$88 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 5/1. 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 Cana2 stops$337
Santo Domingo
Santo Domingo1 stop$539
Montego Bay
Montego Bay2 stops$399
Oranjestad
Oranjestad1 stop$562
Nassau
Nassau1 stop$418
Kingston
Kingston1 stop$519
Simpson Bay
Simpson Bay1 stop$608
Providenciales
Providenciales1 stop$569
George Town
George Town1 stop$525
St. John's
St. John's2 stops$1,117
Punta Cana
Punta Cana2 stops$337
Santo Domingo
Santo Domingo1 stop$539
Montego Bay
Montego Bay2 stops$399
Oranjestad
Oranjestad1 stop$562
Nassau
Nassau1 stop$418
Kingston
Kingston1 stop$519
Simpson Bay
Simpson Bay1 stop$608
Providenciales
Providenciales1 stop$569
George Town
George Town1 stop$525
St. John's
St. John's2 stops$1,117

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

Fri, May 1 - Sat, May 2
Frontier Logo
4:07 pm - 2:01 am
ISP
-
SJU
9h 54m
1 stop
Frontier Logo
9:58 am - 9:13 am
SJU
-
ISP
23h 15m
1 stop
$176Frontier
Fri, May 8 - Sun, May 10
Frontier Logo
6:59 pm - 2:01 pm
ISP
-
SJU
19h 02m
1 stop
Frontier Logo
3:03 am - 10:05 am
SJU
-
ISP
7h 02m
1 stop
$186Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
4:07 pm - 2:01 am
ISP
-
SJU
9h 54m
1 stop
Frontier Logo
6:30 am - 11:00 am
SJU
-
ISP
28h 30m
1 stop
$194Frontier
Wed, May 6 - Sun, May 10
Frontier Logo
11:00 am - 2:08 am
ISP
-
SJU
15h 08m
1 stop
Frontier Logo
3:33 pm - 10:05 am
SJU
-
ISP
18h 32m
1 stop
$196Frontier
Mon, May 4 - Thu, May 14
JetBlue Logo
6:40 pm - 7:21 am
ISP
-
STI
12h 41m
1 stop
JetBlue Logo
8:57 am - 8:04 pm
STI
-
ISP
11h 07m
1 stop
$364JetBlue
Mon, May 4 - Fri, May 8
JetBlue Logo
8:59 pm - 8:03 am
ISP
-
STI
11h 04m
1 stop
JetBlue Logo
8:57 am - 8:04 pm
STI
-
ISP
11h 07m
1 stop
$411JetBlue
Mon, Apr 27 - Fri, May 1
Southwest Logo
6:50 am - 1:45 pm
ISP
-
AUA
6h 55m
1 stop
Southwest Logo
2:35 pm - 10:30 pm
AUA
-
ISP
7h 55m
1 stop
$596Southwest
Sat, Jul 25 - Sat, Aug 1
Southwest Logo
5:35 am - 3:05 pm
ISP
-
SXM
9h 30m
1 stop
Southwest Logo
4:05 pm - 11:10 pm
SXM
-
ISP
7h 05m
1 stop
$608Southwest
Fri, Jul 10 - Fri, Jul 24
Multiple Airlines Logo
6:00 am - 3:17 pm
ISP
-
STT
33h 17m
2 stops
Multiple Airlines Logo
5:40 pm - 9:14 am
STT
-
ISP
15h 34m
2 stops
$861Multiple Airlines
Fri, Jul 10 - Fri, Jul 24
Multiple Airlines Logo
6:00 am - 3:17 pm
ISP
-
STT
33h 17m
2 stops
Multiple Airlines Logo
1:46 pm - 9:14 am
STT
-
ISP
19h 28m
2 stops
$916Multiple Airlines
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 January, when tickets cost $290 (return) on average. On the other hand, the most expensive months are February and October, when the average cost of round-trip tickets is $871 and $608 respectively.

Good to know

Low seasonMarch
Cheapest flight$88
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 16% increase in price.
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.

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.
8.0
SouthwestOverall score based on 4339 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

2.0 MediocreJames, Apr 2026
LAX - MCO
Read more Southwest reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

I am still at the Airport! Delayed Delayed and Delyaed

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Delayed. Hot. Passenger next to me was so large I couldn’t move.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

Not a pleasant experience, service was poor. Didn't like it

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.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports