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Find cheap flights from Portland to Massachusetts from $61

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Massachusetts departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/22
Sat 6/29

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Best Massachusetts Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston1 stop$132
West Tisbury
West Tisbury2 stops$297
Albany
Albany1 stop$346

Good to know

Low season

February

High season

July

Cheapest flight

$61
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Portland to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Portland 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 Portland to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts from Portland 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 Portland 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 to Massachusetts with an airline and back to Portland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland 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 to Massachusetts from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Massachusetts

  • Morning departure is around 4% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Portland to Massachusetts

 
Need help choosing which airline to fly with from Portland 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
DeltaOverall score based on 10561 reviews
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
8.6Crew
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

Fantastic. Smooth boarding with an infant. Never experienced it with any other carriers.

This was a Lufthansa flight, not United. The CSA at the counter, Ashley, was not only incompetent, but quite rude. Me and two other PAX waited over 7 minutes standing in front of her and another CSA and they ignored us. We joked that we must have accidently taken invisibility pills. She could have at least said "I'll be with you in a moment, I'm currently....". I could go on about how rude she and the other CSAs were (whispering, not communicating with me, blaming the situation on others, etc.). She would not work for me. Then, she gave me literally the worst seat on the plane. the worst. My seat kept getting bumped (rammed twice by the crew with their carts and about every 5 minutes by someone using the bathroom), listening to the bathroom all night, crowded seat, etc.

My seat was broken. WiFi didn’t work. Gate crew at HOU were rude and condescending. Treated all the passengers badly. Bad experience, United.

First flight of the day… MINIMUM FUEL! 15 minute landing delay at HOU due to fog turned into a 2+ hour delay! Rather than circle, they had to divert to another city to refuel! Sat on tarmac at Austin to refuel. We ALL missed our connections! The crew, including pilots, were clueless. Crew was really a mess. At HOU, Untied employees were exceedingly rude to all. It was pitiful.

An hour and a half late is UNACCEPTABLE. The negative impact to our family is unconscionable. And for the price we were forced to pay...

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

Delayed so that missed connecting flight. Connecting flight was also delayed on the tarmac but they closed the gate before the rescheduled time.

Attendants were rude. Scowling. Seats were miserable and we paid extra.

Took off over an hour late with multiple mechanical issues. Gate agent in Dallas was lazy and was slow as molasses. Had a line 10 people long. Spirit bad..

The flight was short. However, my bag was delayed and was put on another flight.

Flight attendant was incredible. Very efficient, friendly and pleasant. Patricia was one of the best I have ever seen. Please give her a big raise!

LIT to DFW - 3 hours late; the entire plane had been boarded before they told us there was a delay due to a weather-related ground stop in Dallas. DFW to MAY - 2+ hours late due to A/C needing to be repaired after everyone had boarded, then when we finally reach the runway, the First Officer timed out and we had to taxi all the way back to the gate and wait for a new one. I arrived in New Orleans 5+ hours later than I should have. Return flights were completely cancelled; rebooked through the app to fly through CLT instead of DFW. MSY to CLT had no issues, but CLT to LIT was delayed 1.25 hrs because flight attendants had not arrived to the airport yet. At least they didn’t make us all sit on the plane to wait for them. I should have driven.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in-flight WiFi. Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay that much for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a shitty attitude for no reason, nor will they act the way this woman did. Unacceptable.

Liked - nothing. Disliked - delayed 35+ min sitting on the plane. Caused me to miss my connection in Charlotte. American Airlines is the worst US Air Carrier company with atrocious customer service.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

The terminal this flight boarded from was so far away, poorly temperature controlled, and generally uncomfortable. The plane was small but the flight was short, so it wasn't so bad.

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

My experience was pretty frustrating because the first leg of my flight on United (though booked through Air Canada) was delayed causing me to miss my connecting flight on Air Canada. This could have been an easy solve as there was a direct flight later that morning via Air Canada that they easily could have put me on which would have only gotten me to my destination 2 1/2 hours later but because United and Air Canada don’t seem to have good communication they gave me the run around both telling me to talk with the other which I did three times to no avail. I ended up taking the delayed flight and getting on a new connecting flight which ended up getting me to my destination 6 hours later and I missed the event I was planning to go to this evening.

