$259+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PWM
Nov 20 — Nov 271
Round-trip
1 adult, Economy
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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
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Last-minute
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Cheapest flights from Oakland to PortlandExplore 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 21, 2026.
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 21, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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.
Fri 12/49:10 am -
2 stops9h 40m
Mon 12/712:45 pm -
2 stops12h 20m
Deal found 10/20![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 10/17. 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 11/147:40 pm -
2 stops11h 50m
Sat 11/211:00 pm -
2 stops12h 45m
Deal found 10/17![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 10/17. 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 11/1310:00 am -
2 stops10h 55m
Sat 11/211:00 pm -
2 stops12h 45m
Deal found 10/17![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 10/17. 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 10/176:50 pm -
2 stops11h 50m
Sat 11/211:00 pm -
2 stops12h 45m
Deal found 10/17![Southwest logo]()
$517
This Southwest deal was found by Cheapflights users on 10/18. 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.
Mon 11/210:35 am -
2 stops10h 15m
Fri 11/65:20 am -
2 stops10h 55m
Deal found 10/18![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 10/18. 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.
Tue 11/177:55 am -
2 stops10h 55m
Fri 11/205:20 am -
2 stops10h 55m
Deal found 10/18![Southwest logo]()
$537
This Southwest deal was found by Cheapflights users on 10/17. 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 11/2410:25 am -
2 stops10h 30m
Mon 11/301:25 pm -
2 stops12h 05m
Deal found 10/17![Southwest logo]()
$778
Best flights from Oakland to PortlandDiscover carefully curated flight deals from Oakland to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
Discover carefully curated flight deals from Oakland to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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.
Fri 12/49:10 am -
2 stops9h 40m
Mon 12/712:45 pm -
2 stops12h 20m
Deal found 10/20![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/91:15 pm -
2 stops21h 38m
Wed 1/2012:50 pm -
2 stops14h 06m
Deal found 10/20![Delta logo]()
$542
This Southwest deal was found by Cheapflights users on 10/17. 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 11/147:40 pm -
2 stops11h 50m
Sat 11/211:00 pm -
2 stops12h 45m
Deal found 10/17![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 10/17. 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 11/1310:00 am -
2 stops10h 55m
Sat 11/211:00 pm -
2 stops12h 45m
Deal found 10/17![Southwest logo]()
$479
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/75:55 am -
2 stops13h 28m
Thu 1/2112:50 pm -
2 stops14h 06m
Deal found 10/20![Delta logo]()
$558
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/37:55 am -
2 stops10h 50m
Sat 11/75:25 am -
2 stops12h 55m
Deal found 10/19![Southwest logo]()
$517
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/65:05 pm -
2 stops27h 44m
Sun 1/1712:50 pm -
2 stops14h 06m
Deal found 10/20![Delta logo]()
$576
This Southwest deal was found by Cheapflights users on 10/18. 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.
Mon 11/210:35 am -
2 stops10h 15m
Fri 11/65:20 am -
2 stops10h 55m
Deal found 10/18![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/81:15 pm -
2 stops31h 34m
Sat 1/166:30 am -
2 stops20h 26m
Deal found 10/20![Delta logo]()
$639
This Southwest deal was found by Cheapflights users on 10/18. 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.
Tue 11/177:55 am -
2 stops10h 55m
Fri 11/205:20 am -
2 stops10h 55m
Deal found 10/18![Southwest logo]()
$537
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/312:34 pm -
2 stops30h 49m
Fri 1/222:35 pm -
2 stops12h 21m
Deal found 10/20![Delta logo]()
$717
This Southwest deal was found by Cheapflights users on 10/17. 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 11/2410:25 am -
2 stops10h 30m
Mon 11/301:25 pm -
2 stops12h 05m
Deal found 10/17![Southwest logo]()
$778
Last-minute flights from Oakland to PortlandDiscover last-minute flight deals from Oakland to Portland. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Portland. Data last updated October 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/18. 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.
Mon 11/210:35 am -
2 stops10h 15m
Fri 11/65:20 am -
2 stops10h 55m
Deal found 10/18![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/37:55 am -
2 stops10h 50m
Sat 11/75:25 am -
2 stops12h 55m
Deal found 10/19![Southwest logo]()
$517
This Southwest deal was found by Cheapflights users on 10/17. 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 11/1310:00 am -
2 stops10h 55m
Sat 11/211:00 pm -
2 stops12h 45m
Deal found 10/17![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 10/17. 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 11/147:40 pm -
2 stops11h 50m
Sat 11/211:00 pm -
2 stops12h 45m
Deal found 10/17![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 10/18. 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.
Tue 11/177:55 am -
2 stops10h 55m
Fri 11/205:20 am -
2 stops10h 55m
Deal found 10/18![Southwest logo]()
$537
This Southwest deal was found by Cheapflights users on 10/17. 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 11/2410:25 am -
2 stops10h 30m
Mon 11/301:25 pm -
2 stops12h 05m
Deal found 10/17![Southwest logo]()
$778
One-way flights from Oakland to PortlandSearch for one-way flight options from Oakland to Portland. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
Search for one-way flight options from Oakland to Portland. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This Delta deal was found by Cheapflights users on 10/16. 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 11/56:00 am -
2 stops12h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 3/1110:25 am -
2 stops10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 10/19. 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 12/79:10 am -
2 stops9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1110:58 pm -
3 stops33h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/283:52 pm -
3 stops38h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$664
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 October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $307 (Delta) |
One-way from | $259 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $556 |
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 7,457,451 searches. Data last updated October 21, 2026.
Use the filters below to find and compare flights from Oakland to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Thu 11/5
6:00 am-9:00 pm
2 stops12h 00m
Portland
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$259
Quickest round-trip
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Thu 3/11
10:25 am-12:10 am
2 stops10h 45m
Portland
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$299
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Fri 12/4
9:10 am-9:50 pm
2 stops9h 40m
Portland
Mon 12/7
12:45 pm-10:05 pm
2 stops12h 20m
$308
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Sat 11/14
7:40 pm-10:30 am
2 stops11h 50m
Portland
Sat 11/21
1:00 pm-10:45 pm
2 stops12h 45m
$461
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Fri 11/13
10:00 am-11:55 pm
2 stops10h 55m
Portland
Sat 11/21
1:00 pm-10:45 pm
2 stops12h 45m
$479
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Tue 11/3
7:55 am-9:45 pm
2 stops10h 50m
Portland
Sat 11/7
5:25 am-3:20 pm
2 stops12h 55m
$517
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Mon 11/2
10:35 am-11:50 pm
2 stops10h 15m
Portland
Fri 11/6
5:20 am-1:15 pm
2 stops10h 55m
$528
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Tue 11/17
7:55 am-9:50 pm
2 stops10h 55m
Portland
Fri 11/20
5:20 am-1:15 pm
2 stops10h 55m
$537
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Sat 1/9
1:15 pm-1:53 pm
2 stops21h 38m
Portland
Wed 1/20
12:50 pm-11:56 pm
2 stops14h 06m
$542
OaklandPortland
OAK Oakland - PWM Portland
OAKPWM
Oakland
Thu 1/7
5:55 am-10:23 pm
2 stops13h 28m
Portland
Thu 1/21
12:50 pm-11:56 pm
2 stops14h 06m
$558
Showing 1-10 of 15 resultsSorted by cheapest first
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.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
OAK-PWM
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.
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.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsLewiston
North Conway
Brunswick
Conway
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