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Florida Keys

$109+ Cheap flights from Islip (ISP) to Florida Keys

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Islip to Florida Keys

Keep the following information in mind while searching for Islip to Florida Keys flight deals. Data was last updated August 20, 2025.

Round-trip from

$217
(Southwest)

One-way from

$109
(Southwest)

Popular in

December

Cheapest in

September

Average price

$257
From Islip Long Island to Florida Keys
Search Deals
One-way flight from Islip Long Island to Florida Keys
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Islip to Florida Keys

Cheapest flights from Islip to Florida Keys
Explore the most affordable flight options available from Islip to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:30 amISP - MIA
1 stop6h 35mSouthwest
Tue 9/305:05 pmMIA - ISP
1 stop5h 00mSouthwest
Deal found 8/19$217
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/164:00 pmISP - MIA
1 stop5h 15mSouthwest
Tue 9/237:10 amMIA - ISP
1 stop8h 00mSouthwest
Deal found 8/19$222
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/199:47 pmISP - MIA
2 stops18h 16mFrontier
Thu 10/239:51 amMIA - ISP
2 stops10h 51mFrontier
Deal found 8/18$226
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/209:49 amISP - MIA
2 stops14h 45mFrontier
Thu 10/239:51 amMIA - ISP
2 stops10h 51mFrontier
Deal found 8/18$228
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:25 pmISP - MIA
1 stop6h 40mSouthwest
Tue 11/1811:40 amMIA - ISP
2 stops10h 25mSouthwest
Deal found 8/17$232
This FlightHub deal was found by Cheapflights users on 8/18. 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 9/125:12 pmISP - MIA
2 stops23h 18mFrontier
Mon 9/156:00 amMIA - ISP
2 stops28h 40mFrontier
Deal found 8/18$233
This FlightHub deal was found by Cheapflights users on 8/18. 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.
Sat 9/275:05 pmISP - MIA
2 stops27h 16mFrontier
Sat 10/1110:00 amMIA - ISP
2 stops22h 59mFrontier
Deal found 8/18$236
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/273:40 pmISP - MIA
1 stop4h 55mSouthwest
Sat 10/116:00 amMIA - ISP
1 stop6h 10mSouthwest
Deal found 8/18$237
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:37 pmISP - MIA
2 stops15h 34mFrontier
Mon 11/1710:15 pmMIA - ISP
2 stops19h 27mFrontier
Deal found 8/17$240
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:54 amISP - MIA
2 stops14h 40mFrontier
Mon 11/1710:15 pmMIA - ISP
2 stops19h 27mFrontier
Deal found 8/17$243
This FlightHub deal was found by Cheapflights users on 8/17. 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.
Tue 9/26:05 amISP - MIA
2 stops32h 40mFrontier
Sun 9/76:00 amMIA - ISP
2 stops28h 40mFrontier
Deal found 8/17$247
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 8/287:33 pmISP - EYW
2 stops21h 18mMultiple Airlines
Fri 9/58:47 amEYW - ISP
1 stop26h 08mMultiple Airlines
Deal found 8/18$442

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Florida Keys 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 20, 2025.
Use the filters below to find and compare flights from Islip to Florida Keys that are best for you.

Fly from

Islip

Fly to

Florida Keys

Route

Depart

Return

Price

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Tue 9/23

5:30 am-12:05 pm

1 stop6h 35m

Miami

Tue 9/30

5:05 pm-10:05 pm

1 stop5h 00m

$217

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Tue 9/16

4:00 pm-9:15 pm

1 stop5h 15m

Miami

Tue 9/23

7:10 am-3:10 pm

1 stop8h 00m

$222

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sun 10/19

9:47 pm-10:34 am

2 stops12h 47m

Miami

Thu 10/23

9:51 am-8:42 pm

2 stops10h 51m

$226

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sun 10/19

9:47 pm-4:03 pm

2 stops18h 16m

Miami

Sat 10/25

5:47 pm-8:59 am

2 stops15h 12m

$226

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Thu 11/13

3:25 pm-10:05 pm

1 stop6h 40m

Miami

Tue 11/18

6:55 am-12:30 pm

1 stop5h 35m

$227

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Mon 10/20

9:49 am-12:34 am

2 stops14h 45m

Miami

Thu 10/23

9:51 am-8:42 pm

2 stops10h 51m

$228

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sun 10/26

11:40 am-8:07 am

2 stops20h 27m

Key West

Wed 10/29

9:47 am-11:00 am

2 stops25h 13m

$564

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 10/2

11:40 am-8:07 am

2 stops20h 27m

Key West

Sun 10/5

8:55 am-8:07 pm

2 stops35h 12m

$658

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 10/16

11:40 am-8:07 am

2 stops20h 27m

Key West

Sun 10/19

8:55 am-8:07 pm

2 stops35h 12m

$691

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Wed 9/17

8:21 pm-11:52 am

2 stops39h 31m

Key West

Wed 9/24

9:47 am-1:39 pm

2 stops27h 52m

$721

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 22 results
1
2
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Best time to book a flight from Islip to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys 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 Florida Keys

What is the cheapest month to book a flight from Islip to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Islip to Florida Keys (average of $328). Flying from Islip to Florida Keys in March is currently the most expensive (average of $492). 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.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated August 20, 2025.
Read reviews from past customers who have flown Southwest, Delta, and JetBlue from Islip to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
JetBlue
7.2
Good
2,916 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,039 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Islip to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Islip to Florida Keys?

    Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Florida Keys. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

  • How long is the flight from Islip to Florida Keys?

    There are many flights that can get you from Islip to Florida Keys in 6h 35m. Fly via Southwest, Frontier, or Breeze Airways to get the fastest option. There are 1114 mi between Islip and Florida Keys. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Islip to Florida Keys that include hotel bookings?

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

  • How can I find direct flights from Islip to Florida Keys?

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

  • Can I find deals for business class flights from Islip to Florida Keys?

    Yes. Cheapflights offers flight deals from Islip to Florida Keys 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 Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Islip to Florida Keys (average of $328). Flying from Islip to Florida Keys in March is currently the most expensive (average of $492). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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