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Grand Cayman

$534+ Cheap flights from Islip, NY (ISP) to Grand Cayman

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — GCM
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap flight deals from Islip to Grand Cayman

Cheapest flights from Islip to Grand Cayman
Explore the most affordable flight options available from Islip to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.

This JetBlue deal was found by Cheapflights users on 1/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/288:25 am
ISP
-
GCM
1 stop5h 25m
JetBlue
Sat 4/42:20 pm
GCM
-
ISP
1 stop7h 26m
JetBlue
Deal found 1/18$534
This Southwest deal was found by Cheapflights users on 1/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/126:35 am
ISP
-
GCM
1 stop6h 20m
Southwest
Tue 2/171:50 pm
GCM
-
ISP
1 stop8h 20m
Southwest
Deal found 1/19$757
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/136:35 am
ISP
-
GCM
1 stop6h 20m
Southwest
Tue 2/171:50 pm
GCM
-
ISP
1 stop8h 20m
Southwest
Deal found 1/20$817
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:20 am
ISP
-
GCM
1 stop6h 35m
Southwest
Tue 2/241:50 pm
GCM
-
ISP
2 stops8h 05m
Southwest
Deal found 1/20$912

Find flight deals from Islip to Grand Cayman

Keep the following information in mind while searching for Islip to Grand Cayman flight deals. Data was last updated January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$534
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$370
Provider with most accurate pricing for New York (NYC)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-George Town Owen Roberts Intl flights.
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From Islip Long Island to Grand Cayman
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Grand Cayman 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 January 20, 2026.
Use the filters below to find and compare flights from Islip to Grand Cayman that are best for you.

Fly from

Islip

Fly to

Grand Cayman

Route

Depart

Return

Price

IslipGeorge Town

ISP - GCM

ISPGCM

Islip Long Island

Sat 3/28

8:25 am-12:50 pm

1 stop5h 25m

George Town Owen Roberts Intl

Sat 4/4

2:20 pm-10:46 pm

1 stop7h 26m

$534

IslipGeorge Town

ISP - GCM

ISPGCM

Islip Long Island

Thu 2/12

6:35 am-12:55 pm

1 stop6h 20m

George Town Owen Roberts Intl

Tue 2/17

1:50 pm-10:10 pm

1 stop8h 20m

$757

IslipGeorge Town

ISP - GCM

ISPGCM

Islip Long Island

Fri 2/13

6:35 am-12:55 pm

1 stop6h 20m

George Town Owen Roberts Intl

Tue 2/17

1:50 pm-10:10 pm

1 stop8h 20m

$817

IslipGeorge Town

ISP - GCM

ISPGCM

Islip Long Island

Tue 2/17

6:20 am-12:55 pm

1 stop6h 35m

George Town Owen Roberts Intl

Tue 2/24

1:50 pm-9:55 pm

2 stops8h 05m

$912

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Best time to book a flight from Islip to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman

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

Currently, October is the cheapest month in which you can book a flight from Islip, New York to Grand Cayman (average of $119). Flying from Islip, New York to Grand Cayman in June is currently the most expensive (average of $332). 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.

Related info for your journey

Find useful and relevant information for your journey from Islip to Grand Cayman. 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 Grand Cayman?

    Islip Long Island (ISP) is the airport you will fly out of if you book a flight from Islip to Grand Cayman. It is only a 7.2 mi journey to Long Island (ISP) from Islip’s city center.

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

    A quick flight from Islip, New York to Grand Cayman can take about 5h 25m. JetBlue provides one of the quickest options available for as low as $534. There are 1562 mi between Islip, New York and Grand Cayman. This flight may include one or multiple stops.

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

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

  • How can I find direct flights from Islip to Grand Cayman?

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

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

    Yes. Cheapflights offers flight deals from Islip to Grand Cayman 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 Grand Cayman?

    Currently, October is the cheapest month in which you can book a flight from Islip, New York to Grand Cayman (average of $119). Flying from Islip, New York to Grand Cayman in June is currently the most expensive (average of $332). 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

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