$108 Find Cheap Flights from Oregon to Massachusetts

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Low seasonJanuary
Cheapest flight$108
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Portland to Boston

FAQs for booking flights from Oregon to Massachusetts

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

    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 Oregon to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oregon to Massachusetts 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 Oregon to Massachusetts?

    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 Oregon to Massachusetts 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 Oregon to Massachusetts?

    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 Oregon to Massachusetts 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 Massachusetts?

    Hawaiian Airlines connects Oregon to Massachusetts with 24 flights per week. Qatar Airways also offers 24 flights per week, while Alaska Airlines follows with 22 flights per week.

  • How many airports are there in Massachusetts?

    There are 8 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 91% of all flights arriving there.

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

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $249.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Wednesday where round-trip tickets can be as cheap as $343. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $455 on average.

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

    The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $262 on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $513.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Oregon found in the last 72 hours was to Boston, at $149 round-trip. The most popular route is Portland (PDX) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $149.

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

    The cheapest month for flights from Oregon to Massachusetts is February, when tickets cost $306 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $546 and $466 respectively.

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

    To get a below average price on the flight from Oregon to Massachusetts, you should book around 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

  • How many cities have direct flights to Massachusetts?

    From Oregon, there are direct flights to Massachusetts from 1 city. This city is Portland and there are 102 direct flights each week.

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

    There are around 15 direct flights from within Oregon to Massachusetts every day. Most flights (41%) depart in the morning.

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

    Each week there are around 102 direct flights from within Oregon to Massachusetts. The most common day for departures is Sunday, with 18% of flights taking off on this day.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Oregon to Massachusetts takes 10h 26m, covering a distance of 2442 miles. The shortest route is Portland (PDX) to Boston (BOS) with an average flight time of 5h 20m.

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

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Massachusetts. Instead, there are 102 medium-haul flights (3-6 hour flight duration), with the most arriving from Portland.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (88% of total searches to Massachusetts). The next most popular destinations are Hartford (11%) and Nantucket (1%). Searches for flights to West Tisbury (0%), to Hyannis (0%) and to Provincetown (0%) are also popular.

Reviews of the top 5 airlines serving from Oregon to Massachusetts

 
Need help choosing which airline to fly with from Oregon to Massachusetts? 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 10000 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.1Food
7.1Entertainment
Airline reviews

TERRIFIC! Thank you all. Jason Robert Kidwell My favorite flight attendants.

10.0 ExcellentJason, Jul 2025PDX - DCA
Read more Alaska Airlines reviews

TERRIFIC! Thank you all. Jason Robert Kidwell My favorite flight attendants.

I liked Alaska better than other carriers that I have EVER used. Unfortunately, the plane from LAX to Guanacaste leg of my journey had some mechanical problems and had to return to LAX - causing my journey to be very long and added a day to my total trip. The Airline was very prompt in offering their apology and have given me credit to use for my next flight. I thought the terminal in LAX was too cold for comfort, especially if there is a long wait between flights.

Not having to pay 160$ for a 20 lb and 12 lb bag that were clearly under 50 lbs and they overcharged me for them

Friendly staff, everything went smoothly. Gluten free snacks would would be the cherry on top!

We have always flown with Alaska when we can. As they have great customer service. This trip we had to transfer to Air LINGUS in Denver to go to Dublin. That’s where things went bad! Our checked luggage didn’t arrive. The process to make a claim was way more complicated than it should be. It took 5 days to recover our luggage. The whole time we couldn’t talk to a real person who could tell us anything. The whole time Alaska blamed Air lingus and vis a versa. No one seemed want to help us. That was the worst part.

I'm a platinum member with American Airlines, however, my ticket did not display status and thus I did not board with an early group. I traveled with my two daughters and we were given a row of seats that did not recline. Not the treatment I would have expected for a platinum customer. The flight was also a bit late leaving Portland. Also on my flight to Portland we were not given premium seats. In fact, we were in the last row of the aircraft.

I was at risk of not getting on the flight, as when I presented my boarding pass at the gate, it showed me as not having checked in. I was sent to the desk as the last of the other passengers boarded. The agent there said he could see that I had done all of my part and allowed times recommended, but it showed me as not checked in and he couldn't figure out how to correct it. He actually asked them to hold the flight as he struggled with it. He called for support, someone corrected it, and he printed boarding passes for both flights to reduce further issues. I did get on, and needed to ask someone to exit my seat.

We had a birthday one day off and almost missed the plane Our fault

5 hour delay from Portland to Newark. Boarded and then were told we had to get off and wait five hours for flight. No food vouchers or any other compensation because they said it was an air traffic control issue. Plane is bare minimum like a discount airline. They have free entertainment but you have to get to it on your own device no screens in the seats

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

Check-in process at SEA was very difficult, e.g., how to check-in and finding where to go to check-in. Staff that helped me was friendly. Security process very disorganized. Stopped at gate C2A to try to get on an earlier flight and four staff didn’t acknowledge me, some of the worst customer service I’ve experienced at a gate counter.

Flight got delayed and it was very inconvenient . Had to come with another carrier. Had to spend one more night in San Francisco.

Logging into next flight was an issue as I never received a confirmation code

Alaska airlines is not what I expected Very disappointed Unfriendly Discouraging Very bad customer service, heartbroken trying to explain to them my situation.

I could not check in ahead of time. Kayak did not give me a proper confirmation number to check in.

I loved flying Hawaiian Air! We didn’t pay to sit together, but we were able to anyway. They had usb charging ports and even outlets in some seats. They served a hot sandwich that was not very good, but we were still pleasantly surprised. The staff was very nice. The seats really made my booty hurt but maybe I’m just not used to sitting so long. Also, the AC was really cold even though I was wearing pants, a hoodie, and a light blanket.

A second drink service on a 6 hour flight would have been helpful.

The steward staff was particularly friendly and helpful. They smiled a lot and seemed anxious to be sure we enjoyed the flight.

Everything was good for the price I paid. Crew was very nice.

The worst flight experience I've ever had. Our flight was delayed 14 whole hours because the flight crew never showed up. We had to wait in a two hour line to get our new boarding passes, we were told we had no other option but to fly at 10pm (we didn't depart until 11:45pm). Everyone had to contact their hotels and car rental places, workplaces, etc. since we lost an entire day's worth of travel. The crew showed up at 10:15, which was past the time we were supposed to board. They were laughing and being completely smug when they boarded, and they took another hour to board us onto our flight. The flight crew never came to check in on us, we were quickly given one drink and sandwich and they turned off the lights and were negligent the rest of the trip. My mom asked three attendants for a seat belt extender, they never brought one. I was dehydrated and never received another drink. They were very rude and unfriendly, we had been up since 4am the morning of our flight and didn't land in our destination until 2am the next day (5am local time). This was unacceptable service and treatment, these flights are not cheap and we were inconvenienced out of an entire day of travel. This was 100% avoidable and was the fault of Hawaiian Airlines, and their crews inability to show up to work on time.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

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.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Oregon

Cabin classes available on flights to Oregon. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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