HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$258+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PWM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 17, 2025.

Round-trip from

$711
(Delta)

One-way from

$258
(Delta)

Popular in

March

Cheapest in

January

Average price

$391
From Oakland to Portland
Search Deals
One-way flight from Oakland to Portland
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($140 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/16. 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 9/3012:37 pmOAK - PWM
2 stops32h 57mDelta
Fri 10/176:50 amPWM - OAK
2 stops41h 42mDelta
Deal found 9/16$711
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/312:37 pmOAK - PWM
2 stops32h 57mDelta
Fri 10/176:50 amPWM - OAK
2 stops41h 42mDelta
Deal found 9/16$717
This Southwest deal was found by Cheapflights users on 9/15. 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 10/1010:10 amOAK - PWM
2 stops10h 55mSouthwest
Mon 10/1311:45 amPWM - OAK
2 stops11h 15mSouthwest
Deal found 9/15$812
This Delta deal was found by Cheapflights users on 9/15. 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 9/2212:37 pmOAK - PWM
2 stops22h 24mDelta
Tue 9/305:00 pmPWM - OAK
2 stops9h 50mDelta
Deal found 9/15$901
This Delta deal was found by Cheapflights users on 9/15. 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 9/215:05 pmOAK - PWM
2 stops28h 29mDelta
Tue 9/306:35 amPWM - OAK
2 stops12h 49mDelta
Deal found 9/15$919
This Delta deal was found by Cheapflights users on 9/16. 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 12/175:45 amOAK - PWM
2 stops13h 32mDelta
Fri 1/21:03 pmPWM - OAK
2 stops13h 55mDelta
Deal found 9/16$938
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 12/185:45 amOAK - PWM
2 stops13h 32mDelta
Fri 1/21:03 pmPWM - OAK
2 stops13h 55mDelta
Deal found 9/16$1,809
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 12/195:45 amOAK - PWM
2 stops13h 32mDelta
Fri 1/21:03 pmPWM - OAK
2 stops13h 55mDelta
Deal found 9/16$1,859
This Delta deal was found by Cheapflights users on 9/16. 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 12/175:45 amOAK - PWM
2 stops13h 32mDelta
Sat 1/312:56 pmPWM - OAK
2 stops11h 49mDelta
Deal found 9/16$1,890
This Delta deal was found by Cheapflights users on 9/15. 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 10/115:55 amOAK - PWM
2 stops13h 24mDelta
Mon 10/132:38 pmPWM - OAK
2 stops12h 15mDelta
Deal found 9/15$1,999
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 12/185:45 amOAK - PWM
2 stops13h 32mDelta
Sat 1/312:56 pmPWM - OAK
2 stops11h 49mDelta
Deal found 9/16$2,761
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 12/195:45 amOAK - PWM
2 stops13h 32mDelta
Sat 1/31:03 pmPWM - OAK
2 stops11h 42mDelta
Deal found 9/16$2,811

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 September 17, 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

Thu 10/2

5:05 pm-12:34 am

2 stops52h 29m

Portland

Fri 10/17

6:50 am-9:32 pm

2 stops41h 42m

$711

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Wed 10/1

12:37 pm-12:34 am

2 stops32h 57m

Portland

Fri 10/17

6:50 am-9:32 pm

2 stops41h 42m

$711

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sat 10/4

6:00 am-12:34 am

2 stops39h 34m

Portland

Fri 10/17

6:50 am-9:32 pm

2 stops41h 42m

$711

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Tue 9/30

12:37 pm-12:34 am

2 stops32h 57m

Portland

Fri 10/17

6:50 am-9:32 pm

2 stops41h 42m

$711

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 10/3

12:37 pm-12:34 am

2 stops32h 57m

Portland

Fri 10/17

6:50 am-9:32 pm

2 stops41h 42m

$717

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 10/10

10:10 am-12:05 am

2 stops10h 55m

Portland

Mon 10/13

11:45 am-8:00 pm

2 stops11h 15m

$812

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Wed 12/17

5:45 am-10:17 pm

2 stops13h 32m

Portland

Fri 1/2

1:03 pm-11:58 pm

2 stops13h 55m

$938

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 12/18

5:45 am-10:17 pm

2 stops13h 32m

Portland

Fri 1/2

1:03 pm-11:58 pm

2 stops13h 55m

$1,809

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 12/19

5:45 am-10:17 pm

2 stops13h 32m

Portland

Fri 1/2

1:03 pm-11:58 pm

2 stops13h 55m

$1,859

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 12/18

5:45 am-10:17 pm

2 stops13h 32m

Portland

Sat 1/3

12:56 pm-9:45 pm

2 stops11h 49m

$2,761

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 23 results
1
2
3

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, January is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $296). Flying from Oakland, California to Portland, Maine in July is currently the most expensive (average of $394). 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated September 17, 2025.
Read reviews from past customers who have flown Southwest from Oakland to Portland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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 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 52h 29m. Delta provides one of the quickest options available for as low as $711. The distance between Oakland, California and Portland, Maine is about 2704 mi.

  • What is the cheapest airline to fly from Oakland, California to Portland, Maine round-trip?

    Cheapflights users have booked flights from Oakland, California to Portland, Maine round-trip from $449.

  • 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, January is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $296). Flying from Oakland, California to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to Boston flights
San Francisco to Boston flights
Ontario to Boston flights
San Diego to Boston flights
Santa Ana to Boston flights
Burbank to Boston flights
Las Vegas to Boston flights
San Jose to Boston flights
Sacramento to Boston flights
Oakland to Boston flights
Los Angeles to Portland flights
Long Beach to Boston flights
Reno to Boston flights
San Francisco to Portland flights
Fresno to Boston flights
Santa Barbara to Boston flights
Monterey to Boston flights
Los Angeles to Bangor flights
Palm Springs to Boston flights
San Luis Obispo to Boston flights
Medford to Boston flights
Santa Rosa to Boston flights
San Diego to Portland flights
Ontario to Portland flights
San Jose to Portland flights
San Francisco to Bangor flights
San Diego to Bangor flights
Sacramento to Portland flights
Santa Ana to Portland flights
Burbank to Portland flights
Las Vegas to Portland flights
San Luis Obispo to Portland flights
Reno to Portland flights
Arcata to Boston flights
Bakersfield to Boston flights
San Francisco to Bar Harbor flights
Palm Springs to Portland flights
San Jose to Bangor flights
San Francisco to Rockland flights
Sacramento to Bangor flights
Las Vegas to Bangor flights
Medford to Portland flights
San Francisco to Augusta flights
Las Vegas to Augusta flights
Los Angeles to Augusta flights
Santa Barbara to Portland flights
Fresno to Portland flights
Long Beach to Portland flights

Top airline flying from Oakland to Portland

Discover the top airline that operate flights from Oakland to Portland. 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$449Average$678FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.