Oakland

$285+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — OAK
Aug 3 — Aug 101
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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 July 29, 2025.

Round-trip from

$424
(Southwest)

One-way from

$285
(Mytrip)

Popular in

November

Cheapest in

September

Average price

$509
From Portland to Oakland
One-way flight from Portland to Oakland
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1010:30 amPWM - OAK
1 stop10h 10mSouthwest
Sun 9/145:50 amOAK - PWM
1 stop13h 35mSouthwest
Deal found 7/28$424
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3112:46 pmPWM - OAK
1 stop31h 11mSun Country Air
Thu 8/75:27 pmOAK - PWM
1 stop15h 24mSun Country Air
Deal found 7/27$575
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/103:21 pmPWM - OAK
3 stops35h 11mMultiple Airlines
Sun 9/146:00 amOAK - PWM
3 stops24h 06mMultiple Airlines
Deal found 7/28$664
This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 8/126:31 amPWM - OAK
2 stops12h 45mDelta
Sat 8/166:00 amOAK - PWM
2 stops8h 48mDelta
Deal found 7/28$1,850

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 29, 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 9/10

10:30 am-5:40 pm

1 stop10h 10m

Oakland

Sun 9/14

5:50 am-10:25 pm

1 stop13h 35m

$424

PortlandOakland

PWM - OAK

PWMOAK

Portland

Wed 9/10

3:21 pm-11:32 pm

3 stops35h 11m

Oakland

Sun 9/14

6:00 am-9:06 am

3 stops24h 06m

$664

PortlandOakland

PWM - OAK

PWMOAK

Portland

Tue 8/12

6:31 am-4:16 pm

2 stops12h 45m

Oakland

Sat 8/16

6:00 am-5:48 pm

2 stops8h 48m

$1,850

PortlandOakland

PWM - OAK

PWMOAK

Portland

Mon 12/15

6:05 pm-4:16 pm

3 stops25h 11m

$285

PortlandOakland

PWM - OAK

PWMOAK

Portland

Mon 12/15

12:50 pm-11:53 pm

2 stops14h 03m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, April is the cheapest month in which you can book a flight from Portland, Maine to Oakland, California (average of $183). Flying from Portland, Maine to Oakland, California in November is currently the most expensive (average of $259). 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 July 29, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta 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.

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
8.0
Very good

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.
  • 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, April is the cheapest month in which you can book a flight from Portland, Maine to Oakland, California (average of $183). Flying from Portland, Maine to Oakland, California in November is currently the most expensive (average of $259). 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$366Average$385FlexibilityNo cancel feeOn-time63%

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