$124 Find Cheap Flights from Massachusetts to Oregon

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Low seasonJanuary
Cheapest flight$124
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 2% 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 14 flights per week. Qatar Airways also offers 14 flights per week, while Hawaiian Airlines follows with 13 flights per week.

  • How many airports are there in Oregon?

    There are 6 airports in Oregon. The busiest airport is Portland Airport (PDX), with 75% 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 $263.

  • 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 $363. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $457 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 2% 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 $474.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Massachusetts found in the last 72 hours was to Portland, at $297 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 $297.

  • 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 $800 and $738 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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 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 41 direct flights each week.

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

    There are around 6 direct flights from within Massachusetts to Oregon every day. Most flights (46%) depart in the morning.

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

    Each week there are around 41 direct flights from within Massachusetts to Oregon. The most common day for departures is Sunday, with 22% of flights taking off on this day.

  • How long is the flight to Oregon?

    An average nonstop flight from Massachusetts to Oregon takes 10h 47m, 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 41 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 (55% of total searches to Oregon). The next most popular destinations are Redmond (20%) and Eugene (13%). Searches for flights to Medford (10%) and to North Bend (2%) 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 11340 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.1Food
7.0Entertainment
Airline reviews

No accommodation or credit offered for cancelled layover flight to Eugene from portland

8.0 ExcellentDaren, Nov 2025BUR - PDX
Read more Alaska Airlines reviews

No accommodation or credit offered for cancelled layover flight to Eugene from portland

I've never flied them before but liked them. Weather was bad so a little scarey but they did a great job landing.

If they actually let me fly. I was rerouted to United and there was no Alaska airlines reps at all. Then the lady who worked the delta counter told me to go away and figure things out myself. Horrible experience.

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

Late. Too long a flight for a 737. 0.5 oz of pretzels for a 5+ hour flight at dinner time. One step above Ryan Air/ several below Delta.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

Flight delay caused me to miss my connecting flight home, but I was put up at a nearby motel, and it was great

My seat. The reprentative on the phone was bad. The passengers screamed at each other and no one stopped them. The directions boarding the plane were unclear. There was a medical incident and the ICU nurse present said the women was having a cardic incident. Cooler heads determined it was a UTI. I had a allergy attack and a guy got a mask from the flight attendent and told me to wear it. He "had kidney failure". Why didnt they tell him to wear the mask, why was he even on the plane? It was embarrassing, he said hurtful things. By the way, I have a degree in Medical Micrbiology from Northwestern Medical school. MT(ASCP). Look it up. I Know the difference between allergies and an infection. But we had to listen to the unstable screaming man.

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

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Alaska was fine as usual. My frustration came with accessing boarding passes. On the first trip, I could only get one to print ans took a picture of the second one. On our return trip, the system was down? Friends who booked directly with Alaska had theirs process. I even tried the 800 number and had others try it too. It said something in Spanish and hung up. The agent at the airport succeeded.

Delayed and cancelled flights were hard and very stressful, both ways!

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I had to cancel the flight because with a 3 hour delay for 'unexpected maintenance' in getting to LAX, I couldn't connect to an overseas flight that I had booked on Scandinavian Air.

The flight was CANCELED!!! Can’t get much more “poor” than that. I had to switch to American Airlines, add another layover and got home in Honolulu 4 hours later than I was supposed to be home. One bright spot was Josh with Alaska Airlines at SFO. He got me on a United Flight that got me home a few hours before I would have. Without him I would have gotten home almost 7 hours after my originally scheduled flight.

Canceled my flight within 24 hours, causing me arriving home midnight. Will never book Hawaiian airlines anymore

I like Hawaiian, it was great that they had good internet connection across the Pacific Ocean, thanks to Star Link satellites. The seating was comfortable, ( I was in economy ). Maybe I missed it, but I only got offered a beverage once. It was a nonstop flight KOA to SMF. I would take it again next time I go that way.

I always love flying Hawaii and I have nothing to add

Previously flown Hawaiian Airlines on similar routes, I found Alaska Airlines to be noticeably more comfortable. The seats on Alaska Airlines provided better support and cushioning, which made a significant difference on the long flight to the islands. When you’re spending 5-6 hours in the air, seat comfort really matters, and Alaska Airlines delivered where it counts. After comparing both carriers, I’ve decided to book with Alaska Airlines for all my future Hawaii trips. The superior seat comfort alone makes it worth choosing Alaska over Hawaiian Airlines. If you’re planning a trip to Hawaii and prioritizing comfort, I’d recommend giving Alaska Airlines a try. You won’t be disappointed. Highly recommended for Hawaii travel!

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Even though we were delayed, we were able to make our connection

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

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

Everything you need to know for your flight to Oregon

Cabin class types available on flights to Massachusetts

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