$119 Find Cheap Flights from Massachusetts to Oregon

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Low seasonJanuary
Cheapest flight$119
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Boston to Portland

FAQs for booking flights from Massachusetts to Oregon

  • How does KAYAK find such low prices on flights from Massachusetts 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 Massachusetts to Oregon.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Oregon?

    Alaska Airlines connects Massachusetts to Oregon with 18 flights per week. Hawaiian Airlines also offers 18 flights per week, while Qatar Airways follows with 18 flights per week.

  • How many airports are there in Oregon?

    There are 6 airports in Oregon. The busiest airport is Portland Airport (PDX), with 76% of all flights arriving there.

  • Which is the cheapest airport to fly into in Oregon?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Oregon is Portland Airport (PDX), with an average flight price of $295.

  • What is the cheapest day to fly to Oregon?

    Based on KAYAK data, the cheapest day to fly to Oregon is Wednesday where round-trip tickets can be as cheap as $371. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $446 on average.

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

    The cheapest time of day to fly to Oregon is generally in the afternoon, when round-trip flights cost $371 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Oregon is generally at night, which is peak travel time and where the average cost of a ticket is $451.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Massachusetts found in the last 72 hours was to Portland, at $337 round-trip. The most popular route is Boston (BOS) to Portland (PDX) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $337.

  • What is the cheapest month to fly from Massachusetts to Oregon?

    The cheapest month for flights from Massachusetts to Oregon is September, when tickets cost $438 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $699 and $652 respectively.

  • How far in advance should I book a flight from Massachusetts to Oregon?

    To get a below average price on the flight from Massachusetts to Oregon, you should book around 3 weeks before departure, which saves you about 44% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

  • How many cities have direct flights to Oregon?

    From Massachusetts, there are direct flights to Oregon from 1 city. This city is Boston and there are 58 direct flights each week.

  • How many direct flights to Oregon are there each day?

    There are around 9 direct flights from within Massachusetts to Oregon every day. Most flights (57%) depart in the morning.

  • How many direct flights to Oregon are there each week?

    Each week there are around 58 direct flights from within Massachusetts to Oregon. The most common day for departures is Friday, with 21% of flights taking off on this day.

  • How long is the flight to Oregon?

    An average nonstop flight from Massachusetts to Oregon takes 10h 38m, covering a distance of 2461 miles. The shortest route is Boston (BOS) to Portland (PDX) with an average flight time of 6h 20m.

  • How many long-haul flights are there to Oregon each week?

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Oregon. Instead, there are 58 medium-haul flights (3-6 hour flight duration), with the most arriving from Boston.

  • What are the most popular destinations in Oregon?

    Based on KAYAK flight searches, the most popular destination is Boise (46% of total searches to Oregon). The next most popular destinations are Eugene (22%) and Redmond (18%). Searches for flights to Medford (8%) and to North Bend (6%) are also popular.

Reviews of the top 5 airlines serving from Massachusetts to Oregon

 
Need help choosing which airline to fly with from Massachusetts 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
Alaska AirlinesOverall score based on 11095 reviews
7.1Food
8.1Boarding
7.0Entertainment
7.8Comfort
8.5Crew
Airline reviews

Terrible. My flight was pushed out three times finally the fourth time it was canceled completely. They sent me to a hotel that would not accept the voucher. And I had to pay for my cab and Uber . I arrived at the airport at five and didn’t get into my hotel until 1145.

2.0 MediocreAnonymous, Oct 2025LAX - RDM
Read more Alaska Airlines reviews

Terrible. My flight was pushed out three times finally the fourth time it was canceled completely. They sent me to a hotel that would not accept the voucher. And I had to pay for my cab and Uber . I arrived at the airport at five and didn’t get into my hotel until 1145.

Wouldve liked a meal option (that you didnt have to prepay for) for such a long flight. But otherwise staff was friendly and boarding/un boarding was as efficient as it could be

The flight attendants were friendly. I liked that I got a mini soda can, not just a small cup. No issues with our flight departure, etc.

5 hours delay, while seated moved passengers around on the plane. We were out on the runway, had to return to the gate. Changed tires.

The flight was great, unfortunately the Airport sucked at accommodating connection flight. My Mother had to sleep at the airport, making me feel helpless. Unable to determine if I should sleep or drive 3 hours each way to pick her up.

The crew was the best I’ve ever had HOWEVER when we arrived in Salt Lake City there were no Alaskan Airline employees to be found so we weren’t able to leave the plane until ANOTHER airline took pity on us. How could that possible happen?

