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$154+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — OAK
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$329
(Southwest)

One-way from

$154
(Delta)

Popular in

March

Cheapest in

September

Average price

$415
Provider with most accurate pricing for Portland-Oakland flight deals.
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Provider most trusted by Cheapflights users for Portland-Oakland flights.
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From Portland to Oakland
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One-way flight from Portland to Oakland
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Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 28, 2025.

This Southwest deal was found by Cheapflights users on 10/27. 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.
Fri 12/55:30 amPWM - OAK
2 stops12h 10mSouthwest
Wed 12/108:25 amOAK - PWM
2 stops10h 50mSouthwest
Deal found 10/27$379
This Southwest deal was found by Cheapflights users on 10/26. 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.
Mon 11/103:00 pmPWM - OAK
2 stops11h 20mSouthwest
Sun 11/1610:20 amOAK - PWM
2 stops11h 00mSouthwest
Deal found 10/26$458
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 12/2412:45 pmPWM - OAK
2 stops12h 35mSouthwest
Sat 12/277:45 pmOAK - PWM
2 stops12h 25mSouthwest
Deal found 10/27$607
This Southwest deal was found by Cheapflights users on 10/27. 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.
Tue 12/233:15 pmPWM - OAK
2 stops12h 05mSouthwest
Sat 12/277:45 pmOAK - PWM
2 stops12h 25mSouthwest
Deal found 10/27$638
This Delta deal was found by Cheapflights users on 10/28. 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 12/221:03 pmPWM - OAK
2 stops13h 55mDelta
Sun 12/285:53 amOAK - PWM
2 stops13h 50mDelta
Deal found 10/28$1,920
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:56 pmPWM - OAK
2 stops14h 02mDelta
Mon 12/295:53 amOAK - PWM
2 stops13h 50mDelta
Deal found 10/26$2,751
This Delta deal was found by Cheapflights users on 10/28. 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.
Sun 12/215:45 amPWM - OAK
2 stops13h 19mDelta
Mon 12/295:53 amOAK - PWM
2 stops13h 50mDelta
Deal found 10/28$2,791

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 October 28, 2025.
Use the filters below to find and compare flights from Portland to Oakland that are best for you.

Fly from

Portland

Fly to

Oakland

Route

Depart

Return

Price

PortlandOakland

PWM - OAK

PWMOAK

Portland

Wed 1/14

5:45 am-3:30 pm

2 stops12h 45m

Oakland

Wed 1/21

9:35 am-10:15 pm

2 stops9h 40m

$329

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 2/3

12:45 pm-9:25 pm

2 stops11h 40m

Oakland

Wed 2/11

9:20 am-10:15 pm

2 stops9h 55m

$358

PortlandOakland

PWM - OAK

PWMOAK

Portland

Wed 1/14

12:20 pm-10:53 pm

2 stops13h 33m

Oakland

Tue 1/20

4:54 pm-12:20 am

2 stops28h 26m

$362

PortlandOakland

PWM - OAK

PWMOAK

Portland

Fri 12/5

5:30 am-2:40 pm

2 stops12h 10m

Oakland

Wed 12/10

8:25 am-10:15 pm

2 stops10h 50m

$379

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 1/13

6:17 am-10:53 pm

2 stops19h 36m

Oakland

Tue 1/20

4:54 pm-12:20 am

2 stops28h 26m

$418

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 1/13

6:17 am-10:53 pm

2 stops19h 36m

Oakland

Wed 1/21

12:38 pm-12:20 am

2 stops32h 42m

$418

PortlandOakland

PWM - OAK

PWMOAK

Portland

Mon 11/10

3:00 pm-11:20 pm

2 stops11h 20m

Oakland

Sun 11/16

10:20 am-12:20 am

2 stops11h 00m

$458

PortlandOakland

PWM - OAK

PWMOAK

Portland

Sat 2/14

2:00 pm-10:45 pm

2 stops11h 45m

Oakland

Thu 2/19

7:55 am-10:45 pm

2 stops11h 50m

$477

PortlandOakland

PWM - OAK

PWMOAK

Portland

Wed 1/14

12:20 pm-10:53 pm

2 stops13h 33m

Oakland

Thu 1/22

5:55 am-12:20 am

2 stops15h 25m

$483

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 1/13

6:17 am-10:53 pm

2 stops19h 36m

Oakland

Sun 1/18

5:55 am-12:20 am

2 stops39h 25m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 24 results
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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 October.
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 Portland, Maine-Oakland, California flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Oakland, California flight deals on Cheapflights vs. eDreams >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 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 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.

Cheapflights Insights

Everything you need to know about your flight from Portland to Oakland

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

Currently, March is the cheapest month in which you can book a flight from Portland, Maine to Oakland, California (average of $98). Flying from Portland, Maine to Oakland, California in October is currently the most expensive (average of $178). 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 Oakland

Get insights into the airlines that provide service to Oakland. 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 Oakland. Reviews last updated October 28, 2025.
Peruse reviews from past customers who have flown with Southwest from Portland to Oakland to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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 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 12h 45m. Fly via Southwest or Delta to get the fastest option. Portland, Maine and Oakland, California are separated by a distance of 2704 mi. This flight may include one or multiple stops.

  • 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.

  • What is the cheapest month to book a flight from Portland, Maine to Oakland, California?

    Currently, March is the cheapest month in which you can book a flight from Portland, Maine to Oakland, California (average of $98). Flying from Portland, Maine to Oakland, California in October is currently the most expensive (average of $178). 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

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Top airline flying from Portland to Oakland

Discover the top airline that operate flights from Portland to Oakland. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$366Average$438FlexibilityNo cancel feeOn-time63%

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