$99 Cheap Southwest Airlines flights San Diego (SAN) to Portland (PDX)

You’ll discover affordable round-trip Southwest Airlines flights from $202 from SAN to PDX by filtering your results from “Price (lowest to highest)” on Expedia. Or look for bargains from $99 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines flights to Portland are generally cheaper in the off-peak months of January and December. Whether you need a one-way or a return ticket, you could find a better deal then.

Start searching one to three months ahead of your departure date to score cheaper fares on Southwest Airlines flights from San Diego Intl. Airport (SAN) to Portland Intl. Airport (PDX). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Time it well, and you can enjoy significant savings on domestic flights.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

To see if there’s a direct trip from SAN to PDX with Southwest Airlines or other carriers, check the “Nonstop” filter when browsing for flights.

Search Southwest Airlines’s earliest flights from SAN to PDX by using the “Early Morning” and “Morning” filters. Not only will you get to your destination sooner, early departures also have a 20% less chance of being canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Jump on a Southwest Airlines flight from San Diego Intl. Airport (SAN) to Portland, and you’ll likely land at Portland Intl. Airport (PDX). This is the airline’s primary hub in this destination.

Changes are often free within 24 hours of booking, but your airline may charge a fee after that time. For further details about modifying your flights, check out your “Trips,” select your flight and click on “Manage Booking.” If you’d like the freedom to adjust your plans without additional charges, tick the “Changes included” and “No cancel fee” filters when organizing your next escape.