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$69+ Cheap flights from Islip, NY (ISP) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — SJU
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Find flight deals from Islip to Caribbean

Cheapest flights from Islip to Caribbean
Explore the most affordable flight options available from Islip to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2025.

This CheapOair deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:00 amISP - SJU
1 stop16h 56mFrontier
Tue 12/93:55 amSJU - ISP
1 stop19h 49mFrontier
Deal found 11/4$138
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:58 pmISP - SJU
1 stop17h 21mFrontier
Thu 11/207:15 amSJU - ISP
1 stop28h 22mFrontier
Deal found 11/3$168
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:00 amISP - SJU
1 stop16h 56mFrontier
Sun 12/75:09 pmSJU - ISP
1 stop17h 04mFrontier
Deal found 11/3$216
This CheapOair deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amISP - SJU
1 stop26h 55mFrontier
Sat 12/133:55 amSJU - ISP
1 stop7h 25mFrontier
Deal found 11/5$231
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:58 pmISP - SJU
1 stop17h 21mFrontier
Mon 11/246:10 amSJU - ISP
1 stop18h 49mFrontier
Deal found 11/3$237
This CheapOair deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:00 amISP - SJU
1 stop16h 56mFrontier
Mon 12/85:09 pmSJU - ISP
1 stop27h 25mFrontier
Deal found 11/4$251
This CheapOair deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:00 amISP - SJU
1 stop16h 56mFrontier
Fri 12/1910:08 amSJU - ISP
1 stop14h 51mFrontier
Deal found 11/4$252
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/194:58 pmISP - SJU
2 stops26h 29mMultiple Airlines
Sat 11/223:59 amSJU - ISP
1 stop7h 10mMultiple Airlines
Deal found 11/4$255
This CheapOair deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/124:58 pmISP - SJU
1 stop8h 56mFrontier
Mon 11/173:59 amSJU - ISP
1 stop14h 43mFrontier
Deal found 11/4$266
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:58 pmISP - SJU
1 stop17h 21mFrontier
Wed 12/318:36 pmSJU - ISP
1 stop27h 55mFrontier
Deal found 11/3$277
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:58 pmISP - PUJ
1 stop18h 47mMultiple Airlines
Sat 11/226:50 pmPUJ - ISP
2 stops16h 19mMultiple Airlines
Deal found 11/4$351
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:20 pmISP - PUJ
2 stops27h 30mMultiple Airlines
Thu 12/253:08 pmPUJ - ISP
1 stop23h 01mMultiple Airlines
Deal found 11/3$473

Cheap flight deals from Islip to Caribbean

Keep the following information in mind while searching for Islip to Caribbean flight deals. Data was last updated November 5, 2025.

Round-trip from

$138
(CheapOair)

One-way from

$69
(CheapOair)

Popular in

December

Cheapest in

March

Average price

$266
From Islip Long Island to Caribbean
Search Deals
One-way flight from Islip Long Island to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 5, 2025.
Use the filters below to find and compare flights from Islip to Caribbean that are best for you.

Fly from

Islip

Fly to

Caribbean

Route

Depart

Return

Price

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Thu 1/15

8:15 pm-12:46 am

1 stop27h 31m

San Juan Luis Munoz Marin Intl

Thu 1/22

11:05 am-10:40 am

1 stop24h 35m

$153

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Sun 1/11

3:34 pm-9:55 am

1 stop17h 21m

San Juan Luis Munoz Marin Intl

Thu 1/15

7:00 am-7:26 pm

1 stop13h 26m

$153

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Fri 1/23

11:35 am-9:55 am

1 stop21h 20m

San Juan Luis Munoz Marin Intl

Sat 1/31

3:55 am-10:40 am

1 stop7h 45m

$168

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Sun 1/18

3:34 pm-9:54 am

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Sat 1/24

3:55 am-10:40 am

1 stop7h 45m

$216

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Sun 2/22

10:42 am-8:32 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Wed 2/25

3:55 am-9:47 am

1 stop6h 52m

$231

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Thu 1/22

11:35 am-9:55 am

1 stop21h 20m

San Juan Luis Munoz Marin Intl

Wed 1/28

11:05 am-10:40 am

1 stop24h 35m

$231

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Fri 12/5

6:00 am-11:56 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

Mon 12/8

5:09 pm-7:34 pm

1 stop27h 25m

$251

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Sat 12/6

10:19 am-9:55 am

1 stop22h 36m

San Juan Luis Munoz Marin Intl

Sat 12/13

3:55 am-10:20 am

1 stop7h 25m

$251

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Tue 1/27

9:40 am-5:35 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Wed 2/4

6:00 am-11:35 am

1 stop6h 35m

$274

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Tue 2/3

12:25 pm-8:02 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:00 am-11:35 am

1 stop6h 35m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 60 results
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Best time to book a flight from Islip to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Islip with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Islip to Caribbean

What is the cheapest month to book a flight from Islip, New York to Caribbean?

Currently, February is the cheapest month in which you can book a flight from Islip, New York to Caribbean (average of $59). Flying from Islip, New York to Caribbean in August is currently the most expensive (average of $138). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ISP to CB?

Find hourly flight availability from Islip to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 5, 2025.

It’s optimal to fly from Islip, New York to Caribbean in the evening. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight at noon.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated November 5, 2025.
Read through reviews of airlines operating flights from Islip to Caribbean, such as Southwest, Delta, and JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,004 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,908 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,115 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Islip to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Islip to Caribbean?

    Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Caribbean. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

  • How long is the flight from Islip, New York to Caribbean?

    For as low as $153, Frontier can have you in Caribbean from Islip, New York in 17h 20m. Airlines will cover a distance of 1599 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Islip, New York to Caribbean?

    While some choose either Islip Long Island - Santo Domingo Las Americas or Islip Long Island - Punta Cana, Islip Long Island - San Juan Luis Munoz Marin Intl is the most popular route from Islip, New York to Caribbean.

  • Can I find deals for flights from Islip to Caribbean that include hotel bookings?

    Yes. In addition to deals on Islip to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Caribbean.

  • Can I find deals for business class flights from Islip to Caribbean?

    Yes. Cheapflights offers flight deals from Islip to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Islip, New York to Caribbean?

    Currently, February is the cheapest month in which you can book a flight from Islip, New York to Caribbean (average of $59). Flying from Islip, New York to Caribbean in August is currently the most expensive (average of $138). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Islip to Caribbean

Discover the top 4 airlines that operate flights from Islip to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$111Average$220FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$216Average$372FlexibilityNo cancel feeOn-time62%
DeltaCheapest$350Average$402FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$367Average$728FlexibilityNo cancel feeOn-time63%

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