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$385+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — OAK
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 septiembre 11, 2025.

Round-trip from

$618
(Delta)

One-way from

$385
(Southwest)

Popular in

November

Cheapest in

September

Average price

$331
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. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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.
sáb. 11/224:53 pmPWM - OAK
2 stops26h 18mDelta
mar. 12/24:54 pmOAK - PWM
2 stops20h 12mDelta
Deal found 9/10$618
This Southwest deal was found by Cheapflights users on 9/9. 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.
mié. 11/263:15 pmPWM - OAK
2 stops12h 10mSouthwest
sáb. 11/297:45 pmOAK - PWM
2 stops10h 55mSouthwest
Deal found 9/9$732
This Southwest deal was found by Cheapflights users on 9/10. 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.
mié. 11/263:15 pmPWM - OAK
2 stops11h 30mSouthwest
dom. 11/308:25 amOAK - PWM
2 stops12h 45mSouthwest
Deal found 9/10$828
This Southwest deal was found by Cheapflights users on 9/9. 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.
mar. 11/255:30 amPWM - OAK
2 stops16h 05mSouthwest
dom. 11/308:25 amOAK - PWM
2 stops12h 45mSouthwest
Deal found 9/9$844
This Delta deal was found by Cheapflights users on 9/9. 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.
sáb. 11/2212:48 pmPWM - OAK
2 stops11h 51mDelta
sáb. 11/295:45 amOAK - PWM
2 stops13h 29mDelta
Deal found 9/9$2,059
This Delta deal was found by Cheapflights users on 9/10. 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.
dom. 11/22:38 pmPWM - OAK
2 stops12h 15mDelta
mar. 11/45:55 amOAK - PWM
2 stops13h 24mDelta
Deal found 9/10$3,953

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 septiembre 11, 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

sáb. 11/22

4:53 pm-4:11 pm

2 stops26h 18m

Oakland

mar. 12/2

4:54 pm-4:06 pm

2 stops20h 12m

$618

PortlandOakland

PWM - OAK

PWMOAK

Portland

mar. 3/10

4:50 pm-11:53 pm

2 stops10h 03m

Oakland

mié. 3/11

1:15 pm-4:15 pm

2 stops24h 00m

$687

PortlandOakland

PWM - OAK

PWMOAK

Portland

mié. 11/26

3:15 pm-12:25 am

2 stops12h 10m

Oakland

sáb. 11/29

7:45 pm-9:40 am

2 stops10h 55m

$732

PortlandOakland

PWM - OAK

PWMOAK

Portland

mié. 11/26

3:15 pm-11:45 pm

2 stops11h 30m

Oakland

dom. 11/30

8:25 am-12:10 am

2 stops12h 45m

$828

PortlandOakland

PWM - OAK

PWMOAK

Portland

mar. 11/25

5:30 am-6:35 pm

2 stops16h 05m

Oakland

dom. 11/30

8:25 am-12:10 am

2 stops12h 45m

$844

PortlandOakland

PWM - OAK

PWMOAK

Portland

sáb. 11/22

1:25 pm-9:39 pm

2 stops11h 14m

Oakland

lun. 12/1

5:45 am-10:14 pm

2 stops13h 29m

$2,059

PortlandOakland

PWM - OAK

PWMOAK

Portland

sáb. 11/22

12:48 pm-9:39 pm

2 stops11h 51m

Oakland

sáb. 11/29

5:45 am-10:14 pm

2 stops13h 29m

$2,059

PortlandOakland

PWM - OAK

PWMOAK

Portland

dom. 11/2

2:38 pm-11:53 pm

2 stops12h 15m

Oakland

mar. 11/4

5:55 am-10:19 pm

2 stops13h 24m

$3,953

PortlandOakland

PWM - OAK

PWMOAK

Portland

jue. 10/9

11:45 am-8:00 pm

2 stops11h 15m

$385

PortlandOakland

PWM - OAK

PWMOAK

Portland

vie. 10/10

11:45 am-8:00 pm

2 stops11h 15m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 11 results
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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 septiembre 11, 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
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

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 10m. Fly via Delta or Southwest 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, 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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$366Average$385FlexibilityNo cancel feeOn-time63%

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