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$224+ Cheap flights from Islip, NY to Pensacola (ISP - PNS)

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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — PNS
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Islip to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Pensacola (PNS). 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

$224
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$408
Provider with most accurate pricing for Islip Long Island-Pensacola flight deals.
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Provider most trusted by Cheapflights users for Islip Long Island-Pensacola flights.
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From Islip Long Island to Pensacola
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Islip to Pensacola

Cheapest flights from Islip to Pensacola
Explore the most affordable flight options available from Islip to Pensacola. 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 10/27. 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 11/169:27 pmISP - PNS
1 stop13h 55mMultiple Airlines
Sun 11/238:16 pmPNS - ISP
2 stops37h 02mMultiple Airlines
Deal found 10/27$224
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 - PNS
1 stop18h 24mMultiple Airlines
Sun 11/1611:17 amPNS - ISP
1 stop22h 20mMultiple Airlines
Deal found 10/28$258
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/109:54 amISP - PNS
1 stop6h 01mMultiple Airlines
Mon 11/173:35 pmPNS - ISP
2 stops25h 07mMultiple Airlines
Deal found 10/29$321
This Southwest deal was found by Cheapflights users on 10/27. 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 12/75:50 amISP - PNS
2 stops11h 00mSouthwest
Thu 12/111:25 pmPNS - ISP
2 stops7h 40mSouthwest
Deal found 10/27$467
This Southwest deal was found by Cheapflights users on 10/27. 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 11/165:50 amISP - PNS
2 stops11h 00mSouthwest
Sun 11/2312:10 pmPNS - ISP
2 stops10h 40mSouthwest
Deal found 10/27$623
This Gotogate deal was found by Cheapflights users on 10/27. 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.
Sun 12/711:40 amISP - PNS
3 stops32h 34mBreeze Airways
Thu 12/111:14 pmPNS - ISP
2 stops29h 53mBreeze Airways
Deal found 10/27$779
This Booking.com deal was found by Cheapflights users on 10/27. 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 11/1611:40 amISP - PNS
2 stops28h 15mBreeze Airways
Sun 11/238:11 amPNS - ISP
3 stops28h 34mBreeze Airways
Deal found 10/27$788

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Pensacola 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 Pensacola that are best for you.

Fly from

Islip

Fly to

Pensacola

Route

Depart

Return

Price

IslipPensacola

ISP - PNS

ISPPNS

Islip Long Island

Sun 11/16

9:27 pm-10:22 am

1 stop13h 55m

Pensacola

Sun 11/23

8:16 pm-10:18 am

2 stops37h 02m

$224

IslipPensacola

ISP - PNS

ISPPNS

Islip Long Island

Wed 11/12

4:58 pm-10:22 am

1 stop18h 24m

Pensacola

Sun 11/16

11:17 am-10:37 am

1 stop22h 20m

$258

IslipPensacola

ISP - PNS

ISPPNS

Islip Long Island

Mon 11/10

9:54 am-2:55 pm

1 stop6h 01m

Pensacola

Mon 11/17

3:35 pm-5:42 pm

2 stops25h 07m

$321

IslipPensacola

ISP - PNS

ISPPNS

Islip Long Island

Tue 1/20

6:00 am-6:25 pm

2 stops13h 25m

Pensacola

Fri 1/30

7:50 am-4:15 pm

2 stops7h 25m

$383

IslipPensacola

ISP - PNS

ISPPNS

Islip Long Island

Sun 12/7

5:50 am-3:50 pm

2 stops11h 00m

Pensacola

Thu 12/11

1:25 pm-10:05 pm

2 stops7h 40m

$467

IslipPensacola

ISP - PNS

ISPPNS

Islip Long Island

Tue 11/25

9:09 pm-4:59 pm

1 stop20h 50m

Pensacola

Sun 11/30

1:44 pm-8:02 am

1 stop17h 18m

$560

IslipPensacola

ISP - PNS

ISPPNS

Islip Long Island

Sun 11/16

5:50 am-3:50 pm

2 stops11h 00m

Pensacola

Sun 11/23

12:10 pm-11:50 pm

2 stops10h 40m

$623

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Compare providers for flights from Islip to Pensacola

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 Pensacola in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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-Pensacola 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-Pensacola flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Islip, New York-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-Pensacola 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-Pensacola 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 Pensacola

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

What is the cheapest month to book a flight from Islip, New York to Pensacola?

Currently, March is the cheapest month in which you can book a flight from Islip, New York to Pensacola (average of $89). Flying from Islip, New York to Pensacola in April is currently the most expensive (average of $200). 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 Pensacola

Get insights into the airlines that provide service to Pensacola. 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 Pensacola. Reviews last updated October 29, 2025.
Peruse reviews from past customers who have flown with Southwest from Islip to Pensacola to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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 Pensacola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What is the cheapest airline to fly from Islip, New York to Pensacola round-trip?

    Our cheapest airline available from Islip, New York to Pensacola is Southwest. Our recent data shows that you can find tickets from as low as $338 on this airline.

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

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

  • How can I find direct flights from Islip to Pensacola?

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

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

    Yes. Cheapflights offers flight deals from Islip to Pensacola 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 Pensacola?

    Currently, March is the cheapest month in which you can book a flight from Islip, New York to Pensacola (average of $89). Flying from Islip, New York to Pensacola in April is currently the most expensive (average of $200). 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

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Gulf Breeze
Navarre
Foley
Perdido Key
Navarre Beach
Warrington

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Top airline flying from Islip to Pensacola

Discover the top airline that operate flights from Islip to Pensacola. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$338Average$493FlexibilityNo cancel feeOn-time63%

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