$305+ Cheap flights from Oakland, CA to Pensacola (OAK - 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PNS
Oct 14 — Oct 211
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Pensacola with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Oakland to Pensacola
Cheapest
Best
Last-minute
One-way
Cheapest flights from Oakland to PensacolaExplore 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 September 14, 2026.
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 September 14, 2026.
This Southwest deal was found by Cheapflights users on 9/11. 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 12/1111:55 am -
1 stop8h 00m
Mon 12/146:20 am -
1 stop7h 05m
Deal found 9/11![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/145:35 am -
2 stops7h 50m
Sat 10/172:15 pm -
1 stop7h 50m
Deal found 9/13![Southwest logo]()
$538
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 9/237:40 am -
2 stops10h 20m
Mon 9/282:10 pm -
1 stop7h 10m
Deal found 9/9![Southwest logo]()
$602
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 9/265:10 am -
2 stops9h 05m
Tue 9/297:00 am -
1 stop6h 30m
Deal found 9/13![Southwest logo]()
$622
This Southwest deal was found by Cheapflights users on 9/9. 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 9/2512:00 pm -
1 stop6h 05m
Tue 9/297:00 am -
1 stop6h 30m
Deal found 9/9![Southwest logo]()
$657
Best flights from Oakland to PensacolaDiscover carefully curated flight deals from Oakland to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
Discover carefully curated flight deals from Oakland to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
This Southwest deal was found by Cheapflights users on 9/11. 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 12/1111:55 am -
1 stop8h 00m
Mon 12/146:20 am -
1 stop7h 05m
Deal found 9/11![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/145:35 am -
2 stops7h 50m
Sat 10/172:15 pm -
1 stop7h 50m
Deal found 9/13![Southwest logo]()
$538
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 9/237:40 am -
2 stops10h 20m
Mon 9/282:10 pm -
1 stop7h 10m
Deal found 9/9![Southwest logo]()
$602
This Southwest deal was found by Cheapflights users on 9/13. 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 9/285:05 am -
2 stops8h 35m
Fri 10/25:30 am -
1 stop6h 40m
Deal found 9/13![Southwest logo]()
$622
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 9/299:30 am -
2 stops8h 30m
Sat 10/39:45 am -
1 stop8h 40m
Deal found 9/14![Southwest logo]()
$622
This Southwest deal was found by Cheapflights users on 9/9. 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 9/2512:00 pm -
1 stop6h 05m
Tue 9/297:00 am -
1 stop6h 30m
Deal found 9/9![Southwest logo]()
$657
Last-minute flights from Oakland to PensacolaDiscover last-minute flight deals from Oakland to Pensacola. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Pensacola. Data last updated September 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 9/237:40 am -
2 stops10h 20m
Mon 9/282:10 pm -
1 stop7h 10m
Deal found 9/9![Southwest logo]()
$602
This Southwest deal was found by Cheapflights users on 9/9. 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 9/2512:00 pm -
1 stop6h 05m
Tue 9/297:00 am -
1 stop6h 30m
Deal found 9/9![Southwest logo]()
$657
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 9/265:10 am -
2 stops9h 05m
Tue 9/297:00 am -
1 stop6h 30m
Deal found 9/13![Southwest logo]()
$622
This Southwest deal was found by Cheapflights users on 9/13. 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 9/287:00 am -
1 stop6h 40m
Fri 10/25:30 am -
1 stop6h 40m
Deal found 9/13![Southwest logo]()
$677
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/76:00 am -
2 stops10h 20m
Mon 10/125:15 pm -
2 stops9h 25m
Deal found 9/10![Southwest logo]()
$694
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/145:35 am -
2 stops7h 50m
Sat 10/172:15 pm -
1 stop7h 50m
Deal found 9/13![Southwest logo]()
$538
One-way flights from Oakland to PensacolaSearch for one-way flight options from Oakland to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
Search for one-way flight options from Oakland to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This Southwest deal was found by Cheapflights users on 9/11. 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.
Mon 10/126:00 am -
1 stop9h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Southwest logo]()
$305
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 September 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $460 (Southwest) |
One-way from | $305 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $468 |
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 7,457,451 searches. Data last updated September 14, 2026.
Use the filters below to find and compare flights from Oakland to Pensacola that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OaklandPensacola
OAK Oakland - PNS Pensacola
OAKPNS
Oakland
Mon 10/12
6:00 am-5:25 pm
1 stop9h 25m
Pensacola
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$305
OaklandPensacola
OAK Oakland - PNS Pensacola
OAKPNS
Oakland
Fri 12/11
11:55 am-9:55 pm
1 stop8h 00m
Pensacola
Mon 12/14
6:20 am-11:25 am
1 stop7h 05m
$460
OaklandPensacola
OAK Oakland - PNS Pensacola
OAKPNS
Oakland
Wed 10/14
5:35 am-3:25 pm
2 stops7h 50m
Pensacola
Sat 10/17
2:15 pm-8:05 pm
1 stop7h 50m
$538
OaklandPensacola
OAK Oakland - PNS Pensacola
OAKPNS
Oakland
Wed 9/23
7:40 am-8:00 pm
2 stops10h 20m
Pensacola
Mon 9/28
2:10 pm-7:20 pm
1 stop7h 10m
$602
OaklandPensacola
OAK Oakland - PNS Pensacola
OAKPNS
Oakland
Mon 9/28
5:05 am-3:40 pm
2 stops8h 35m
Pensacola
Fri 10/2
5:30 am-10:10 am
1 stop6h 40m
$622
OaklandPensacola
OAK Oakland - PNS Pensacola
OAKPNS
Oakland
Tue 9/29
9:30 am-8:00 pm
2 stops8h 30m
Pensacola
Sat 10/3
9:45 am-4:25 pm
1 stop8h 40m
$622
OaklandPensacola
OAK Oakland - PNS Pensacola
OAKPNS
Oakland
Fri 9/25
12:00 pm-8:05 pm
1 stop6h 05m
Pensacola
Tue 9/29
7:00 am-11:30 am
1 stop6h 30m
$657
Sorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
OAK-PNS
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.
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 September 14, 2026.
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.
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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.
Traveling to a place near Pensacola?
Book flights to Pensacola if you plan to visit one of these locationsNavarre
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Foley
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Navarre Beach
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Oakland and Pensacola flights
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Popular flight searches
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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 7,457,451 searches. Data last updated September 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$415 | Average$462 | FlexibilityNo cancel fee | On-time63% |