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$214+ Cheap flights from Oakland, CA to Portland, ME (OAK - PWM)

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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PWM
Mar 24 — Mar 311
Tue 3/24
Tue 3/31
1 adult, Economy
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Cheap 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 February 22, 2026.

This Southwest deal was found by Cheapflights users on 2/20. 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 4/111:55 pm
OAK
-
PWM
2 stops9h 00m
Southwest
Tue 4/76:10 am
PWM
-
OAK
2 stops10h 40m
Southwest
Deal found 2/20$397
This Southwest deal was found by Cheapflights users on 2/21. 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 5/138:20 am
OAK
-
PWM
2 stops11h 00m
Southwest
Thu 5/142:50 pm
PWM
-
OAK
2 stops12h 15m
Southwest
Deal found 2/21$408
This Southwest deal was found by Cheapflights users on 2/20. 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 4/19:25 am
OAK
-
PWM
2 stops10h 40m
Southwest
Thu 4/212:35 pm
PWM
-
OAK
2 stops13h 10m
Southwest
Deal found 2/20$473
This Southwest deal was found by Cheapflights users on 2/19. 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 3/69:30 am
OAK
-
PWM
2 stops11h 35m
Southwest
Tue 3/105:30 am
PWM
-
OAK
2 stops12h 35m
Southwest
Deal found 2/19$488
This Southwest deal was found by Cheapflights users on 2/19. 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 3/1310:00 am
OAK
-
PWM
2 stops11h 05m
Southwest
Mon 3/165:30 am
PWM
-
OAK
2 stops11h 10m
Southwest
Deal found 2/19$494
This Southwest deal was found by Cheapflights users on 2/21. 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 2/237:55 am
OAK
-
PWM
2 stops11h 50m
Southwest
Sat 2/282:00 pm
PWM
-
OAK
2 stops11h 45m
Southwest
Deal found 2/21$599
This Southwest deal was found by Cheapflights users on 2/18. 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 2/186:45 pm
OAK
-
PWM
2 stops14h 40m
Southwest
Tue 2/2412:45 pm
PWM
-
OAK
2 stops12h 30m
Southwest
Deal found 2/18$675
This Southwest deal was found by Cheapflights users on 2/21. 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.
Sun 2/228:10 pm
OAK
-
PWM
2 stops13h 15m
Southwest
Sun 3/12:25 pm
PWM
-
OAK
2 stops12h 45m
Southwest
Deal found 2/21$689
This Southwest deal was found by Cheapflights users on 2/19. 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 2/238:30 am
OAK
-
PWM
2 stops11h 15m
Southwest
Fri 2/272:25 pm
PWM
-
OAK
2 stops12h 45m
Southwest
Deal found 2/19$735
This Southwest deal was found by Cheapflights users on 2/20. 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 7/110:05 am
OAK
-
PWM
2 stops9h 50m
Southwest
Sun 7/56:45 am
PWM
-
OAK
1 stop8h 45m
Southwest
Deal found 2/20$827

Find 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 February 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$397
(Southwest)

One-way from

$214
(Southwest)

Popular in

December

Cheapest in

January

Average price

$377
Provider with most accurate pricing for Oakland-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Portland flights.
Search Deals
From Oakland to Portland
Search Deals
One-way flight from Oakland to Portland
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 22, 2026.
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

Wed 4/1

11:55 pm-11:55 am

2 stops9h 00m

Portland

Tue 4/7

6:10 am-1:50 pm

2 stops10h 40m

$397

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Wed 5/13

8:20 am-10:20 pm

2 stops11h 00m

Portland

Thu 5/14

2:50 pm-12:05 am

2 stops12h 15m

$408

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sat 3/7

9:20 am-12:10 am

2 stops11h 50m

Portland

Wed 3/11

12:30 pm-10:00 pm

2 stops12h 30m

$488

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 3/6

9:30 am-12:05 am

2 stops11h 35m

Portland

Tue 3/10

5:30 am-3:05 pm

2 stops12h 35m

$488

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 3/13

10:00 am-12:05 am

2 stops11h 05m

Portland

Mon 3/16

5:30 am-1:40 pm

2 stops11h 10m

$494

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sun 3/22

11:55 pm-2:15 pm

2 stops11h 20m

Portland

Sun 3/29

12:35 pm-9:05 pm

2 stops11h 30m

$833

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Wed 4/1

10:20 am-11:05 pm

2 stops9h 45m

$214

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 3/5

9:30 am-12:05 am

2 stops11h 35m

$229

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Mon 3/2

7:55 am-10:45 pm

2 stops11h 50m

$265

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sun 3/22

11:55 pm-2:15 pm

2 stops11h 20m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 16 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Portland, Maine flight deals on Cheapflights vs. FlightHub >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 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-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, December is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $118). Flying from Oakland, California to Portland, Maine in January is currently the most expensive (average of $189). 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 9h. Southwest provides one of the quickest options available for as low as $397. 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, December is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $118). Flying from Oakland, California to Portland, Maine in January is currently the most expensive (average of $189). 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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