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$87+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — SJU
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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Cheap 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 December 22, 2025.

This CheapOair deal was found by Cheapflights users on 12/21. 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 12/298:35 pmISP - SJU
1 stop11h 48mFrontier
Thu 1/110:08 amSJU - ISP
1 stop14h 23mFrontier
Deal found 12/21$346
This CheapOair deal was found by Cheapflights users on 12/21. 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 12/246:00 amISP - SJU
1 stop25h 58mFrontier
Thu 1/294:36 pmSJU - ISP
1 stop29h 11mFrontier
Deal found 12/21$373
This CheapOair deal was found by Cheapflights users on 12/21. 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 12/245:27 pmISP - SJU
1 stop21h 32mFrontier
Wed 12/319:37 pmSJU - ISP
1 stop14h 48mFrontier
Deal found 12/21$385
This CheapOair deal was found by Cheapflights users on 12/20. 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 12/298:35 pmISP - SJU
1 stop29h 15mFrontier
Fri 1/96:18 pmSJU - ISP
1 stop25h 50mFrontier
Deal found 12/20$388
This CheapOair deal was found by Cheapflights users on 12/20. 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.
Tue 12/3012:20 pmISP - SJU
1 stop20h 03mFrontier
Thu 1/86:15 amSJU - ISP
1 stop14h 30mFrontier
Deal found 12/20$404
This CheapOair deal was found by Cheapflights users on 12/20. 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.
Thu 12/256:00 amISP - SJU
1 stop25h 58mFrontier
Sun 12/2810:33 pmSJU - ISP
1 stop26h 26mFrontier
Deal found 12/20$410
This CheapOair deal was found by Cheapflights users on 12/20. 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 12/315:27 pmISP - SJU
1 stop14h 56mFrontier
Mon 1/510:08 amSJU - ISP
1 stop14h 51mFrontier
Deal found 12/20$423
This CheapOair deal was found by Cheapflights users on 12/21. 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 12/246:00 amISP - SJU
1 stop12h 28mFrontier
Thu 1/110:08 amSJU - ISP
1 stop14h 23mFrontier
Deal found 12/21$426
This CheapOair deal was found by Cheapflights users on 12/21. 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 12/246:00 amISP - SJU
1 stop25h 58mFrontier
Sun 12/286:00 amSJU - ISP
1 stop14h 40mFrontier
Deal found 12/21$460
This CheapOair deal was found by Cheapflights users on 12/22. 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 12/298:35 pmISP - SJU
1 stop11h 48mFrontier
Sun 1/43:55 amSJU - ISP
1 stop10h 14mFrontier
Deal found 12/22$473
This CheapOair deal was found by Cheapflights users on 12/22. 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 12/298:35 pmISP - SDQ
1 stop13h 45mFrontier
Sun 1/1110:56 amSDQ - ISP
1 stop9h 49mFrontier
Deal found 12/22$504
This CheapOair deal was found by Cheapflights users on 12/19. 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 12/298:35 pmISP - SDQ
1 stop13h 45mFrontier
Mon 1/512:35 pmSDQ - ISP
1 stop8h 04mFrontier
Deal found 12/19$564

Find flight deals from Islip to Caribbean

Keep the following information in mind while searching for Islip to Caribbean flight deals. Data was last updated December 22, 2025.

Round-trip from

$173
(CheapOair)

One-way from

$87
(CheapOair)

Popular in

December

Cheapest in

March

Average price

$363
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. 7% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 22, 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

Sat 2/21

8:23 pm-2:53 am

1 stop29h 30m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:25 pm-2:39 pm

1 stop22h 14m

$173

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Sat 2/28

8:23 pm-2:53 am

1 stop29h 30m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-2:39 pm

1 stop22h 14m

$173

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Mon 2/23

2:17 pm-2:25 am

1 stop11h 08m

San Juan Luis Munoz Marin Intl

Sat 2/28

5:25 pm-7:48 am

1 stop15h 23m

$177

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Thu 1/8

8:40 pm-11:20 am

1 stop13h 40m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:55 am-12:57 pm

1 stop7h 02m

$180

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Mon 1/5

8:24 pm-2:50 am

1 stop29h 26m

San Juan Luis Munoz Marin Intl

Fri 1/9

3:55 am-7:08 pm

1 stop16h 13m

$181

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Thu 2/26

5:07 pm-2:25 am

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Mon 3/2

3:53 am-8:40 am

1 stop29h 47m

$181

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Mon 1/5

8:24 pm-12:17 am

1 stop26h 53m

San Juan Luis Munoz Marin Intl

Mon 1/12

9:23 pm-10:46 pm

1 stop26h 23m

$181

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Sat 1/10

7:56 pm-8:54 am

1 stop11h 58m

San Juan Luis Munoz Marin Intl

Wed 1/14

8:57 am-8:55 am

1 stop24h 58m

$181

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Thu 1/8

8:40 pm-8:54 am

1 stop11h 14m

San Juan Luis Munoz Marin Intl

Mon 1/12

3:58 am-10:46 pm

1 stop19h 48m

$181

IslipSan Juan

ISP - SJU

ISPSJU

Islip Long Island

Thu 1/15

8:45 pm-2:30 am

1 stop28h 45m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:00 am-6:48 pm

1 stop11h 48m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 53 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 December 22, 2025.

It’s optimal to fly from Islip, New York to Caribbean at noon. By choosing this option you can save up to 48% on the cost of your flight, compared to a flight in the morning.

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 December 22, 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
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,895 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,078 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $369, Frontier can have you in Caribbean from Islip, New York in 8h 53m. Airlines will cover a distance of 1116 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 - Nassau Intl, 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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Alternative routes for Islip to Caribbean

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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$111Average$220FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$216Average$377FlexibilityNo cancel feeOn-time62%
DeltaCheapest$350Average$402FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$367Average$535FlexibilityNo cancel feeOn-time63%

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