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Florida Keys

$102+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
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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 October 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/11. 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 11/84:58 pmISP - EYW
1 stop27h 48mMultiple Airlines
Sat 11/159:51 amEYW - ISP
2 stops25h 09mMultiple Airlines
Deal found 10/11$229
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/79:09 pmISP - MIA
2 stops14h 19mMultiple Airlines
Thu 12/1111:58 amMIA - ISP
1 stop25h 47mMultiple Airlines
Deal found 10/12$247
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/2711:40 amISP - EYW
2 stops21h 37mMultiple Airlines
Thu 12/48:55 amEYW - ISP
1 stop11h 19mMultiple Airlines
Deal found 10/12$282
This Southwest deal was found by Cheapflights users on 10/12. 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.
Sun 12/75:30 pmISP - MIA
1 stop5h 55mSouthwest
Thu 12/115:15 pmMIA - ISP
1 stop4h 25mSouthwest
Deal found 10/12$287
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/318:16 pmISP - MIA
2 stops21h 07mMultiple Airlines
Fri 1/912:39 pmMIA - ISP
1 stop22h 31mMultiple Airlines
Deal found 10/12$325
This Frontier deal was found by Cheapflights users on 10/12. 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 10/269:47 pmISP - MIA
2 stops16h 48mFrontier
Sun 11/29:45 pmMIA - ISP
2 stops12h 52mFrontier
Deal found 10/12$327
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Tue 12/2311:40 amISP - EYW
2 stops19h 27mMultiple Airlines
Sun 12/288:55 amEYW - ISP
1 stop24h 16mMultiple Airlines
Deal found 10/12$353
This Southwest deal was found by Cheapflights users on 10/10. 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 10/253:10 pmISP - MIA
1 stop5h 20mSouthwest
Thu 10/306:25 amMIA - ISP
1 stop5h 25mSouthwest
Deal found 10/10$357
This Frontier deal was found by Cheapflights users on 10/12. 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.
Sat 11/14:58 pmISP - MIA
2 stops19h 34mFrontier
Sun 11/26:37 pmMIA - ISP
2 stops16h 00mFrontier
Deal found 10/12$365
This Frontier deal was found by Cheapflights users on 10/12. 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
Sun 10/265:13 pmMIA - ISP
2 stops17h 24mFrontier
Deal found 10/12$375
This Southwest deal was found by Cheapflights users on 10/11. 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 11/86:00 amISP - MIA
1 stop8h 20mSouthwest
Sat 11/156:20 amMIA - ISP
1 stop5h 30mSouthwest
Deal found 10/11$377
This Southwest deal was found by Cheapflights users on 10/12. 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.
Fri 12/512:55 pmISP - MIA
2 stops7h 30mSouthwest
Mon 12/86:55 amMIA - ISP
2 stops8h 10mSouthwest
Deal found 10/12$382

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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$222
Provider with most accurate pricing for New York (NYC)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Miami flights.
Search Deals
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. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 13, 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

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 11/8

4:58 pm-8:46 pm

1 stop27h 48m

Key West

Sat 11/15

9:51 am-11:00 am

2 stops25h 09m

$229

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Thu 11/27

11:40 am-9:17 am

2 stops21h 37m

Key West

Thu 12/4

8:55 am-8:14 pm

1 stop11h 19m

$282

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sun 12/7

5:30 pm-11:25 pm

1 stop5h 55m

Miami

Thu 12/11

5:15 pm-9:40 pm

1 stop4h 25m

$287

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Wed 2/25

6:00 am-11:20 am

1 stop5h 20m

Miami

Wed 2/25

4:30 pm-9:55 pm

1 stop5h 25m

$287

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Wed 12/31

5:40 am-11:05 am

1 stop5h 25m

Miami

Fri 1/9

6:55 am-2:35 pm

1 stop7h 40m

$287

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sun 1/4

5:50 pm-10:55 pm

1 stop5h 05m

Miami

Sat 1/10

7:00 am-11:45 am

1 stop4h 45m

$337

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Tue 12/23

11:40 am-7:07 am

2 stops19h 27m

Key West

Sun 12/28

8:55 am-9:11 am

1 stop24h 16m

$353

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sat 10/25

3:10 pm-8:30 pm

1 stop5h 20m

Miami

Thu 10/30

5:15 pm-11:45 pm

2 stops6h 30m

$362

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Fri 12/5

12:55 pm-9:50 pm

2 stops8h 55m

Miami

Mon 12/8

7:10 am-12:15 pm

1 stop5h 05m

$377

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sat 11/8

6:00 am-2:20 pm

1 stop8h 20m

Miami

Sat 11/15

6:20 am-11:50 am

1 stop5h 30m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 28 results
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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, May is the cheapest month in which you can book a flight from Islip to Florida Keys (average of $155). Flying from Islip to Florida Keys 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.

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 October 13, 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
4,235 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,972 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,905 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,094 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,136 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 5h 55m. Fly via Southwest to get the fastest option. There are 1114 mi between Islip and Florida Keys.

  • 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, May is the cheapest month in which you can book a flight from Islip to Florida Keys (average of $155). Flying from Islip to Florida Keys 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

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