$109 Find Cheap Flights from Massachusetts to Oregon

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Low seasonJanuary
High seasonJuly
Cheapest flight$109
Best time to beat the crowds with an average 17% 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 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 $294.

  • 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 $365. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $483 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 $370 on average. Morning departures are around 3% more expensive than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the morning, which is peak travel time and where the average cost of a ticket is $415.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Massachusetts found in the last 72 hours was to Portland, at $159 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 $159.

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

    The cheapest month for flights from Massachusetts to Oregon is May, when tickets cost $464 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $657 and $636 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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

  • How long is the flight to Oregon?

    An average nonstop flight from Massachusetts to Oregon takes 9h 26m, covering a distance of 2461 miles. The shortest route is Boston (BOS) to Portland (PDX) with an average flight time of 6h 09m.

  • What are the most popular destinations in Oregon?

    Based on KAYAK flight searches, the most popular destination is Medford (41% of total searches to Oregon). The next most popular destinations are Boise (33%) and Eugene (13%). Searches for flights to Redmond (9%) and to North Bend (4%) 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 10000 reviews
7.8Comfort
7.1Food
8.5Crew
7.1Entertainment
8.1Boarding
Airline reviews

Wonderful staff who honored sleepy overnight travelers and still met needs quietly and quickly!

10.0 ExcellentAnonymous, Jun 2025HNL - PDX
Read more Alaska Airlines reviews

Wonderful staff who honored sleepy overnight travelers and still met needs quietly and quickly!

The setting on the loudspeaker was painful and the crew member who did the talking spoke very quickly and repetitively, with extra little jokes that were distracting and mostly unfunny. I doubt that the main messages penetrated the noise.

1. On time flights. All of our, three separate, flights for three families were late 2. No food on the 5 1/2 hour flight. A substantial snack would have been good. 3. Seat upgrades are expensive 4. No place to move around or stretch on the 5 1/2 hour flight

I like the new adjustable headrest. Unfortunately 2 crying children were in front of us. But it was the first time and not holding Alaska accountable for that. Alaska always seems to have everything in order professional but comfortable.

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

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

Thank you still providing bags for vomit. My son had a migraine and needed a bag to vomit in and it was right there behind the seat in front of us. Thank you!

Well, the baggage porter on Maui told my mom that our carry on luggage was overweight and if she gave him a 50 dollar tip he would let it go through. She tipped him and he tells us that he needs my Alaska airlines cc to waive the extra baggage charge. Find out later that since my original reservation was not under my name using a Hawaiian airlines CC, I would have to pay for the luggage anyway. I told them I had to end up paying for my daughters ticket when you all said because she turned two using my Alaska Airlines cc, now they need to charge me for her seat/flight, but you guys didn't care and i ended up paying for the bags and my mom paid the porter 50 dollars extra for nothing .. It was a crappy experience. First it was a multi trip. PDX-HNL then HNL-OGG then OGG to PDX. All bought under one ticket. My daugher turned two during the flight from HNL-OGG, but when I bought the ticket and at the PDX airport they said since i bought the ticket before she was two, everything is fine. come to find out no, I had to pay her ticket HNL-OGG and again OGG to PDX. you guys scammed me. You should say it on your website and make sure people know that during flights if the child turns two they have to pay for their seat. If i knew that from the very beginning i would have bought her ticket and it would have been LESS than paying TWICE for her flight! and you scammed my mother with you porter who told her to pay him 50 dollars and he would take care of the extra luggage weight.

Flight was great. Boarding was crazy because another flight was boarding late next to ours so everyone was standing and in the way.

It was a quick flight, but coffee would have been great!

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

I was unable to get a check im and get a boarding pass. I tried at the desk of the flight operator Alaska, was told to go to Hawaiian and almost had to go back to Alaskan. In the end inwas told to go thru security and directly to the gate without checking in. It would have been more helpful to have the details rather than walking all over the terminals trying to check in.

Nothing. Fare didn’t allow seat allocations. So we were stuck in the middle . Not good for 77 to 80 year olds. I was stick on plane. Taken off the plane before take off and ground staff told me to google where a hospital was to get a clearance to travel again. Left on own at airport ti fend for our selves. Also was charged for baggage, also I was not aware. I think booking through a third party, such as yourselves, doesn’t allow any for considerations when allocating seats.

I booked on Hawaiian and was bumped to an American airline flight in a different terminal. I was traveling with my two kids and told to take an air train to check my baggage in. We were given the last three seats in front of the toilet. Never flying Hawaiian again. Totally unreliable.

Good except that I couldn’t change seat and made me wait untill I checked in

The middle name gave us so much issue at check in we had done middle names when booking but Hawaiian/Alaska don’t recognize the middle names and gave us problems at check in. We have never experienced that before.

Everything was great except for the delayed flight times (it was delayed twice).

I was booked thru Hawaiian Airlines (HA) on Kayak in February. I got 2 confirmation emails from Hawaiian Airlines in February. Even though the flight ticket informed me the flight was marketed thru HA and operated by Alaska Airlines (AA), I was never given any confirmation codes or anything from Kayak or AA to check into my flight online ahead of time. They also couldn't find the HA flight number I was given on their website and was told my flight did not exist unless I searched thru the AA website for flight details that was similar to the info HA gave me. The only way to check into my flight and make sure the flight still existed required me to get there 4 hours early. When I arrived at the airport, HA desk told me to go to AA desk. First AA desk redirected me to another desk, second AA desk told me to find someone with an iPad, and finally the iPad rep was able to help me. I also had to chat with AA reps online the night previous to my return trip because the same issue occurred.

