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Key West

$271+ Cheap flights from Islip, NY 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Jun 2 — Jun 91
Tue 6/2
Tue 6/9
1 adult, Economy
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Cheap 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 May 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sun 5/1711:12 am
ISP
-
EYW
1 stop24h 15m
Multiple Airlines
Thu 5/2112:05 pm
EYW
-
ISP
1 stop22h 00m
Multiple Airlines
Deal found 5/2$271
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/189:52 pm
ISP
-
EYW
1 stop16h 43m
Multiple Airlines
Sun 6/219:16 pm
EYW
-
ISP
1 stop23h 41m
Multiple Airlines
Deal found 4/29$285
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/1611:00 am
ISP
-
EYW
1 stop24h 25m
Multiple Airlines
Wed 5/2011:46 am
EYW
-
ISP
2 stops31h 27m
Multiple Airlines
Deal found 4/30$319
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sun 5/1011:12 am
ISP
-
EYW
1 stop24h 15m
Multiple Airlines
Thu 5/1412:05 pm
EYW
-
ISP
1 stop22h 00m
Multiple Airlines
Deal found 4/29$326
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sun 7/197:49 pm
ISP
-
EYW
2 stops16h 42m
Multiple Airlines
Fri 7/243:27 pm
EYW
-
ISP
1 stop18h 31m
Multiple Airlines
Deal found 4/29$377
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 6/198:43 pm
ISP
-
EYW
2 stops38h 42m
Multiple Airlines
Wed 6/2411:46 am
EYW
-
ISP
1 stop7h 19m
Multiple Airlines
Deal found 4/28$381
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/1311:00 am
ISP
-
EYW
1 stop24h 25m
Multiple Airlines
Sun 5/1712:05 pm
EYW
-
ISP
1 stop22h 00m
Multiple Airlines
Deal found 4/28$403
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sun 11/14:13 pm
ISP
-
EYW
1 stop18h 06m
Multiple Airlines
Fri 11/611:59 am
EYW
-
ISP
1 stop23h 21m
Multiple Airlines
Deal found 5/2$413
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/1411:12 am
ISP
-
EYW
1 stop24h 15m
Multiple Airlines
Mon 5/1812:07 pm
EYW
-
ISP
2 stops28h 40m
Multiple Airlines
Deal found 4/29$415

Find 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 May 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$271
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$486
Provider with most accurate pricing for Islip Long Island-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Islip Long Island-Key West flights.
Search Deals
From Islip Long Island to Key West
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 3, 2026.
Use the filters below to find and compare flights from Islip to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 5/17

11:12 am-11:27 am

1 stop24h 15m

Key West

Thu 5/21

12:05 pm-10:05 am

1 stop22h 00m

$271

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 5/16

11:00 am-11:25 am

1 stop24h 25m

Key West

Wed 5/20

11:46 am-7:13 pm

2 stops31h 27m

$319

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 10/15

10:57 am-11:19 am

1 stop24h 22m

Key West

Mon 10/19

10:59 am-11:20 am

2 stops48h 21m

$768

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 6/20

11:57 am-11:25 am

2 stops23h 28m

Key West

Tue 6/23

1:14 pm-5:29 pm

2 stops28h 15m

$777

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 6/19

8:43 pm-11:25 am

2 stops38h 42m

Key West

Mon 6/22

1:11 pm-1:28 pm

2 stops24h 17m

$780

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 7/11

11:57 am-10:24 am

2 stops22h 27m

Key West

Fri 7/24

11:07 am-11:17 am

1 stop24h 10m

$788

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 10/25

10:57 am-11:19 am

1 stop24h 22m

Key West

Sat 10/31

10:04 am-6:26 pm

2 stops32h 22m

$803
Quickest round-trip

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 6/4

5:50 pm-12:31 pm

2 stops18h 41m

Key West

Mon 6/8

1:11 pm-1:28 pm

2 stops24h 17m

$810

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 5/17

7:53 pm-12:34 pm

3 stops40h 41m

Key West

Thu 5/21

11:04 am-5:10 pm

2 stops6h 06m

$826

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 9/24

7:31 pm-9:24 am

2 stops37h 53m

Key West

Mon 9/28

12:59 pm-11:20 am

2 stops46h 21m

$833

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Sorted by cheapest first

Compare providers for flights from Islip to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Key West in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Islip, New York-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Islip, New York-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

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.

  • 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.

Browse thousands of different options on Cheapflights for your next trip

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