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$249+ Cheap flights from Oakland, CA to Pensacola (OAK - 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PNS
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find flight deals from Oakland to Pensacola

Cheapest flights from Oakland to Pensacola
Explore the most affordable flight options available from Oakland to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

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.
Sat 11/155:45 amOAK - PNS
1 stop11h 35mSouthwest
Sat 11/225:20 pmPNS - OAK
2 stops9h 20mSouthwest
Deal found 10/12$388
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.
Thu 12/115:25 amOAK - PNS
2 stops11h 10mSouthwest
Mon 12/159:55 amPNS - OAK
1 stop12h 40mSouthwest
Deal found 10/12$434
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:00 amOAK - PNS
1 stop12h 50mSouthwest
Wed 12/311:25 pmPNS - OAK
2 stops10h 20mSouthwest
Deal found 10/13$510
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.
Fri 12/195:00 amOAK - PNS
1 stop6h 20mSouthwest
Sat 1/39:50 amPNS - OAK
2 stops10h 30mSouthwest
Deal found 10/11$544
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:30 amOAK - PNS
2 stops9h 20mSouthwest
Sat 12/273:30 pmPNS - OAK
1 stop8h 15mSouthwest
Deal found 10/13$642

Cheap flight deals from Oakland to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) 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 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$433
(Southwest)

Popular in

December

Cheapest in

October

Average price

$332
Provider with most accurate pricing for Oakland-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Pensacola flights.
Search Deals
From Oakland to Pensacola
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland 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 14, 2025.
Use the filters below to find and compare flights from Oakland to Pensacola that are best for you.

Fly from

Oakland

Fly to

Pensacola

Route

Depart

Return

Price

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Sat 11/15

5:45 am-7:20 pm

1 stop11h 35m

Pensacola

Sat 11/22

5:20 pm-12:40 am

2 stops9h 20m

$388

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Thu 12/11

5:45 am-6:35 pm

2 stops10h 50m

Pensacola

Mon 12/15

9:55 am-6:20 pm

2 stops10h 25m

$433

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Mon 12/22

5:00 am-7:50 pm

1 stop12h 50m

Pensacola

Wed 12/31

9:55 am-8:35 pm

1 stop12h 40m

$530

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Fri 12/19

5:00 am-1:20 pm

1 stop6h 20m

Pensacola

Sat 1/3

9:50 am-6:20 pm

2 stops10h 30m

$544

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Mon 12/22

8:30 am-7:50 pm

2 stops9h 20m

Pensacola

Sat 12/27

3:30 pm-9:45 pm

1 stop8h 15m

$642

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Tue 3/10

1:15 pm-8:47 am

2 stops17h 32m

Pensacola

Wed 3/11

1:59 pm-11:53 pm

2 stops11h 54m

$646

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Sat 1/3

5:15 am-6:00 pm

1 stop10h 45m

$249

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Sun 1/4

5:00 am-7:50 pm

1 stop12h 50m

$249

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Sun 1/4

6:10 am-1:03 pm

3 stops52h 53m

$594

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Sat 1/3

6:10 am-9:47 pm

3 stops37h 37m

$652

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/11

Showing 1-10 of 12 results
1
2

Compare providers for flights from Oakland 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 Oakland to Pensacola in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
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 Oakland, California-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-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 Oakland, California-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 Oakland to Pensacola

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

What is the cheapest month to book a flight from Oakland, California to Pensacola?

Currently, February is the cheapest month in which you can book a flight from Oakland, California to Pensacola (average of $160). Flying from Oakland, California to Pensacola in June is currently the most expensive (average of $288). 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 14, 2025.
Get a feel of what it's like to fly with Southwest from Oakland to Pensacola by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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 Oakland 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 Oakland, California to Pensacola?

    A quick flight from Oakland, California to Pensacola can take about 11h 35m. Southwest provides one of the quickest options available for as low as $388. The distance between Oakland, California and Pensacola is about 2052 mi.

  • What is the cheapest airline to fly from Oakland, California to Pensacola round-trip?

    Southwest, at $361, was found to be the cheapest airline from Oakland, California to Pensacola..

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland 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 Oakland, California to Pensacola?

    Currently, February is the cheapest month in which you can book a flight from Oakland, California to Pensacola (average of $160). Flying from Oakland, California to Pensacola in June is currently the most expensive (average of $288). 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 Oakland to Pensacola

Discover the top airline that operate flights from Oakland 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$361Average$462FlexibilityNo cancel feeOn-time63%

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