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Key West

$127+ Cheap flights from Islip, NY to Key West (ISP - EYW)

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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/232:17 pm
ISP
-
EYW
1 stop22h 04m
Multiple Airlines
Mon 3/21:06 pm
EYW
-
ISP
2 stops46h 04m
Multiple Airlines
Deal found 1/26$244
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/228:33 am
ISP
-
EYW
1 stop27h 53m
Multiple Airlines
Sun 3/12:25 pm
EYW
-
ISP
2 stops17h 13m
Multiple Airlines
Deal found 1/25$266
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/259:33 am
ISP
-
EYW
1 stop23h 33m
Multiple Airlines
Mon 3/21:06 pm
EYW
-
ISP
2 stops46h 04m
Multiple Airlines
Deal found 1/25$298
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/85:08 pm
ISP
-
EYW
1 stop19h 18m
Multiple Airlines
Sun 3/159:46 am
EYW
-
ISP
2 stops27h 45m
Multiple Airlines
Deal found 1/25$416
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/125:08 pm
ISP
-
EYW
1 stop19h 18m
Multiple Airlines
Tue 3/171:01 pm
EYW
-
ISP
2 stops22h 09m
Multiple Airlines
Deal found 1/26$653
This Booking.com deal was found by Cheapflights users on 1/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:26 pm
ISP
-
EYW
2 stops17h 00m
Breeze Airways
Sun 3/159:46 am
EYW
-
ISP
2 stops27h 45m
Breeze Airways
Deal found 1/25$679
This Mytrip deal was found by Cheapflights users on 1/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:55 am
ISP
-
EYW
2 stops21h 14m
Breeze Airways
Tue 3/171:01 pm
EYW
-
ISP
2 stops22h 09m
Breeze Airways
Deal found 1/26$690
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 1/302:01 pm
ISP
-
EYW
2 stops20h 08m
Multiple Airlines
Sun 2/111:06 am
EYW
-
ISP
1 stop7h 52m
Multiple Airlines
Deal found 1/26$701

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$419
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
One-way flight from Islip Long Island to Key West
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 27, 2026.
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

Mon 2/23

2:17 pm-12:21 pm

1 stop22h 04m

Key West

Mon 3/2

1:06 pm-11:10 am

2 stops46h 04m

$244

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 2/22

8:33 am-12:26 pm

1 stop27h 53m

Key West

Sun 3/1

2:25 pm-7:38 am

2 stops17h 13m

$266

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Wed 2/25

9:33 am-9:06 am

1 stop23h 33m

Key West

Mon 3/2

1:06 pm-11:10 am

2 stops46h 04m

$298

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 3/8

5:08 pm-12:26 pm

1 stop19h 18m

Key West

Sun 3/15

9:46 am-1:31 pm

2 stops27h 45m

$416

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 3/12

5:08 pm-12:26 pm

1 stop19h 18m

Key West

Tue 3/17

1:01 pm-11:10 am

2 stops22h 09m

$653

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 3/8

7:26 pm-12:26 pm

2 stops17h 00m

Key West

Sun 3/15

9:46 am-1:31 pm

2 stops27h 45m

$679

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 3/12

11:55 am-9:09 am

2 stops21h 14m

Key West

Tue 3/17

1:01 pm-11:10 am

2 stops22h 09m

$690

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 2/22

11:55 am-9:09 am

2 stops21h 14m

Key West

Sun 3/1

9:46 am-1:31 pm

2 stops27h 45m

$734

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 3/6

2:31 pm-9:21 am

2 stops42h 50m

Key West

Mon 3/9

9:49 am-8:05 pm

2 stops10h 16m

$743

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Wed 7/22

6:09 pm-10:24 am

3 stops16h 15m

Key West

Sun 7/26

12:05 pm-8:03 pm

2 stops31h 58m

$773

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 12 results
1
2

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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.

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, New York to Key West?

Currently, May is the cheapest month in which you can book a flight from Islip, New York to Key West (average of $134). Flying from Islip, New York to Key West in August is currently the most expensive (average of $306). 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.

  • 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, New York to Key West?

    Currently, May is the cheapest month in which you can book a flight from Islip, New York to Key West (average of $134). Flying from Islip, New York to Key West in August is currently the most expensive (average of $306). 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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