$59 Find Cheap Flights from San Jose to Oregon - Compare and Save

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Cheap Flights from San Jose to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Eugene
1h 35mNonstop
from $137per person
Portland
1h 45mNonstop
from $157per person
Boise
1h 35mNonstop
from $175per person
Redmond
3h 21m2 stops
from $203per person
Medford
3h 45m2 stops
from $233per person
Yakima
3h 53m2 stops
from $400per person
Pendleton
12h 20m4 stops
from $1,103per person
Booking Insights

KAYAK's insights & trends for San Jose to Oregon flights

Get data-powered insights and trends into flights from San Jose to Oregon to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from San Jose, California to Oregon?

Flight prices are below average for this route right now.

Flights to Oregon from San Jose, California usually cost between $222 and $656 in October.
The lowest price found in the past 5 days was $157 on Southwest (Oct 10-Oct 17).

What is the cheapest San Jose to Oregon flight route?

The cheapest ticket to Oregon from San Jose found in the last 5 days was to Portland, at $117 round-trip. The most popular route is from San Jose (SJC) to Portland (PDX), and the cheapest round-trip airline ticket found on this route in the last 5 days was $117.

What is the cheapest time of day to fly to Oregon?

The cheapest time of day to fly to Oregon is generally at night, when round-trip flights cost $311 on average. Morning departures are around 15% cheaper than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the evening, which is peak travel time and where the average cost of a ticket is $378.

Can I save money by flying with a layover from San Jose to Oregon?

No, with an average price for the route of $381, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Jose to Oregon?

The cheapest month for flights from San Jose to Oregon is January, when tickets cost $175 (return) on average. On the other hand, the most expensive months are March and September, when the average cost of round-trip tickets is $459 and $372 respectively.

What’s the cheapest day of the week to fly from San Jose to Oregon?

Your flight ticket price will generally be cheaper if you fly to Oregon on a Saturday and more expensive on a Monday. On your return trip to San Jose, you should consider flying back on a Saturday, and avoid Sundays for better deals.

How far in advance should I book a flight from San Jose to Oregon?

To get a below average price on the flight from San Jose to Oregon, you should book around 4 weeks before departure, which saves you about 60% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

January

Cheapest flight

$59
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from San Jose to Eugene

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from San Jose to Oregon?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Jose to Oregon.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Oregon?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose to Oregon is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Jose to Oregon?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from San Jose to Oregon with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Jose to Oregon?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from San Jose to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Oregon

  • Looking for a cheap flight? 25% of our users found tickets from San Jose to the following destinations at these prices or less: Portland $103 one-way - $248 round-trip

Reviews of the top 3 airlines serving from San Jose to Oregon

 
Need help choosing which airline to fly with from San Jose to Oregon? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4189 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

2.0 MediocreGlenn, Apr 2026
Read more Southwest reviews

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

It was as expected and I was grateful for the wheel chair help and ease of use.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Forget beverage, they didn't even have water for half the passangers?

Flight was not full! Had a whole row to myself.

Tight seats. Be prepared to sit in the middle if you are in boarding group C.

Wifi didn’t work, no service, seats are hard as rocks

This was a connecting flight for me and I had already traveled for 7 hours. First, the Pilot didn’t show up and then the gate changed twice, after which the flight was rescheduled for 2 hours later. This made me late and I had to make other transportation arrangements to get home to Astoria another 1 hour & 45 minutes away. This cost me $250 more than it should have. Will not fly southwest again.

The problem was going through San Diego, a trip that's become a new development.

No complimentary snacks or food. Had to buy drinks and food.

in-flight wifi was not working well. also the cabin temperature was a bit hot.

My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

These questions are hard to answer. It was not until I checked in that I learned my flight was going to Seattle for a connection and not Portland. I did not get notified, or asked, about this change by Alaska or Kayak. Thankfully I made this flight; but missed the connecting flight and it took me much longer to get home. A service representative for Alaska says this happens frequently with third party companies, like Kayak. Please please figure that out.

Alaska is always good. Happy polite employees, great airlines. I can’t say that about some of the others !

I would love to be awake for the announcements. I fell asleep because I was so tired. I know most people do not, and I just fell asleep. I did want some water, but that is ok. Not desperate. Thanks, I really make it a point to fly with this airline, since it is a very reliable and convenient way to fly. Thank you!

We didn’t have any entertainment, but it was a very short flight. We also sis to have any food except the free beverages and pretzels.

The flight attendants especially. Had 2 kids and the fun they had

Good and friendly staff. Nicely enjoyed the complimentary drink and snack.

All was good and they were able to seat my travel companion next to me. Thank you.

Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.

Check in process was a mess. Long lines, equipment malfuctioning. One line for baggage tags then a second line for bag checkin.

Despite two calls as well as a chat on the website, Alaska would not add my TSA number to my reservation. The flight was switched from Hawaiian to Alaska which caused them to mess this up in the first place

WiFi was not working thus the entertainment system did not work! Over 5 hours with nothing.

It was nice to have WiFi on board to steam on your device.

They canceled our scheduled flight. We flew back one day delayed. The company won't give us any compensation for the delay 😒.

Didn’t experience anything about it. You cancelled our flight 12 hours before our departure. Caused a major disruption with our vacation, and cost us much more money to travel, very disappointed. We’ll think twice about flying Hawaiian Airlines again.

Hawaiian cancelled my flight, told me I had been rebooked to an Alaskan Airlines flight the same day and then neglected to rebook me and my family. Thankfully, a member of Alaskan staff took care of me and made sure my family got to Hawai’i. It was a very rough morning.

More options for your flight from San Jose to Oregon

Complete your trip to Oregon with a hotel stay or car rental