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$316+ 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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PNS
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Southwest deal was found by Cheapflights users on 12/13. 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.
Sun 12/288:25 amOAK - PNS
2 stops9h 25mSouthwest
Fri 1/26:10 pmPNS - OAK
1 stop7h 25mSouthwest
Deal found 12/13$692
This Southwest deal was found by Cheapflights users on 12/14. 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 12/275:25 amOAK - PNS
1 stop9h 10mSouthwest
Sun 1/46:10 pmPNS - OAK
1 stop7h 25mSouthwest
Deal found 12/14$753
This Delta deal was found by Cheapflights users on 12/14. 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 12/295:53 amOAK - PNS
2 stops8h 59mDelta
Fri 1/28:20 amPNS - OAK
2 stops9h 44mDelta
Deal found 12/14$1,498
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:53 amOAK - PNS
2 stops8h 52mDelta
Sun 12/286:00 amPNS - OAK
2 stops12h 04mDelta
Deal found 12/15$1,909
This Delta deal was found by Cheapflights users on 12/14. 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 12/225:53 amOAK - PNS
2 stops10h 38mDelta
Sun 1/411:05 amPNS - OAK
2 stops14h 53mDelta
Deal found 12/14$1,930
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:53 amOAK - PNS
2 stops10h 38mDelta
Sun 12/287:15 amPNS - OAK
2 stops10h 49mDelta
Deal found 12/15$2,029
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:53 amOAK - PNS
2 stops8h 52mDelta
Sun 12/2811:05 amPNS - OAK
2 stops14h 53mDelta
Deal found 12/15$4,003

Find 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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$442
(Southwest)

One-way from

$316
(Southwest)

Popular in

December

Cheapest in

April

Average price

$1,931
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
One-way flight from Oakland to Pensacola
Search Deals
Highest demand for flights based on searches. 40% potential increase in price ($378 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 38% potential price decrease ($154 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 15, 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

Tue 4/21

9:05 pm-9:30 am

2 stops10h 25m

Pensacola

Sun 4/26

5:40 am-10:20 am

1 stop6h 40m

$442

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Wed 6/10

7:30 am-6:05 pm

2 stops8h 35m

Pensacola

Thu 6/18

5:05 pm-11:45 pm

1 stop8h 40m

$464

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Mon 1/12

4:54 pm-9:11 am

2 stops14h 17m

Pensacola

Tue 1/20

6:00 am-4:14 pm

2 stops12h 14m

$556

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Sun 12/28

8:25 am-7:50 pm

2 stops9h 25m

Pensacola

Fri 1/2

1:55 pm-10:00 pm

2 stops10h 05m

$697

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Sat 12/27

5:25 am-4:35 pm

1 stop9h 10m

Pensacola

Sun 1/4

6:10 pm-11:35 pm

1 stop7h 25m

$753

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Mon 12/29

5:00 am-7:50 pm

1 stop12h 50m

$316

OaklandPensacola

OAK - PNS

OAKPNS

Oakland

Mon 12/29

6:31 pm-1:03 pm

3 stops40h 32m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

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 December.
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 Oakland, California-Pensacola flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Oakland, California-Pensacola flight deals on Cheapflights vs. eDreams >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 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 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, April is the cheapest month in which you can book a flight from Oakland, California to Pensacola (average of $142). Flying from Oakland, California to Pensacola in December is currently the most expensive (average of $379). 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 December 15, 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
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 10h 25m. Southwest provides one of the quickest options available for as low as $442. 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.. Southwest is 34% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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, April is the cheapest month in which you can book a flight from Oakland, California to Pensacola (average of $142). Flying from Oakland, California to Pensacola in December is currently the most expensive (average of $379). 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$361Average$462FlexibilityNo cancel feeOn-time63%

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