$106 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 5/17. 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$498
Santo Domingo
Santo Domingo1 stop$653
Montego Bay
Montego Bay1 stop$589
Oranjestad
Oranjestad1 stop$604
Nassau
Nassau1 stop$515
Simpson Bay
Simpson Bay1 stop$405
St. John's
St. John's2 stops$1,045
Punta Cana
Punta Cana1 stop$498
Santo Domingo
Santo Domingo1 stop$653
Montego Bay
Montego Bay1 stop$589
Oranjestad
Oranjestad1 stop$604
Nassau
Nassau1 stop$515
Simpson Bay
Simpson Bay1 stop$405
St. John's
St. John's2 stops$1,045

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, Jun 5 - Sun, Jun 7
Frontier Logo
11:00 am - 11:22 pm
ISP
-
SJU
12h 22m
1 stop
Frontier Logo
6:00 am - 10:05 am
SJU
-
ISP
28h 05m
1 stop
$212Frontier
Wed, Jul 1 - Thu, Jul 9
Frontier Logo
9:52 pm - 2:09 am
ISP
-
SJU
28h 17m
1 stop
Frontier Logo
3:06 am - 9:58 am
SJU
-
ISP
6h 52m
1 stop
$258Frontier
Fri, Jun 19 - Sun, Jun 21
Frontier Logo
7:50 pm - 12:37 am
ISP
-
SJU
28h 47m
1 stop
Frontier Logo
3:06 am - 8:57 pm
SJU
-
ISP
17h 51m
1 stop
$276Frontier
Mon, May 25 - Fri, Jun 5
Frontier Logo
6:43 pm - 11:59 pm
ISP
-
SJU
29h 16m
1 stop
Frontier Logo
4:46 pm - 5:58 pm
SJU
-
ISP
25h 12m
1 stop
$289Frontier
Sun, Aug 30 - Thu, Sep 3
JetBlue Logo
6:00 am - 12:37 pm
ISP
-
SXM
6h 37m
1 stop
JetBlue Logo
1:42 pm - 10:56 pm
SXM
-
ISP
9h 14m
1 stop
$405JetBlue
Tue, Jun 2 - Tue, Jun 9
JetBlue Logo
2:35 pm - 1:54 am
ISP
-
STI
11h 19m
1 stop
JetBlue Logo
7:21 pm - 11:35 am
STI
-
ISP
16h 14m
1 stop
$444JetBlue
Tue, Aug 25 - Sun, Aug 30
Multiple Airlines Logo
5:27 pm - 10:20 am
ISP
-
PUJ
16h 53m
1 stop
Multiple Airlines Logo
11:45 am - 1:28 pm
PUJ
-
ISP
25h 43m
2 stops
$498Multiple Airlines
Tue, Aug 25 - Sun, Aug 30
Multiple Airlines Logo
5:27 pm - 10:20 am
ISP
-
PUJ
16h 53m
1 stop
Multiple Airlines Logo
11:45 am - 1:28 pm
PUJ
-
ISP
25h 43m
2 stops
$503Multiple Airlines
Sat, Jul 4 - Wed, Jul 15
Southwest Logo
6:05 am - 12:40 pm
ISP
-
NAS
6h 35m
1 stop
Southwest Logo
8:45 am - 10:35 pm
NAS
-
ISP
13h 50m
2 stops
$580Southwest
Mon, Sep 14 - Mon, Sep 21
Southwest Logo
6:45 am - 1:50 pm
ISP
-
STT
7h 05m
1 stop
Southwest Logo
2:35 pm - 9:30 pm
STT
-
ISP
6h 55m
1 stop
$588Southwest
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 $106 (return) on average. On the other hand, the most expensive months are February and October, when the average cost of round-trip tickets is $865 and $608 respectively.

Good to know

Low seasonMarch
Cheapest flight$106
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 26% 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.
7.9
SouthwestOverall score based on 4305 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

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

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

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

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

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!!!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports