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$176+ Cheap flights from Portland, ME to Pensacola (PWM - PNS)

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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — PNS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Portland to Pensacola

Cheapest flights from Portland to Pensacola
Explore the most affordable flight options available from Portland to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
PWM
-
PNS
2 stops10h 23m
American Airlines
Tue 3/315:05 pm
PNS
-
PWM
1 stop5h 50m
American Airlines
Deal found 1/27$356
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
PWM
-
PNS
1 stop5h 09m
American Airlines
Mon 3/94:55 pm
PNS
-
PWM
1 stop6h 00m
American Airlines
Deal found 1/28$408
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1111:56 am
PWM
-
PNS
1 stop7h 16m
American Airlines
Fri 5/154:31 pm
PNS
-
PWM
1 stop5h 15m
American Airlines
Deal found 1/27$412
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:56 am
PWM
-
PNS
1 stop7h 16m
American Airlines
Mon 5/44:31 pm
PNS
-
PWM
1 stop5h 15m
American Airlines
Deal found 1/28$438
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:35 pm
PWM
-
PNS
2 stops9h 31m
Delta
Fri 5/156:00 am
PNS
-
PWM
1 stop5h 18m
Delta
Deal found 1/27$453
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/211:10 pm
PWM
-
PNS
2 stops9h 10m
Southwest
Tue 3/2410:05 am
PNS
-
PWM
2 stops12h 00m
Southwest
Deal found 1/28$458
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
PWM
-
PNS
1 stop5h 16m
American Airlines
Sun 5/34:31 pm
PNS
-
PWM
1 stop5h 15m
American Airlines
Deal found 1/27$462
This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 4/286:10 am
PWM
-
PNS
2 stops13h 50m
Southwest
Sun 5/31:35 pm
PNS
-
PWM
2 stops9h 30m
Southwest
Deal found 1/27$465
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 3/146:18 pm
PWM
-
PNS
1 stop14h 17m
Multiple Airlines
Fri 3/207:00 am
PNS
-
PWM
1 stop26h 17m
Multiple Airlines
Deal found 1/28$471

Find flight deals from Portland to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$348
(Kiwi.com)

One-way from

$176
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$384
Provider with most accurate pricing for Portland-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Pensacola flights.
Search Deals
From Portland to Pensacola
Search Deals
One-way flight from Portland to Pensacola
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 January 29, 2026.
Use the filters below to find and compare flights from Portland to Pensacola that are best for you.

Fly from

Portland

Fly to

Pensacola

Route

Depart

Return

Price

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Tue 3/3

6:00 am-3:23 pm

2 stops10h 23m

Pensacola

Tue 3/31

5:05 pm-11:55 pm

1 stop5h 50m

$356

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 3/5

6:00 am-10:09 am

1 stop5h 09m

Pensacola

Mon 3/9

4:55 pm-11:55 pm

1 stop6h 00m

$408

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 4/30

11:56 am-6:12 pm

1 stop7h 16m

Pensacola

Mon 5/4

4:31 pm-10:46 pm

1 stop5h 15m

$438

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Mon 5/11

2:35 pm-11:06 pm

2 stops9h 31m

Pensacola

Fri 5/15

6:00 am-12:18 pm

1 stop5h 18m

$453

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Sat 3/21

6:18 pm-7:35 am

1 stop14h 17m

Pensacola

Tue 3/24

7:00 am-10:17 am

1 stop26h 17m

$458

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Sat 3/21

1:10 pm-9:20 pm

2 stops9h 10m

Pensacola

Tue 3/24

10:05 am-11:05 pm

2 stops12h 00m

$458

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Tue 4/28

6:10 am-7:00 pm

2 stops13h 50m

Pensacola

Sun 5/3

1:35 pm-12:05 am

2 stops9h 30m

$465

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Wed 2/25

6:00 am-10:09 am

1 stop5h 09m

$176

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Tue 3/3

6:00 am-12:12 pm

1 stop7h 12m

$179

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 4/30

11:56 am-6:12 pm

1 stop7h 16m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 13 results
1
2

Compare providers for flights from Portland 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 Portland to Pensacola in January.
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 Portland, Maine-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Pensacola 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 Portland, Maine-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 Portland to Pensacola

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

What is the cheapest month to book a flight from Portland, Maine to Pensacola?

Currently, June is the cheapest month in which you can book a flight from Portland, Maine to Pensacola (average of $84). Flying from Portland, Maine to Pensacola in November is currently the most expensive (average of $238). 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 January 29, 2026.
Read reviews from past customers who have flown Delta and American Airlines from Portland to Pensacola. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,128 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,205 reviews
Delta
7.9
Good
8,128 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Portland to Pensacola. 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 Portland, Maine to Pensacola?

    For as low as $356, American Airlines can have you in Pensacola from Portland, Maine in 10h 23m. There are 1296 mi between Portland, Maine and Pensacola.

  • What are the cheapest airlines flying from Portland, Maine to Pensacola round-trip?

    Delta, at $312, was found to be the cheapest airline from Portland, Maine to Pensacola. An alternate airline flying to your destination would be American Airlines. You may be able to fly from Portland, Maine to Pensacola for 24% less than the average price by searching for these airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland 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 Portland, Maine to Pensacola?

    Currently, June is the cheapest month in which you can book a flight from Portland, Maine to Pensacola (average of $84). Flying from Portland, Maine to Pensacola in November is currently the most expensive (average of $238). 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
Navarre Beach
Perdido Key
Warrington

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Top 2 airlines flying from Portland to Pensacola

Discover the top 2 airlines that operate flights from Portland 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$312Average$430FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$316Average$450FlexibilityNo cancel feeOn-time71%

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