$99 Find Cheap Flights from Massachusetts to Oregon

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Low seasonJanuary
High seasonJuly
Cheapest flight$99
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 4% 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 $221.

  • What is the cheapest day to fly to Oregon?

    Based on KAYAK data, the cheapest day to fly to Oregon is Thursday 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 $494 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 $371 on average. Morning departures are around 4% 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 $423.

  • What is the cheapest flight to Oregon?

    The cheapest ticket to Oregon from Massachusetts found in the last 72 hours was to Portland, at $172 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 $172.

  • 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 8h 49m, covering a distance of 2461 miles. The shortest route is Boston (BOS) to Portland (PDX) with an average flight time of 6h 05m.

  • What are the most popular destinations in Oregon?

    Based on KAYAK flight searches, the most popular destination is Boise (45% of total searches to Oregon). The next most popular destinations are Eugene (24%) and Redmond (17%). Searches for flights to Medford (11%) and to North Bend (3%) are also popular.

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
8.1Boarding
7.8Comfort
7.1Entertainment
7.1Food
8.5Crew
Airline reviews

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.

6.0 GoodAnonymous, Jun 2025OGG - PDX
Read more Alaska Airlines reviews

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!

I can honestly say in the 54 years of my life this was the worst flying experience I have ever had. I was delayed on the tarmac going into Dallas for an hour and 2 hours on the tarmac leaving Dallas. a 4 hour flight turned into a 6 hour flight due to Alaska incompetence. To be honest I will never take another Alaska flight.

I am mobility challenged and ground crew were accommodating to my needs. One must walk up a ramp to board Alaska planes. Terminal to tarmac to ramp to plane.

The attendances were very thorough and pleasant during the entire trip. The pilots did an excellent job keeping us posted on what to expect. The landing in Portland was executed professionally and perfectly. Boarding was delayed a half hour. But given the times were in, that was no surprise. All in all, my preference is to fly only Alaska Airlines for their reliability and professional service.

Awesome just like that we have a timeline flying Alaska.

All good! No entertainment on this new plane yet but ok for this short flight. Great on time flight! Thanks

These questions are hard to answer. It was not until I checked in that I learned my flight was going to Seattle for a connection and not Portland. I did not get notified, or asked, about this change by Alaska or Kayak. Thankfully I made this flight; but missed the connecting flight and it took me much longer to get home. A service representative for Alaska says this happens frequently with third party companies, like Kayak. Please please figure that out.

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

Flight was canceled with no voucher of any kind and next available flight was two days later.

Boarding was chaotic. Microphone not working properly and second agent was distracted from task with baggage and late arrivals.

I DID NOT GO TO HAWAII ON HAWAIIAN AIRLINES. YOU DID NOT INFORM ME THAT BY CHOOSING BASIC ECONOMY, I MIGHT BE REQUIRED TO FLY STANDBY. I AM ELDERLY AS WAS MY COMPANION WHO IS ALSO SEVERELY DISABLED AND THERE WOULD BE NO WAY WE COULD TRAVEL ON STANDBY. THEY TOLD ME THAT ALL OF THE BASIC ECONOMY SEATS HAD BEEN SELECTED BY OTHER PASSENGERS AND WE HAD TO PAY AN ADDITIONAL $942 TO GET A SECURED SEAT ON THE PLAN AND, IN SPITE OF THE ADDITIONAL COST, WE WERE NOT ALLOW US TO AMEND OUR TRAVEL PLANS TO EXTEND OUR VACATION. ULTIMATELY, THE FLIGHT WAS DELAYED. WE WERE OFFERED A REFUND IF WE CANCELED OUR TRIP ALTOGETHER WHICH WE DID. IT IS YOUR DUTY TO INFORM YOUR CUSTOMERS OF THE POTENTIAL PROBLEMS THEY MAY FACE, AND YOU DID NOT DO SO. I WILL NOT UTILIZE YOUR SERVICES EVER AGAIN.

It was very pleasant. The staff and crew are very polite.

On time. Alaska upgraded seat comfort with memory foam seat covers with head rests

the people at the counter, NEED TO BE MORE HELPFUL. we had three suitcases to check in and we were not trying to be an INCONVENIENCE TO YOUR clerks. but she was not helpful and made our trip back home memorable but not IN A GOOD WAY. Sadly to say, you guys need to teach to be and to go above and beyond to help THE CUSTOMER BY ANY MEANS POSSIBLE. they need to leave aside whatever they are going thru in their lives, THEIR WORK DEMANDS THAT OF THEM, IF NOT THEY ARE NOT IN THE JOB THEY SUPPOSED TO.

Because the airport is under construction and because Hawaiian air just changed terminals we missed boarding out flight by 5 minutes. That cost me a night in an airport hotel and several hours of rebooking to make it to my destination. Costumers need to know that airport construction is a problem and they need to add an hour to deal with the air train delays from Federal Circle.

Half of my family members didn’t make it because they involuntary bumped off . And their seats where given away

Hawaiian Airlines staff is always professional & quick & easy check in & boarding process

Customer service by Susan of Alaskan Air was outstanding. We missed our flight out of JFK. She got us rebooked the following day. Way to go Susan.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

Smooth flight, especially take off and landing, and great crew on board. Really loved the stroopwaffles!

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.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

Book cheap flights from Massachusetts to Oregon

Recent round-trip flight deals

7/15Tue
nonstopJetBlue
6h 20mBOS-PDX
7/22Tue
nonstopJetBlue
5h 20mPDX-BOS
$197
7/9Wed
nonstopJetBlue
6h 20mBOS-PDX
7/13Sun
nonstopJetBlue
5h 20mPDX-BOS
$207
8/20Wed
1 stopDelta
7h 53mBOS-PDX
8/27Wed
1 stopDelta
10h 20mPDX-BOS
$217
9/4Thu
1 stopAlaska Airlines
8h 19mBOS-EUG
9/9Tue
1 stopAlaska Airlines
7h 48mEUG-BOS
$218
9/21Sun
1 stopDelta
8h 21mBOS-PDX
9/24Wed
1 stopDelta
9h 16mPDX-BOS
$227
8/12Tue
1 stopUnited Airlines
9h 11mBOS-PDX
8/15Fri
1 stopUnited Airlines
7h 47mPDX-BOS
$237
8/30Sat
1 stopAlaska Airlines
11h 04mBOS-EUG
9/4Thu
1 stopAlaska Airlines
14h 10mEUG-BOS
$238
8/30Sat
1 stopUnited Airlines
9h 01mBOS-EUG
9/4Thu
2 stopsUnited Airlines
10h 55mEUG-BOS
$264
8/29Fri
nonstopHawaiian Airlines
6h 09mBOS-PDX
9/5Fri
1 stopHawaiian Airlines
7h 59mPDX-BOS
$272
9/6Sat
1 stopHawaiian Airlines
8h 50mBOS-BOI
9/13Sat
1 stopHawaiian Airlines
9h 14mBOI-BOS
$284

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Recent one-way flight deals

7/9Wed
nonstopJetBlue
6h 20mBOS-PDX
$99
8/26Tue
1 stopHawaiian Airlines
8h 04mBOS-PDX
$108
9/9Tue
1 stopDelta
8h 06mBOS-PDX
$109
11/13Thu
1 stopDelta
8h 16mBOS-PDX
$119
7/15Tue
1 stopAlaska Airlines
16h 26mBOS-PDX
$124
9/18Thu
1 stopAlaska Airlines
8h 19mBOS-RDM
$129
8/21Thu
1 stopAmerican Airlines
9h 04mBOS-RDM
$130
9/23Tue
2 stopsAmerican Airlines
11h 15mBOS-RDM
$135
8/23Sat
2 stopsUnited Airlines
12h 05mALB-PDX
$163
8/21Thu
2 stopsUnited Airlines
10h 46mBOS-RDM
$166

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Last minute flights from Massachusetts to Oregon

Last minute flight, train and bus deals

6/16Mon
multi-stopDelta
10h 39mBOS-PDX
6/24Tue
multi-stopDelta
9h 50mPDX-BOS
$412
6/17Tue
multi-stopSpirit Airlines
21h 33mBOS-PDX
6/24Tue
multi-stopSpirit Airlines
24h 25mPDX-BOS
$444
6/17Tue
nonstopJetBlue
6h 20mBOS-PDX
7/2Wed
nonstopJetBlue
5h 20mPDX-BOS
$502
6/17Tue
multi-stopUnited Airlines
9h 46mBOS-PDX
7/2Wed
multi-stopUnited Airlines
10h 11mPDX-BOS
$512
6/17Tue
nonstopJetBlue
6h 20mBOS-PDX
6/23Mon
nonstopJetBlue
5h 20mPDX-BOS
$532
6/17Tue
multi-stopAlaska Airlines
10h 34mBOS-EUG
8/21Thu
multi-stopAlaska Airlines
14h 10mEUG-BOS
$555
6/17Tue
multi-stopAlaska Airlines
10h 34mBOS-EUG
8/21Thu
multi-stopAlaska Airlines
14h 10mEUG-BOS
$556
6/14Sat
multi-stopHawaiian Airlines
9h 20mBOS-PDX
6/17Tue
nonstopHawaiian Airlines
5h 25mPDX-BOS
$673
6/17Tue
multi-stopUnited Airlines
13h 50mBOS-BOI
6/24Tue
multi-stopUnited Airlines
11h 21mBOI-BOS
$687
6/13Fri
multi-stopHawaiian Airlines
8h 27mBOS-PDX
6/20Fri
nonstopHawaiian Airlines
5h 23mPDX-BOS
$697

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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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