Traveling with my 90 year old mother, the boarding process was great, the gate crew was very helpful and friendly. One of the flight attendants was kind enough to assist her to and from the restroom mid-flight and cater to any requests she had. I wish I flew Hawaiian Airlines more often, it was a great trip!

I did not board neither one of my flights because It got delayed and I had to be at my destination at a certain time

We were delayed at the SD gate for close to an hour before we were allowed to depart for SJ. Reason given was inadequate ground crew to move the plane from the gate.

Boarded plane and then delayed 1.5 hours while on the plane

Survey sent before we actually left. Delay after delay. Now a crew problem.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

My flight was delayed a very short period of time but they did not hold my connecting flight to San Diego, also through United. So they closed the doors before we got off our plane. They would only have to help the door open for another five to ten minutes. So I missed a court deadline for a manditory mediation settlement conference for my client. I had to get an associate to be there in person and be on the phone with him relaying what he needs to do the entire time. The court was very upset with me and so was my client. United cannot be trusted.

Very rough getting into denver. my kid threw up it was so rough.

We were given vouchers we couldn’t use with a 5.5 hour delay

Cramped seat even in economy plus seat 10A. Over booked flight, no space for the bags

Why wasn't this flight departure scheduled eith another crew so that it could leave on time? When we arrived in Denver we had so little time between flights we had run to the connecting flight. We should received some credit for the inconvenience.

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.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Book cheap flights from Massachusetts to Oregon

Recent round-trip flight deals

8/22Fri
nonstopHawaiian Airlines
6h 09mBOS-PDX
8/31Sun
nonstopHawaiian Airlines
5h 30mPDX-BOS
$196
8/22Fri
nonstopHawaiian Airlines
6h 09mBOS-PDX
8/31Sun
nonstopHawaiian Airlines
5h 30mPDX-BOS
$199
8/25Mon
nonstopJetBlue
6h 11mBOS-PDX
8/27Wed
nonstopJetBlue
5h 22mPDX-BOS
$217
8/22Fri
nonstopJetBlue
6h 11mBOS-PDX
8/31Sun
nonstopJetBlue
5h 22mPDX-BOS
$219
7/30Wed
nonstopAlaska Airlines
6h 17mBOS-PDX
8/6Wed
1 stopAlaska Airlines
9h 15mPDX-BOS
$227
8/25Mon
1 stopAlaska Airlines
19h 30mBOS-PDX
8/31Sun
1 stopAlaska Airlines
20h 02mPDX-BOS
$236
7/23Wed
1 stopDelta
8h 30mBOS-PDX
7/29Tue
1 stopDelta
6h 40mPDX-BOS
$237
8/10Sun
1 stopUnited Airlines
8h 36mBOS-PDX
8/13Wed
1 stopUnited Airlines
8h 06mPDX-BOS
$271
9/6Sat
1 stopDelta
10h 13mBOS-BOI
9/13Sat
1 stopDelta
8h 59mBOI-BOS
$285
7/23Wed
1 stopUnited Airlines
9h 02mBOS-PDX
7/27Sun
1 stopUnited Airlines
8h 18mPDX-BOS
$298

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Recent one-way flight deals

8/26Tue
nonstopJetBlue
6h 11mBOS-PDX
$109
8/20Wed
2 stopsSouthwest
10h 30mBOS-PDX
$114
8/31Sun
1 stopAlaska Airlines
8h 04mBOS-PDX
$118
9/6Sat
nonstopHawaiian Airlines
6h 09mBOS-PDX
$139
8/26Tue
1 stopAlaska Airlines
10h 34mBOS-BOI
$142
10/18Sat
1 stopHawaiian Airlines
8h 25mBOS-EUG
$144
8/20Wed
1 stopDelta
7h 59mBOS-EUG
$145
7/16Wed
1 stopDelta
10h 28mBOS-PDX
$169
8/12Tue
2 stopsUnited Airlines
12h 25mBOS-BOI
$198
9/1Mon
1 stopUnited Airlines
7h 21mBOS-BOI
$201

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Last minute flights from Massachusetts to Oregon

Last minute flight, train and bus deals

7/8Tue
multi-stopSpirit Airlines
30h 33mBOS-PDX
7/28Mon
multi-stopSpirit Airlines
30h 07mPDX-BOS
$392
7/8Tue
nonstopJetBlue
6h 20mBOS-PDX
7/28Mon
nonstopJetBlue
5h 20mPDX-BOS
$402
7/8Tue
multi-stopAlaska Airlines
18h 50mBOS-PDX
7/28Mon
nonstopAlaska Airlines
5h 23mPDX-BOS
$412
7/8Tue
nonstopAlaska Airlines
6h 17mBOS-PDX
7/15Tue
multi-stopAlaska Airlines
9h 15mPDX-BOS
$462
7/8Tue
multi-stopUnited Airlines
9h 01mBOS-PDX
7/15Tue
multi-stopUnited Airlines
8h 18mPDX-BOS
$467
7/4Fri
multi-stopHawaiian Airlines
8h 35mBOS-PDX
7/28Mon
nonstopHawaiian Airlines
5h 23mPDX-BOS
$488
7/7Mon
multi-stopDelta
8h 30mBOS-PDX
7/14Mon
multi-stopDelta
6h 49mPDX-BOS
$497
7/4Fri
multi-stopUnited Airlines
9h 04mBOS-OTH
7/8Tue
multi-stopUnited Airlines
8h 10mOTH-BOS
$499
7/6Sun
multi-stopHawaiian Airlines
10h 35mBOS-PDX
7/28Mon
nonstopHawaiian Airlines
5h 23mPDX-BOS
$547
7/8Tue
multi-stopDelta
7h 02mBDL-BOI
7/15Tue
multi-stopDelta
9h 25mBOI-BDL
$622

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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.

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