 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.
7.9
SouthwestOverall score based on 4238 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

10.0 ExcellentMichael, Nov 2025LAX - BWI
Read more Southwest reviews

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

I truly love flying with Delta. They have always treated me with the upmost respect

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight was great. The gate location was way to far away!!!

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

I believe that a four-hour trip should have a meal. Delta had none.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

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.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports