$139 Find Cheap Flights from Oregon to Massachusetts

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Low seasonJanuary
Cheapest flight$139
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 7% increase in price.
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.

  • How many airports are there in Massachusetts?

    There are 6 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 96% 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 $201.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Saturday 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 $491 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 $337 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 $505.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Oregon found in the last 72 hours was to Boston, at $278 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 $278.

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

    The cheapest month for flights from Oregon to Massachusetts is August, when tickets cost $307 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $514 and $461 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 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 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 11 direct flights each week.

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

    There are around 2 direct flights from within Oregon to Massachusetts every day. All flights depart in the morning.

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

    Each week there are around 11 direct flights from within Oregon to Massachusetts. The most common day for departures is Monday, 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 8h 53m, covering a distance of 2442 miles. The shortest route is Portland (PDX) to Boston (BOS) with an average flight time of 5h 21m.

  • 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 11 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 (84% of total searches to Massachusetts). The next most popular destinations are Hartford (14%) and Nantucket (1%). Searches for flights to West Tisbury (1%), to New Bedford (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.
7.9
Alaska AirlinesOverall score based on 12319 reviews
8.5Crew
7.8Comfort
7.0Entertainment
7.1Food
8.1Boarding
Airline reviews

very nice blankets and comfortable seats. great service. Great flights.

10.0 ExcellentAnonymous, Apr 2026
PDX - SEA
Read more Alaska Airlines reviews

very nice blankets and comfortable seats. great service. Great flights.

great experience just at the end, we got in early and there wasn't anyone at the gate for 30 min so we had to just sit on the tarmac

Generally Good. Outbound flight was marred by a continuously s creaming baby. Fortunately the flight was only 90 mins long it would be nice if people traveling with small childres could be centered in one part of the plane. Also, you need to adapt your servey to include a "not applicable " option for things like food and entertainment, which are not offered on shorter flights. I fily Alaska by choice as given all the cirumstances, I fel\el you do a good job.

I was seating in 26A and the children in 27A and B were kicking me non-stop. They kicked me for hours nonstop and the parents refused to get off their phones or correct them. I kindly asked multiple times and got screamed at by the mom that her son is disabled. I told her I get it, but that I matter too and she is responsible for her child. He then kicked me so hard my drink spilled. Not one crew member or other passenger said or did a thing. It was so horrible.

My very first, first class flight! Loved the comfortable seats, foot rest and beverages. Did not have food due to short flight. Crew was very friendly!

Birding was slow. extremely slow; please do experiments on efficient plane boarding experiences; especially regarding passengers that pass their seat number…

This flight was all good. It was packed, but it took off on time and there were no problems. It would have been nice if they'd checked our bags for free, as they sometimes do.

Pretty smooth ride!… a little tight in the back and would’ve loved to had a movie screen… couldn’t beat the price to the West Coast!

I like not much people. Could tell the kids to be quiet.

I liked everything except, I left a brand new Switch 2 on the plane and talking to anybody about it is nearly impossible. I had to fill out a form and hope they get back to me in the next 2 weeks. I really hope they contact me. I saved for that thing for over a year and my son is heart broken.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Flight delayed two hours , missed connection flight then connection cancelled- horrible experience with hotel

Omg the disaster at the security was on another level! “Go to this end, sorry closed now, go to that end”. Ridiculous! This took over an hour! As far as the airline was concerned although I booked nearly a year ago I couldn’t get my bag tag - stand in another 15 minute line or my seat on Hawaiian Airlines- 5 more minutes! Then my TSA status was denied. Like what the heck! Makes a person not want to travel with this amount of incompetence

The Honolulu Hub needs 2 to 3 times the amount of things to do as well as shuttles that transport to/from gates and terminals. Arriving from OCONUS locations; transferring to CONUS locations its a miserable experience. Fetching and re-checking bags, then returning to a gate across the airport take longer than any other large airport. If youre confused by what I mean, the process goes like this: Disembark plane Walk a mile to the main terminal Walk half a mile to baggage claim Wait 40 minutes for baggage Walk a mile to re-check-in baggage Wait 20 minutes for checking in those bags Fo back through the wrong TSA line because the signage is poor Almost miss the connecting flight because your gate is across the airport.

The checking was disaster, the crew wasn't behave well. It took us two hours to check in, after that thr line at the TSA was long, we barely make the flight. Bad airline

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

The crew were exceptionally nice and accommodating. My wife was tired after the flight from Haneda, Tokyo. They let her sleep and served her dinner later after she woke up, before we landed in PDX.

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

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.