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$350+ Cheap flights from Islip to Key West (ISP - EYW)

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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Islip to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$392
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$371
From Islip Long Island to Key West
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Islip to Key West

Cheapest flights from Islip to Key West
Explore the most affordable flight options available from Islip to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Trip.com deal was found by Cheapflights users on 9/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/83:43 pmISP - EYW
1 stop24h 21mMultiple Airlines
Mon 10/133:56 pmEYW - ISP
1 stop17h 48mMultiple Airlines
Deal found 9/11$350
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 9/205:05 pmISP - EYW
1 stop15h 10mMultiple Airlines
Wed 9/249:47 amEYW - ISP
2 stops9h 54mMultiple Airlines
Deal found 9/9$392
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 10/312:25 pmISP - EYW
2 stops19h 42mMultiple Airlines
Sun 11/28:55 amEYW - ISP
1 stop11h 47mMultiple Airlines
Deal found 9/11$426
This KAYAK deal was found by Cheapflights users on 9/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2611:40 amISP - EYW
2 stops21h 37mBreeze Airways
Wed 10/2910:47 amEYW - ISP
2 stops24h 13mBreeze Airways
Deal found 9/9$583
This KAYAK deal was found by Cheapflights users on 9/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:40 amISP - EYW
2 stops21h 37mBreeze Airways
Sun 12/148:55 amEYW - ISP
2 stops28h 50mBreeze Airways
Deal found 9/11$653
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Tue 9/234:33 pmISP - EYW
2 stops43h 06mMultiple Airlines
Sun 9/288:55 amEYW - ISP
1 stop25h 45mMultiple Airlines
Deal found 9/11$726
This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:45 pmISP - EYW
2 stops37h 46mBreeze Airways
Sat 10/1110:47 amEYW - ISP
2 stops24h 13mBreeze Airways
Deal found 9/10$746
This Gotogate deal was found by Cheapflights users on 9/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:25 pmISP - EYW
2 stops42h 50mBreeze Airways
Sun 11/210:59 amEYW - ISP
3 stops33h 08mBreeze Airways
Deal found 9/11$755
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/247:30 amISP - EYW
2 stops28h 09mMultiple Airlines
Mon 9/298:47 amEYW - ISP
1 stop25h 53mMultiple Airlines
Deal found 9/11$756

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Key West 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 September 11, 2025.
Use the filters below to find and compare flights from Islip to Key West that are best for you.

Fly from

Islip

Fly to

Key West

Route

Depart

Return

Price

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 10/31

2:25 pm-10:07 am

2 stops19h 42m

Key West

Sun 11/2

8:55 am-8:42 pm

1 stop11h 47m

$426

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 10/26

11:40 am-9:17 am

2 stops21h 37m

Key West

Wed 10/29

10:47 am-11:00 am

2 stops24h 13m

$583

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 12/11

11:40 am-9:17 am

2 stops21h 37m

Key West

Sun 12/14

8:55 am-1:45 pm

2 stops28h 50m

$653

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Tue 9/23

4:33 pm-11:39 am

2 stops43h 06m

Key West

Sun 9/28

8:55 am-10:40 am

1 stop25h 45m

$726

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 10/4

8:45 pm-10:31 am

2 stops37h 46m

Key West

Sat 10/11

10:47 am-11:00 am

2 stops24h 13m

$746

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 10/31

2:25 pm-9:15 am

2 stops42h 50m

Key West

Sun 11/2

10:59 am-8:07 pm

3 stops33h 08m

$755

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Wed 9/24

7:30 am-11:39 am

2 stops28h 09m

Key West

Mon 9/29

8:47 am-10:40 am

1 stop25h 53m

$756

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 10/11

8:45 pm-10:31 am

2 stops37h 46m

Key West

Fri 10/17

9:57 am-8:07 pm

2 stops10h 10m

$798

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Best time to book a flight from Islip to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West 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 Key West

What is the cheapest month to book a flight from Islip to Key West?

Currently, August is the cheapest month in which you can book a flight from Islip to Key West (average of $328). Flying from Islip to Key West in March is currently the most expensive (average of $491). 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 Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Islip to Key West?

    There are many flights that can get you from Islip to Key West in 21h 37m. Fly via Breeze Airways to get the fastest option. The distance between Islip and Key West is about 1227 mi.

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

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

  • How can I find direct flights from Islip to Key West?

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

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

    Yes. Cheapflights offers flight deals from Islip to Key West 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 to Key West?

    Currently, August is the cheapest month in which you can book a flight from Islip to Key West (average of $328). Flying from Islip to Key West in March is currently the most expensive (average of $491). 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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