HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$234+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Islip to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$220
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$454
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. 0% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Mon 11/249:02 amISP - EYW
2 stops49h 47mMultiple Airlines
Fri 12/261:10 pmEYW - ISP
1 stop28h 45mMultiple Airlines
Deal found 10/28$283
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/124:58 pmISP - EYW
2 stops18h 22mMultiple Airlines
Sun 11/168:55 amEYW - ISP
1 stop25h 42mMultiple Airlines
Deal found 10/28$351
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 12/41:15 pmISP - EYW
1 stop20h 02mMultiple Airlines
Mon 12/811:19 amEYW - ISP
2 stops32h 15mMultiple Airlines
Deal found 10/28$398
This Booking.com deal was found by Cheapflights users on 10/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:40 amISP - EYW
2 stops21h 37mBreeze Airways
Mon 12/89:57 amEYW - ISP
2 stops10h 10mBreeze Airways
Deal found 10/28$764
This Gotogate deal was found by Cheapflights users on 10/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:21 pmISP - EYW
2 stops35h 54mBreeze Airways
Sun 11/168:55 amEYW - ISP
2 stops35h 12mBreeze Airways
Deal found 10/28$778
This Booking.com deal was found by Cheapflights users on 10/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:47 pmISP - EYW
2 stops34h 20mBreeze Airways
Fri 12/269:57 amEYW - ISP
2 stops10h 10mBreeze Airways
Deal found 10/28$880
This FlightHub deal was found by Cheapflights users on 10/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:47 pmISP - EYW
2 stops37h 32mBreeze Airways
Mon 12/89:57 amEYW - ISP
2 stops10h 10mBreeze Airways
Deal found 10/28$912
This United deal was found by Cheapflights users on 10/28. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/117:30 amISP - EYW
2 stops30h 34mMultiple Airlines
Tue 11/183:00 pmEYW - ISP
2 stops25h 15mMultiple Airlines
Deal found 10/28$1,056

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 October 29, 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

Thu 1/1

12:20 pm-12:30 pm

1 stop24h 10m

Key West

Sat 1/10

10:49 am-11:05 am

2 stops24h 16m

$234

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 1/4

11:40 am-12:30 pm

2 stops24h 50m

Key West

Sun 1/11

3:46 pm-2:39 pm

1 stop22h 53m

$236

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Mon 11/24

9:02 am-10:49 am

2 stops49h 47m

Key West

Fri 12/26

1:10 pm-5:55 pm

1 stop28h 45m

$283

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 12/4

1:15 pm-9:17 am

1 stop20h 02m

Key West

Mon 12/8

11:19 am-7:34 pm

2 stops32h 15m

$398

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 1/1

11:40 am-9:17 am

2 stops21h 37m

Key West

Sat 1/10

10:49 am-11:05 am

2 stops24h 16m

$554

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 1/4

11:40 am-9:17 am

2 stops21h 37m

Key West

Sun 1/11

9:46 am-1:21 pm

2 stops27h 35m

$599

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 12/4

11:40 am-9:17 am

2 stops21h 37m

Key West

Mon 12/8

9:57 am-8:07 pm

2 stops10h 10m

$764

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Wed 11/12

8:21 pm-8:15 am

2 stops35h 54m

Key West

Sun 11/16

8:55 am-8:07 pm

2 stops35h 12m

$778

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Mon 11/24

8:47 pm-7:07 am

2 stops34h 20m

Key West

Fri 12/26

9:57 am-8:07 pm

2 stops10h 10m

$880

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 12/5

8:47 pm-10:19 am

2 stops37h 32m

Key West

Mon 12/8

9:57 am-8:07 pm

2 stops10h 10m

$912

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Islip, New York-Key West flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $155). 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.

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

    Airlines like Breeze Airways fly from Islip, New York to Key West in about 21h 37m. The time it takes to get you to your destination can typically vary by up to . Islip, New York and Key West are separated by a distance of 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, 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 $155). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Islip to Key West

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Miami flights
Newark to Orlando flights
John F Kennedy Intl to Tampa flights
LaGuardia to Orlando flights
John F Kennedy Intl to West Palm Beach flights
Newark to Tampa flights
LaGuardia to Tampa flights
Newark to West Palm Beach flights
LaGuardia to West Palm Beach flights
Newark to Fort Myers flights
John F Kennedy Intl to Fort Myers flights
LaGuardia to Fort Myers flights
John F Kennedy Intl to Sarasota flights
Buffalo to Orlando flights
White Plains to Orlando flights
Newark to Sarasota flights
Syracuse to Orlando flights
LaGuardia to Jacksonville flights
John F Kennedy Intl to Jacksonville flights
Newark to Jacksonville flights
Buffalo to Fort Lauderdale flights
LaGuardia to Sarasota flights
Albany to Orlando flights
Newark to Key West flights
Islip to Orlando flights
Rochester to Orlando flights
Stewart to Fort Lauderdale flights
Islip to West Palm Beach flights
Stewart to Orlando flights
White Plains to Fort Lauderdale flights
White Plains to West Palm Beach flights
White Plains to Tampa flights
Islip to Fort Lauderdale flights
John F Kennedy Intl to Key West flights
White Plains to Miami flights
Buffalo to Tampa flights
LaGuardia to Key West flights
Newark to St Petersburg flights
Buffalo to Miami flights
Rochester to Fort Lauderdale flights
Islip to Fort Myers flights
Albany to Fort Lauderdale flights
Islip to Tampa flights
Newark to Orlando Sanford Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.