$104 Find Cheap Flights from Oregon to Massachusetts

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Low seasonJanuary
High seasonJuly
Cheapest flight$104
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 1% 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.

  • 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 $192.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Wednesday where round-trip tickets can be as cheap as $392. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $479 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 evening, when round-trip flights cost $253 on average. Morning departures are around 113% more expensive than evening flights, 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 $539.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Oregon found in the last 72 hours was to Boston, at $118 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 $118.

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

    The cheapest month for flights from Oregon to Massachusetts is February, when tickets cost $309 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $539 and $474 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Oregon to Massachusetts takes 9h 35m, covering a distance of 2442 miles. The shortest route is Portland (PDX) to Boston (BOS) with an average flight time of 5h 19m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (87% of total searches to Massachusetts). The next most popular destinations are Hartford (11%) and West Tisbury (1%). Searches for flights to Nantucket (1%), to Provincetown (0%) and to Hyannis (0%) are also popular.

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.
8.0
Alaska AirlinesOverall score based on 9968 reviews
7.9Comfort
7.1Food
8.5Crew
7.1Entertainment
8.2Boarding
Airline reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

8.0 ExcellentAnonymous, Apr 2025PDX - PHX
Read more Alaska Airlines reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

Boarding was quick and easy as always the crew is on their game as always I always have an enjoyable flight so I’m good.

It was alright other than the changes in the Alaska Lounge. That and the migraine I had were disappointing. Other then that everything went well.

It was a short flight so no refreshments or entertainment which was fine.

No food, just a snack on a Seattle to Boston flight? VERY chintzy.

Flying in both directions across country the gate designated on my boarding pass was wrong. From w to e across the country the passenger next to me coughed the entire way.

Although both planes (flights) had mechanical issue delaying both of my flights, the crew members handled everything with ease. Both flights had the smoothest take off and landing. I opted to upgrade my seat to first class and really lucked out getting the seat at the very front of the plane. Awesome treat to myself. I really enjoyed my flight.

The staff from check-in counter to the flight crew were great. Flight was right on schedule. 10/10

Changed flight from San Fran to Seattle Then with a Delayed takeoff barely made my connection Waited over an hour for luggage 😜

It was good. There was a mistake made in Seattle. Somehow we were bumped out of our seats as if we weren't on the flight anymore. The woman at the gate caught it and announced our name to come up and she fixed it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

A bit rush for transit. Food and entertainment are not available

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

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.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

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

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Love the mosaic program, being able to move to an extra space seat for free is awesome

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Book cheap flights from Oregon to Massachusetts

Recent round-trip flight deals

5/17Sat
1 stopAlaska Airlines
7h 12mPDX-BOS
5/21Wed
1 stopAlaska Airlines
12h 58mBOS-PDX
$216
5/29Thu
nonstopHawaiian Airlines
5h 28mPDX-BOS
5/31Sat
nonstopHawaiian Airlines
6h 12mBOS-PDX
$217
5/28Wed
1 stopUnited Airlines
7h 40mPDX-BOS
6/4Wed
1 stopUnited Airlines
9h 46mBOS-PDX
$222
5/21Wed
1 stopDelta
7h 38mPDX-BOS
5/25Sun
1 stopDelta
12h 13mBOS-PDX
$237
6/11Wed
1 stopDelta
10h 22mPDX-BOS
6/15Sun
1 stopDelta
8h 34mBOS-PDX
$258
6/28Sat
nonstopJetBlue
5h 20mPDX-BOS
7/9Wed
nonstopJetBlue
6h 20mBOS-PDX
$262
6/28Sat
nonstopJetBlue
5h 20mPDX-BOS
7/3Thu
nonstopJetBlue
6h 20mBOS-PDX
$292
5/16Fri
1 stopUnited Airlines
7h 20mPDX-BOS
5/20Tue
1 stopUnited Airlines
9h 53mBOS-PDX
$303
6/9Mon
1 stopAmerican Airlines
7h 57mPDX-ALB
6/17Tue
1 stopAmerican Airlines
7h 48mALB-PDX
$307
6/9Mon
2 stopsAmerican Airlines
9h 19mPDX-ALB
6/17Tue
1 stopAmerican Airlines
7h 48mALB-PDX
$312

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Recent one-way flight deals

10/21Tue
1 stopUnited Airlines
7h 46mPDX-BOS
$104
6/10Tue
1 stopAlaska Airlines
11h 10mPDX-BOS
$108
6/17Tue
1 stopDelta
7h 11mPDX-BOS
$119
6/3Tue
2 stopsSpirit Airlines
19h 44mPDX-BOS
$121
5/29Thu
2 stopsSpirit Airlines
23h 47mPDX-BOS
$129
7/12Sat
1 stopJetBlue
9h 06mPDX-MVY
$144
6/17Tue
nonstopJetBlue
5h 20mPDX-BOS
$149
6/3Tue
1 stopDelta
6h 50mPDX-ALB
$154
6/11Wed
1 stopAmerican Airlines
9h 02mPDX-BDL
$154
7/29Tue
2 stopsAmerican Airlines
9h 56mPDX-BDL
$159

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Last minute flights from Oregon to Massachusetts

Last minute flight, train and bus deals

5/5Mon
multi-stopUnited Airlines
10h 16mMFR-BOS
5/9Fri
multi-stopUnited Airlines
8h 56mBOS-MFR
$452
5/5Mon
multi-stopUnited Airlines
12h 34mMFR-BOS
5/9Fri
multi-stopUnited Airlines
10h 06mBOS-MFR
$457
5/5Mon
multi-stopDelta
9h 50mPDX-BOS
5/9Fri
multi-stopDelta
8h 03mBOS-PDX
$597
5/4Sun
multi-stopAmerican Airlines
8h 54mPDX-BOS
5/8Thu
multi-stopAmerican Airlines
12h 19mBOS-PDX
$602
5/3Sat
multi-stopAlaska Airlines
7h 44mPDX-BOS
5/5Mon
multi-stopAlaska Airlines
16h 37mBOS-PDX
$626
5/3Sat
multi-stopAmerican Airlines
8h 38mPDX-BDL
5/10Sat
multi-stopAmerican Airlines
13h 02mBDL-PDX
$637
5/2Fri
nonstopJetBlue
5h 19mPDX-BOS
5/10Sat
nonstopJetBlue
6h 02mBOS-PDX
$649
5/5Mon
multi-stopAlaska Airlines
7h 28mRDM-BOS
5/12Mon
multi-stopAlaska Airlines
25h 22mBOS-RDM
$654
5/3Sat
multi-stopDelta
7h 00mPDX-BOS
5/8Thu
multi-stopDelta
11h 19mBOS-PDX
$687
5/1Thu
nonstopJetBlue
5h 19mPDX-BOS
5/6Tue
nonstopJetBlue
6h 02mBOS-PDX
$688

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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.

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