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$140+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — PNS
Aug 17 — Aug 241
Mon 8/17
Mon 8/24
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 July 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/13. 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 9/55:01 pm
PWM
-
PNS
2 stops16h 00m
Breeze Airways
Wed 9/910:30 am
PNS
-
PWM
1 stop4h 54m
Breeze Airways
Deal found 7/13$323
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 9/511:07 am
PWM
-
PNS
1 stop29h 07m
Multiple Airlines
Wed 9/910:30 am
PNS
-
PWM
1 stop4h 54m
Multiple Airlines
Deal found 7/13$337
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Fri 10/309:48 am
PWM
-
PNS
1 stop27h 57m
Breeze Airways
Tue 11/38:48 am
PNS
-
PWM
1 stop23h 20m
Breeze Airways
Deal found 7/13$342
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/65:30 am
PWM
-
PNS
1 stop6h 07m
American Airlines
Mon 8/103:06 pm
PNS
-
PWM
1 stop7h 31m
American Airlines
Deal found 7/13$347
This Delta deal was found by Cheapflights users on 7/13. 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.
Sat 11/76:00 am
PWM
-
PNS
2 stops10h 05m
Delta
Tue 11/1012:00 pm
PNS
-
PWM
1 stop6h 29m
Delta
Deal found 7/13$352
This American Airlines deal was found by Cheapflights users on 7/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am
PWM
-
PNS
1 stop5h 29m
American Airlines
Wed 9/235:00 pm
PNS
-
PWM
1 stop5h 59m
American Airlines
Deal found 7/17$361
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Fri 10/309:48 am
PWM
-
PNS
1 stop7h 45m
Multiple Airlines
Tue 11/38:48 am
PNS
-
PWM
1 stop23h 20m
Multiple Airlines
Deal found 7/15$362
This United Airlines deal was found by Cheapflights users on 7/13. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:15 am
PWM
-
PNS
2 stops8h 54m
United Airlines
Thu 8/202:20 pm
PNS
-
PWM
1 stop6h 03m
United Airlines
Deal found 7/13$374
This United Airlines deal was found by Cheapflights users on 7/15. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 am
PWM
-
PNS
2 stops8h 37m
United Airlines
Tue 11/311:10 am
PNS
-
PWM
2 stops11h 13m
United Airlines
Deal found 7/15$376
This Delta deal was found by Cheapflights users on 7/13. 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.
Fri 10/306:00 am
PWM
-
PNS
2 stops7h 34m
Delta
Tue 11/31:39 pm
PNS
-
PWM
2 stops8h 27m
Delta
Deal found 7/13$384

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 July 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$323
(Kiwi.com)

One-way from

$140
(Kiwi.com)

Popular in

June

Cheapest in

October

Average price

$446
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. 14% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 18, 2026.
Use the filters below to find and compare flights from Portland to Pensacola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 10/29

6:00 am-12:34 pm

1 stop7h 34m

Pensacola

Tue 11/3

7:05 am-7:29 pm

2 stops11h 24m

$352

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Sat 11/7

6:00 am-12:34 pm

2 stops7h 34m

Pensacola

Tue 11/10

7:00 am-4:59 pm

2 stops8h 59m

$357

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 8/13

5:15 am-1:09 pm

2 stops8h 54m

Pensacola

Thu 8/20

2:20 pm-9:23 pm

1 stop6h 03m

$374

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 10/29

5:30 am-1:07 pm

2 stops8h 37m

Pensacola

Tue 11/3

11:10 am-11:23 pm

2 stops11h 13m

$376

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Wed 10/28

10:00 am-8:10 pm

2 stops11h 10m

Pensacola

Sun 11/1

1:39 pm-9:01 pm

1 stop6h 22m

$402

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 9/10

11:35 am-8:06 pm

2 stops9h 31m

Pensacola

Sun 9/13

6:00 am-1:05 pm

1 stop6h 05m

$429
Quickest round-trip

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Tue 9/1

6:00 am-1:09 pm

1 stop8h 09m

Pensacola

Wed 9/2

2:20 pm-9:23 pm

1 stop6h 03m

$437

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Sat 9/5

6:03 am-1:09 pm

1 stop8h 06m

Pensacola

Wed 9/9

9:00 am-11:32 pm

2 stops13h 32m

$442

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Thu 9/17

6:30 am-4:47 pm

2 stops11h 17m

Pensacola

Mon 9/21

5:52 pm-11:30 pm

1 stop4h 38m

$448

PortlandPensacola

PWM - PNS

PWMPNS

Portland

Sun 10/18

6:00 am-12:34 pm

1 stop7h 34m

Pensacola

Sat 10/24

11:58 am-12:10 am

2 stops11h 12m

$462

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

Showing 1-10 of 19 resultsSorted by cheapest first
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 July.
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, October is the cheapest month in which you can book a flight from Portland, Maine to Pensacola (average of $328). Flying from Portland, Maine to Pensacola in June is currently the most expensive (average of $708). 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.

How much does it cost to fly round-trip from Portland, Maine to Pensacola?

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 July 18, 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
7.8
Good
8,478 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Overall

7.8

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Delta
7.8
Good
8,478 reviews
Delta
7.8
Good
8,478 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Overall

7.8

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
American Airlines
7.1
Good
11,828 reviews
Delta
7.8
Good
8,478 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Overall

7.8

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.

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 $352, Delta can have you in Pensacola from Portland, Maine in 7h 34m. There are 1296 mi between Portland, Maine and Pensacola. This flight may include one or multiple stops.

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

    Delta, at $298, 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 39% 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, October is the cheapest month in which you can book a flight from Portland, Maine to Pensacola (average of $328). Flying from Portland, Maine to Pensacola in June is currently the most expensive (average of $708). 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

Browse thousands of different options on Cheapflights for your next trip

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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 July 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$298Average$462FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$328Average$455FlexibilityNo cancel feeOn-time71%

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