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$357+ Cheap flights from Oakland, CA to Portland, ME (OAK - PWM)

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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PWM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Oakland to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Portland (PWM). 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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$357
(Southwest)

Popular in

March

Cheapest in

January

Average price

$444
Provider with most accurate pricing for Oakland-Portland flight deals.
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Provider most trusted by Cheapflights users for Oakland-Portland flights.
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From Oakland to Portland
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($134 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 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 Oakland to Portland

Cheapest flights from Oakland to Portland
Explore the most affordable flight options available from Oakland to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 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.
Sat 12/137:15 pmOAK - PWM
2 stops12h 55mSouthwest
Tue 1/65:45 amPWM - OAK
2 stops11h 50mSouthwest
Deal found 10/27$357
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/268:30 amOAK - PWM
2 stops12h 35mSouthwest
Wed 12/3112:45 pmPWM - OAK
2 stops12h 35mSouthwest
Deal found 10/28$519
This Southwest deal was found by Cheapflights users on 10/30. 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 12/258:20 amOAK - PWM
2 stops10h 55mSouthwest
Sat 1/35:40 pmPWM - OAK
2 stops10h 50mSouthwest
Deal found 10/30$528
This Southwest deal was found by Cheapflights users on 10/30. 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 12/238:30 amOAK - PWM
2 stops12h 35mSouthwest
Sat 1/35:40 pmPWM - OAK
2 stops10h 50mSouthwest
Deal found 10/30$581
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:55 amOAK - PWM
2 stops13h 28mDelta
Tue 1/66:17 amPWM - OAK
2 stops12h 57mDelta
Deal found 10/27$628
This Southwest deal was found by Cheapflights users on 10/29. 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 11/119:40 amOAK - PWM
2 stops9h 35mSouthwest
Tue 11/2511:50 amPWM - OAK
2 stops9h 45mSouthwest
Deal found 10/29$635
This Delta deal was found by Cheapflights users on 10/30. 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 11/25:55 amOAK - PWM
2 stops13h 24mDelta
Mon 11/244:53 pmPWM - OAK
2 stops10h 10mDelta
Deal found 10/30$790
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:50 amOAK - PWM
1 stop8h 00mSouthwest
Fri 10/319:05 amPWM - OAK
2 stops11h 40mSouthwest
Deal found 10/28$854
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.
Wed 10/295:55 amOAK - PWM
2 stops13h 24mDelta
Fri 10/3112:45 pmPWM - OAK
2 stops11h 47mDelta
Deal found 10/28$859
This Delta deal was found by Cheapflights users on 10/30. 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 11/25:55 amOAK - PWM
2 stops13h 24mDelta
Tue 11/254:53 pmPWM - OAK
2 stops34h 10mDelta
Deal found 10/30$974

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Portland 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 30, 2025.
Use the filters below to find and compare flights from Oakland to Portland that are best for you.

Fly from

Oakland

Fly to

Portland

Route

Depart

Return

Price

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sat 12/13

7:15 pm-11:10 am

2 stops12h 55m

Portland

Tue 1/6

5:45 am-2:35 pm

2 stops11h 50m

$357

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 12/26

8:30 am-12:05 am

2 stops12h 35m

Portland

Wed 12/31

12:45 pm-10:20 pm

2 stops12h 35m

$519

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 12/25

8:20 am-10:15 pm

2 stops10h 55m

Portland

Sat 1/3

5:40 pm-1:30 am

2 stops10h 50m

$528

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Tue 12/23

8:30 am-12:05 am

2 stops12h 35m

Portland

Sat 1/3

5:40 pm-1:30 am

2 stops10h 50m

$581

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sat 12/13

5:55 am-10:23 pm

2 stops13h 28m

Portland

Tue 1/6

6:17 am-4:14 pm

2 stops12h 57m

$628

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Tue 11/11

9:40 am-10:15 pm

2 stops9h 35m

Portland

Tue 11/25

11:50 am-6:35 pm

2 stops9h 45m

$635

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Tue 3/31

1:15 pm-11:57 am

2 stops19h 42m

Portland

Wed 4/1

4:50 pm-11:53 pm

2 stops10h 03m

$677

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 12/25

6:10 am-10:36 am

3 stops49h 26m

$665

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 12/19

5:55 am-10:23 pm

2 stops13h 28m

$674

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 12/25

5:53 am-10:43 pm

2 stops13h 50m

$1,356

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 12 results
1
2

Compare providers for flights from Oakland to Portland

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 Portland 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 Oakland, California-Portland, Maine flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Oakland, California-Portland, Maine flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Oakland, California-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Portland, Maine 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-Portland, Maine 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 Portland

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

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

Currently, March is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $127). Flying from Oakland, California to Portland, Maine in December is currently the most expensive (average of $185). 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.

Related info for your journey

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

    A quick flight from Oakland, California to Portland, Maine can take about 12h 55m. Southwest provides one of the quickest options available for as low as $357. The distance between Oakland, California and Portland, Maine is about 2704 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Portland 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 Portland, Maine?

    Currently, March is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $127). Flying from Oakland, California to Portland, Maine in December is currently the most expensive (average of $185). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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