$106 Find Cheap Flights from Islip to Caribbean Islands

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 Islands 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Islip to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Islip to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Islip to Caribbean Islands

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 Islands 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 Islands 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 Islands

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
6:00 am - 9:58 am
SJU
-
ISP
27h 58m
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, May 29
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 Islands flights

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

Can I save money by flying with a layover from Islip to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $279, prices are generally cheapest when you fly direct.

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 Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Islip to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Islip to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Islip to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Islip to Caribbean Islands? 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
DeltaOverall score based on 8459 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

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

2.0 MediocreNicholas, Apr 2026
LGA - CLT
Read more Delta reviews

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports