$135 Find Cheap Flights from Massachusetts to Oregon

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Low seasonJanuary
Cheapest flight$135
Best time to beat the crowds with an average 8% 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.

  • 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 $212.

  • 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 $374. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $458 on average.

  • 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 $377 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $409.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Massachusetts found in the last 72 hours was to Portland, at $277 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 $277.

  • 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 $383 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $957 and $660 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 46% 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 28 direct flights each week.

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

    There are around 3 direct flights from within Massachusetts to Oregon every day. Most flights (70%) depart in the afternoon.

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

    Each week there are around 20 direct flights from within Massachusetts to Oregon. The most common day for departures is Monday, with 20% of flights taking off on this day.

  • How long is the flight to Oregon?

    An average nonstop flight from Massachusetts to Oregon takes 9h 00m, covering a distance of 2461 miles. The shortest route is Boston (BOS) to Portland (PDX) with an average flight time of 6h 02m.

  • 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 20 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 (41% of total searches to Oregon). The next most popular destinations are Medford (20%) and Eugene (16%). Searches for flights to Redmond (16%) 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.
7.9
Alaska AirlinesOverall score based on 12262 reviews
8.5Crew
7.0Entertainment
7.0Food
7.8Comfort
8.1Boarding
Airline reviews

Had to buy a snack box as I am gluten free. They should be free in extra comfort. Food they provided was awful. Not enough water stops.

10.0 ExcellentDoretta, Apr 2026
HNL - PDX
Read more Alaska Airlines reviews

Had to buy a snack box as I am gluten free. They should be free in extra comfort. Food they provided was awful. Not enough water stops.

Tight hot cramped seating. Gate change plus a board and de plane request with two hour delay

We treated ourselves to first class and were underwhelmed by the experience. No screen for entertainment. Food was not great...only one or two options, small portions, dry. We won't waste our money upgrading again. Good news was we made it to PDX safe and sound. Crew was attentive.

The flight would have been very good , if not dor the constantly screaming baby in the row behind me. Is there a way to isolate people traveling with infants? This is not the first time this has happened to me.

I was on flight #3022 departed from San Diego, California to Medford, Oregon. I had Denise & Damaris as my flight attendants. I didn’t have much interaction with Damaris, but I did with Denise who had, this calm, cool collective voice when she spoke about the emergency exit plans before takeoff. I travel often and I’ve never met a flight attendant that can put you at ease. I felt she respects and takes pride in her position and more airlines need to adopt the integrity and respect that she has for Alaska Airlines. Debbie

it was good except the too big men in my personal space.

We were on the ground for over 2hrs Flt scheduled to leave at 5:40pm, actual departure was at 9:00pm. Around 8:00pm we were offered an option to deplane,some did while others stayed.

My daughter has anxiety and became nauseous after boarding the plane and before take off. She went to the plane bathroom and ended up having to vomit, and your staff promptly removed us from the flight. We explained that it was due to my daughter’s anxiety, and that the condition would not continue in the air, but they removed us anyway. We have flown many many times before on many different airlines and my daughter’s anxiety has resulted in nausea and sickness before takeoff, and every airline has been accommodating and professional. This is was our first time flying with your airline, and also the first time we have ever been removed from a flight. This was the worst service we have ever experienced. This was a special surprise trip we gifted to my daughter for graduating college. I had also paid to upgrade the family to first class and sit all together which we had never done before and can’t afford on a normal basis. Our removal from the flight was not only extremely embarrassing, but devastating for my daughter. My daughter and I were removed from the plane and a call was made by your staff to medical personnel, a few questions were asked of my daughter, and then she was magically cleared. All of this took mere minutes. Why this could not have been performed while we were on the plane, or why this could not have been performed off the plane and then us allowed to reboard is beyond me. My wife and youngest daughter continued on the original flight alone and were very upset and crying due to the situation, yet the staff did nothing to console or assist them. My wife states that upon arrival in Portland and as they were exiting the plane, one of the stewardesses involved said “byyyyeeeee” to them sarcastically and laughed. Myself and my oldest daughter had to wait 4 hours for an alternate flight and were sat in regular seats because our first class seat purchase could not be honored. My wife wasn’t allowed to pick up our rental car and had to wait 4 hours with our luggage until I arrived. The delay prevented us from being able to carry out planned events and ruined the first day of our trip. Upon explaining all of this to your customer service, we received no sympathy, assistance, or compensation other than your staff submitting a request for a reimbursement of my and my daughters first class upgrade cost. When checking in early for our flight back home, the luggage cost for myself and my eldest daughter was no longer discounted as it was for my wife and youngest daughter. Customer service once again could not assist me over the phone and rectify what should have been a minor adjustment. Instead they stated I would have to wait until we physically checked bags in at the airport and then ask staff to adjust the luggage cost. With everything else we had experienced, I was not going to leave that to chance and instead paid full price for the luggage ahead of time. Or experience with Alaska Airlines was a complete disaster and I am baffled at the lack of empathy and assistance from your staff. I’m not sure of what else to say other than the fact that unless we are compensated by Alaska Airlines in some form to offset the horrendous service we received, we will be relaying our experience to family and friends and on social media, and doing all we can to urge everyone to avoid utilizing your services.

I got an email 3 hours before the flight letting me know it got canceled

The internet was down, which made my work plans impossible while inflight.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

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.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Packed in plane small uncomfortable seats elbow to elbow nobody wants to be in that situation for the money they paid

Overall flight was ok. Flight attendant was receptive to assisting passengers with tight connections.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight 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.