Alaska is the best! I had my own row, complimentary wine, friendly flight attendants, free texting, and early arrival. Coach felt like 1st class. What more could I ask for?

The flight was good, but your car partner, Wisecars, was worse thane awful. They didn't have an agent nor had they inform me which car rental they were supposed to have issued a voucher.

Good. Night flight so tried to sleep most of the time. Very nice crew and smooth flight.

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

My flight was delayed three hours and then cancelled. The gate agent proceeded to rebook me in a middle seat without telling me and I was placed between two large individuals who did not fit in their own seats and instead took up most of mine. It was an awful experience.

The food options were limited and very specific. Some type of entertainment option for a 4.5 hour flight would have been nice.

Flight was smooth and comfortable. We were able to check a bag at counter due to full flight and boarded with an earlier group. We were there very early and didn’t hear the gate change just noticed our flight was no longer displayed st the gate. There were two other flights with gate shuffles - may be unavoidable but not desirable. First time I had to print my own luggage tag and attach at arrival. Not a fan of that process.

The crew was EXTREMELY helpful And sweet and the flight was smooth!

I received an email from Kayak with confirmation number for Hawaiian and another for Alaska. I received emails from Kayak for both my outbound and return flight to say "time to check in." Despite trying each number (Hawaiian and Alaska), I could not check in for outbound or return. It was then confusing at the airport - I hda "no place to go" to figure out how to check in. All the kiosks are marked "scan bag,etc." I wandered around with no agent to talk to. That was a bit stressful. Either Kayak, or airline, needed better communication on what to expect and to do.

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

When I purchased my ticket, it said i was flying with Hawaii airlines. Which is now operated by Alaska. Naturally I went to check in with Hawaii airlines once at the airport. However, there was no one at the desk until 7 am and their kiosk couldn’t find my tickets. I went over to Alaska and they said they couldn’t help me and to wait for Hawaii. My flight left at 7:15 so I didn’t have time to wait. They even told me to ask United which was next to the Hawaii desk what time Hawaii opened. I called the Hawaii airlines number and the operator told me to ask Alaska for help since my flight was operated by Alaska. So I went back and almost got brushed off again and sent to Hawaii. The Alaska desk attendant told me to check in at their kiosk but it didn’t work. I ran over to an older lady who was helping check bags and asked for help printing my boarding passes. Thankful she was able to do it right away! This whole debacle took a little over an hour. I wish there was better communication and knowledge between the two airlines because it could have been easily handled if everyone between the two airlines was on the same page. Once I ran through the airport to get to my gate, we were greeted with a smile and they seemed glad we made our flight! We were the last to board and barely made it. After the headache our flight was great! No complaints there.

Biggest issue: awfully narrow seats, + not a lot of leg room. Other than that, everything was good. Cabin crew seemed like very nice people.

The Kayak confirmation number did not work for checking in the day before. I checked in at 8.30 using my ticket number. When I arrived at the airport, I was informed that the flight was overbooked, and since I had checked in late, I did not have a seat. The Next flight was not until ten PM. I called my wife, who had been taking care of our kids all weekend, and she was upset, calling me a liar and telling me to stay in SD. It turned my weekend getaway into a nightmare! I blame the Kayak website and will not book flights using your app in the future.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

Flight was timely, relatively comfortable, with decent entertainment and food served. Only problem encountered was with the free messaging which I highly appreciate, but it did not work from iphone to non-iphones.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

The entertainment available didn’t work for anyone on the flight. Long 6 hr flight with no entertainment option and the staff didn’t know until an hour into the flight when we made sure they knew about it. They had no way to fix it.

Crew seemed a bit cranky. No seatback screens. But boarding was efficient and on time and we arrived early.

The worst landing I have ever had on a domestic flight. Thought we would lose the landing gear on landing in Newark. Then we spent 40 minutes trying to position the plane in the right place to be able to get the jet way to the plane. The plane arrived stopped. The announcer was that we were there. Everybody got up, then we were told to sit back down because they had to have us towed to a different position. We got towed and then everyone stood up and they told us we were in the wrong position to sit back down again, and then we got towed to a different position This did not happen immediately. It was 30 minutes while we wandered around a small section of the tarmac in Newark close to the gate, but apparently not close enough. Horrifying experience The CAB should be investigating that flight

Boarding was organized. Plane seats comfortable and service was attentive. Food options were good.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Everything you need to know for your flight to Oregon

Cabin class types available on flights to Massachusetts

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