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Key West

$280+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Sep 1 — Sep 81
Tue 9/1
Tue 9/8
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 August 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/31. 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 10/15:43 pm
ISP
-
EYW
1 stop14h 01m
Multiple Airlines
Sun 10/410:59 am
EYW
-
ISP
1 stop5h 59m
Multiple Airlines
Deal found 7/31$280
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Thu 9/37:09 pm
ISP
-
EYW
1 stop16h 18m
Multiple Airlines
Sun 9/612:05 pm
EYW
-
ISP
1 stop6h 09m
Multiple Airlines
Deal found 7/30$371
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/207:09 pm
ISP
-
EYW
1 stop16h 18m
Multiple Airlines
Mon 8/241:11 pm
EYW
-
ISP
2 stops27h 36m
Multiple Airlines
Deal found 8/1$381
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/1211:57 am
ISP
-
EYW
2 stops23h 28m
Multiple Airlines
Mon 8/1712:07 pm
EYW
-
ISP
1 stop21h 46m
Multiple Airlines
Deal found 7/28$390
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/207:09 pm
ISP
-
EYW
1 stop16h 18m
Multiple Airlines
Sun 8/237:53 pm
EYW
-
ISP
2 stops17h 35m
Multiple Airlines
Deal found 8/1$410
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 9/2511:52 am
ISP
-
EYW
2 stops21h 32m
Multiple Airlines
Mon 9/2810:59 am
EYW
-
ISP
1 stop5h 59m
Multiple Airlines
Deal found 7/28$416
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/1211:57 am
ISP
-
EYW
2 stops23h 28m
Multiple Airlines
Sun 8/1612:05 pm
EYW
-
ISP
1 stop21h 48m
Multiple Airlines
Deal found 7/28$423

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 August 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$280
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$494
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
High demand for flights, 1% potential price rise
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 August 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 August 2, 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

Thu 8/20

7:09 pm-11:27 am

1 stop16h 18m

Key West

Sun 8/23

7:53 pm-1:28 pm

2 stops17h 35m

$410

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 9/25

11:52 am-9:24 am

2 stops21h 32m

Key West

Mon 9/28

10:59 am-4:58 pm

1 stop5h 59m

$416

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 11/7

3:43 pm-10:19 am

1 stop18h 36m

Key West

Sat 11/14

10:04 am-5:33 pm

2 stops31h 29m

$423

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 9/3

10:57 am-10:27 am

2 stops23h 30m

Key West

Sun 9/6

12:05 pm-6:14 pm

1 stop6h 09m

$461

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Tue 9/1

2:08 pm-11:06 am

2 stops20h 58m

Key West

Mon 9/7

12:07 pm-9:53 am

1 stop21h 46m

$478
Quickest round-trip

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Mon 11/23

3:02 pm-10:24 am

2 stops19h 22m

Key West

Fri 11/27

10:59 am-7:06 pm

1 stop8h 07m

$562

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 1/9

9:40 am-11:26 am

1 stop25h 46m

Key West

Sat 1/16

12:19 pm-11:18 am

2 stops22h 59m

$614

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 9/25

9:39 am-9:24 am

2 stops23h 45m

Key West

Mon 9/28

10:59 am-12:58 pm

2 stops25h 59m

$699

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Wed 8/12

11:57 am-7:13 pm

2 stops31h 16m

Key West

Mon 8/17

1:11 pm-1:28 pm

2 stops24h 17m

$753
Cheapest one-way
Quickest one-way

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 8/13

5:50 pm-12:31 pm

2 stops18h 41m

$450

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 11 resultsSorted by cheapest first
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 August.
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.

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