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$174+ Cheap flights from Portland, ME to Oakland, CA (PWM - OAK)

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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — OAK
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap flight deals from Portland to Oakland

Cheapest flights from Portland to Oakland
Explore the most affordable flight options available from Portland to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This Southwest deal was found by Cheapflights users on 7/23. 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 8/265:45 am
PWM
-
OAK
2 stops11h 10m
Southwest
Tue 9/17:40 am
OAK
-
PWM
2 stops10h 30m
Southwest
Deal found 7/23$311
This Southwest deal was found by Cheapflights users on 7/26. 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 8/255:45 am
PWM
-
OAK
2 stops11h 10m
Southwest
Tue 9/17:40 am
OAK
-
PWM
2 stops10h 30m
Southwest
Deal found 7/26$316
This Southwest deal was found by Cheapflights users on 7/23. 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 12/105:10 am
PWM
-
OAK
2 stops11h 55m
Southwest
Mon 12/147:55 am
OAK
-
PWM
2 stops10h 50m
Southwest
Deal found 7/23$409
This Southwest deal was found by Cheapflights users on 7/23. 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 10/136:00 pm
PWM
-
OAK
1 stop8h 15m
Southwest
Sun 10/187:35 pm
OAK
-
PWM
2 stops11h 15m
Southwest
Deal found 7/23$424
This Southwest deal was found by Cheapflights users on 7/25. 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 8/185:45 am
PWM
-
OAK
2 stops10h 25m
Southwest
Sat 8/227:20 am
OAK
-
PWM
2 stops10h 40m
Southwest
Deal found 7/25$480
This Southwest deal was found by Cheapflights users on 7/27. 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.
Thu 10/86:30 am
PWM
-
OAK
1 stop9h 15m
Southwest
Sun 10/117:35 pm
OAK
-
PWM
2 stops11h 15m
Southwest
Deal found 7/27$569

Find flight deals from Portland to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Oakland (OAK). 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 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(Southwest)

One-way from

$174
(Southwest)

Popular in

July

Cheapest in

January

Average price

$647
Provider with most accurate pricing for Portland-Oakland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Oakland flights.
Search Deals
From Portland to Oakland
Search Deals
One-way flight from Portland to Oakland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 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 Oakland 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 27, 2026.
Use the filters below to find and compare flights from Portland to Oakland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 8/25

5:45 am-1:55 pm

2 stops11h 10m

Oakland

Tue 9/1

7:40 am-9:10 pm

2 stops10h 30m

$316

PortlandOakland

PWM - OAK

PWMOAK

Portland

Thu 12/10

5:10 am-2:05 pm

2 stops11h 55m

Oakland

Mon 12/14

7:55 am-9:45 pm

2 stops10h 50m

$409

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 8/18

5:45 am-1:10 pm

2 stops10h 25m

Oakland

Sat 8/22

7:20 am-9:00 pm

2 stops10h 40m

$480

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 10/13

5:40 am-2:40 pm

2 stops12h 00m

Oakland

Sun 10/18

7:35 pm-9:50 am

2 stops11h 15m

$529

PortlandOakland

PWM - OAK

PWMOAK

Portland

Thu 10/8

5:20 am-12:40 pm

2 stops10h 20m

Oakland

Sun 10/11

7:35 pm-9:50 am

2 stops11h 15m

$574

PortlandOakland

PWM - OAK

PWMOAK

Portland

Sat 8/8

2:40 pm-11:55 pm

2 stops12h 15m

Oakland

Wed 8/12

9:30 am-10:05 pm

2 stops9h 35m

$794

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 8/18

2:53 pm-11:56 pm

2 stops12h 03m

Oakland

Sat 8/22

6:00 am-9:31 pm

2 stops12h 31m

$939
Quickest round-trip

PortlandOakland

PWM - OAK

PWMOAK

Portland

Fri 8/7

5:55 am-2:00 pm

2 stops11h 05m

Oakland

Tue 8/11

10:35 am-10:05 pm

1 stop8h 30m

$954
Cheapest one-way

PortlandOakland

PWM - OAK

PWMOAK

Portland

Thu 10/8

5:20 am-12:40 pm

2 stops10h 20m

$275
Quickest one-way

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 9/22

7:45 am-12:40 pm

1 stop7h 55m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 14 resultsSorted by cheapest first
1
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Compare providers for flights from Portland to Oakland

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 Oakland in July.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Oakland, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Oakland, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Oakland, California 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-Oakland, California 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 Oakland

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

Related info for your journey

Find useful and relevant information for your journey from Portland to Oakland. 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 Oakland, California?

    There are many flights that can get you from Portland, Maine to Oakland, California in 11h 10m. Fly via Southwest to get the fastest option. Portland, Maine and Oakland, California are separated by a distance of 2704 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Oakland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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