Find cheap flights from Long Island to Caribbean from $99

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 7/10. 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.
Round-trip
1 adult
Economy
0 bags
Sun 7/2
Sun 7/9

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Latest Caribbean Flight Deals

Best round-trip prices found by our users on KAYAK in the last 72 hours

MOST POPULARPunta Cana
1 stop from $391
Montego Bay
1 stop from $389
Santo Domingo
1 stop from $364

Good to know

Low season

September

High season

December

Cheapest flight

$99

Average price round-trip

$371
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Islip to San Juan
(price for this month)

Top tips for finding cheap flights to Caribbean

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly from Long Island is May.
  • Morning departure is around 36% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean flights

Top airline flying from Islip to Caribbean

Scores according to KAYAK customer reviews
5.7
FrontierOverall score based on 39623 reviews
60overall
47food
68crew
46entertainment
54comfort
64boarding
Airline reviews
Pros: "Nothing"
Cons: "The crew, the turbulence, the screaming kids, the rude people yelling across rows CONSTANTLY, at each other"
Read more about Frontier
Pros: "Nothing"
Cons: "The crew, the turbulence, the screaming kids, the rude people yelling across rows CONSTANTLY, at each other"
Pros: "It was ok, one gets what one pays and I understand that."
Cons: "Some padding on the chairs would have been welcome."
Pros: "The crew of the flight was good but the seat are no comfortable."
Cons: "Comfortable seats."
Pros: "Once again everyone was so wonderful and helpful"
Cons: "Lower luggage cost. I spent $110 additional on this trip since since I wasn't well informed (my fault)"
Cons: "Clean, comfortable plane. Smooth ride. Departed on time, arrived ahead of time:)"
Cons: "Flight was delayed. Showed up to destination airport and now gate was assigned so we sat in runway for over 30 min"
Cons: "For the price, you cannot go wrong. Would recommend and travel again with this airline."
Cons: "For budget airline it’s awesome. Couldn’t ask more"
Pros: "I was in row 2 and it had reclining seats."
Cons: "They did not have enough people to push wheelchairs at Mac Arthur airport. My husband had to push me & since we don’t know the airport we had to ask every step we went, they had no signs leading the way."
Pros: "We finally made it to the destination"
Cons: "the flight was delayed more than once. and it seems to be common on this route"

Book cheap flights from Long Island to Caribbean

Recent round-trip flight deals

7/1Sat
1 stopFrontier
17h 03mISP-SJU
7/8Sat
1 stopFrontier
16h 34mSJU-ISP
$240
10/5Thu
1 stopFrontier
10h 12mISP-SJU
10/10Tue
1 stopFrontier
7h 31mSJU-ISP
$273
6/29Thu
1 stopFrontier
7h 25mISP-SJU
7/3Mon
1 stopFrontier
7h 20mSJU-ISP
$283
7/1Sat
1 stopFrontier
17h 03mISP-SJU
7/7Fri
1 stopFrontier
7h 10mSJU-ISP
$290
6/29Thu
1 stopMultiple Airlines
14h 12mISP-SJU
7/4Tue
1 stopMultiple Airlines
16h 50mSJU-ISP
$301
6/29Thu
1 stopMultiple Airlines
14h 12mISP-SJU
7/3Mon
2 stopsMultiple Airlines
20h 51mSJU-ISP
$327
6/22Thu
1 stopFrontier
7h 25mISP-SJU
6/26Mon
1 stopFrontier
7h 15mSJU-ISP
$333
6/19Mon
2 stopsMultiple Airlines
18h 40mISP-SJU
6/21Wed
1 stopMultiple Airlines
13h 38mSJU-ISP
$334
6/19Mon
2 stopsFrontier
18h 40mISP-SJU
6/20Tue
1 stopFrontier
11h 49mSJU-ISP
$336
6/19Mon
1 stopFrontier
6h 46mISP-SJU
6/20Tue
1 stopFrontier
11h 49mSJU-ISP
$338
6/29Thu
1 stopMultiple Airlines
14h 12mISP-SJU
7/4Tue
2 stopsMultiple Airlines
18h 28mSJU-ISP
$342
6/23Fri
1 stopFrontier
6h 51mISP-SJU
6/26Mon
1 stopFrontier
7h 15mSJU-ISP
$343
6/19Mon
2 stopsFrontier
18h 40mISP-SJU
6/20Tue
1 stopFrontier
11h 49mSJU-ISP
$344
7/13Thu
1 stopFrontier
21h 29mISP-MBJ
7/29Sat
1 stopFrontier
7h 51mMBJ-ISP
$389
7/1Sat
2 stopsMultiple Airlines
16h 58mISP-SJU
7/7Fri
1 stopMultiple Airlines
14h 33mSJU-ISP
$411
7/1Sat
1 stopMultiple Airlines
9h 16mISP-SJU
7/8Sat
2 stopsMultiple Airlines
17h 34mSJU-ISP
$441
6/22Thu
2 stopsMultiple Airlines
14h 13mISP-SJU
6/27Tue
2 stopsMultiple Airlines
17h 06mSJU-ISP
$443
6/22Thu
3 stopsMultiple Airlines
37h 04mISP-SJU
6/27Tue
2 stopsMultiple Airlines
17h 06mSJU-ISP
$478
6/23Fri
2 stopsMultiple Airlines
12h 52mISP-SJU
6/27Tue
2 stopsMultiple Airlines
17h 06mSJU-ISP
$480
6/22Thu
3 stopsMultiple Airlines
37h 04mISP-SJU
6/27Tue
3 stopsMultiple Airlines
28h 25mSJU-ISP
$518

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Recent one-way flight deals

7/10Mon
1 stopFrontier
11h 37mISP-SJU
$99
7/23Sun
1 stopFrontier
16h 44mISP-SJU
$116
7/4Tue
1 stopFrontier
7h 35mISP-SJU
$129
11/11Sat
1 stopFrontier
17h 41mISP-SJU
$134
7/6Thu
1 stopMultiple Airlines
9h 38mISP-SJU
$136
10/27Fri
1 stopFrontier
11h 55mISP-SJU
$144
7/5Wed
1 stopMultiple Airlines
29h 13mISP-SJU
$163
7/4Tue
2 stopsMultiple Airlines
18h 07mISP-SJU
$173
7/5Wed
3 stopsMultiple Airlines
32h 53mISP-SJU
$176
7/5Wed
2 stopsMultiple Airlines
27h 57mISP-SJU
$236
7/6Thu
2 stopsMultiple Airlines
28h 44mISP-SJU
$244
7/4Tue
3 stopsMultiple Airlines
31h 57mISP-SJU
$312

Search by stops

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Islip - Caribbean Flights