I was appalled to have to pay for just a regular seat when I went to book 24 hrs before my flight! Because it was only an hour flight I didn’t choose a seat from Grand Junction to Denver, but I did for Toronto and had to pay just to choose a regular available seat! In my 60+ years of flying this was the first time I have heard of this. Also, allowing people to bring on “huge “ suitcases, not carry on size, but much bigger, and then a large pack pack stuffed. So they take up all the room in the overhead bins and if we are later boarding, there is no room so we have to check our small carry on. I have already paid for and checked in one bag! I certainly will not choose to fly with United again unless it is the “only” airline available!

Fresh fuit or veg snacks would be so great, but there are two good restaurants in Denver airport. Try Etais UDIS or Freshens DIA for nutritious delicious pita sandwiches/ donairs and crepes in Freshens.

Crowded plane but it flew on time and had friendly staff

The Air Canada agent was very helpful helping with my luggage and cat carrier when I went there instead of United.

United force you to download their App to do the check-in.

It was fine. The seating was tight. My husband is 6' 2", so we were glad to get seats with no one in front of him. I was glad that the plane wasn't packed so I could spread out.

There is no food or entertainment on these short flights. Again the wheelchair situation in Denver is nasty. They are short staffed due to cut backs and layoffs and this impacts on travel comfort and ease.

Book cheap flights from Portland to Massachusetts

Recent round-trip flight deals

9/9Mon
1 stopSpirit Airlines
17h 35mPDX-BOS
9/18Wed
1 stopSpirit Airlines
9h 22mBOS-PDX
$132
9/9Mon
1 stopSpirit Airlines
17h 35mPDX-BOS
9/18Wed
1 stopSpirit Airlines
9h 22mBOS-PDX
$133
10/21Mon
1 stopDelta
10h 00mPDX-BOS
10/26Sat
1 stopDelta
9h 38mBOS-PDX
$248
9/18Wed
nonstopJetBlue
5h 16mPDX-BOS
9/25Wed
nonstopJetBlue
6h 06mBOS-PDX
$277
9/20Fri
1 stopDelta
7h 04mPDX-BOS
9/28Sat
1 stopDelta
11h 11mBOS-PDX
$293
8/16Fri
2 stopsAmerican Airlines
10h 42mPDX-MVY
8/24Sat
2 stopsAmerican Airlines
10h 57mMVY-PDX
$297
9/9Mon
nonstopJetBlue
5h 16mPDX-BOS
9/18Wed
nonstopJetBlue
6h 06mBOS-PDX
$297
8/12Mon
1 stopUnited Airlines
7h 30mPDX-ALB
8/20Tue
1 stopUnited Airlines
8h 16mALB-PDX
$346
8/12Mon
1 stopAmerican Airlines
9h 56mPDX-ALB
8/20Tue
2 stopsAmerican Airlines
11h 23mALB-PDX
$350
8/11Sun
1 stopUnited Airlines
7h 00mPDX-ALB
8/20Tue
1 stopUnited Airlines
10h 20mALB-PDX
$374

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Recent one-way flight deals

9/9Mon
1 stopSpirit Airlines
17h 35mPDX-BOS
$61
6/4Tue
1 stopSpirit Airlines
7h 38mPDX-BOS
$62
8/12Mon
1 stopUnited Airlines
8h 20mPDX-BOS
$124
7/25Thu
nonstopJetBlue
5h 14mPDX-BOS
$149
10/7Mon
nonstopJetBlue
5h 16mPDX-BOS
$159
9/1Sun
1 stopUnited Airlines
8h 01mPDX-BOS
$166
8/29Thu
1 stopAmerican Airlines
7h 44mPDX-BOS
$168
7/10Wed
1 stopAmerican Airlines
8h 14mPDX-BOS
$171
6/5Wed
1 stopDelta
7h 10mPDX-BOS
$174
9/23Mon
1 stopDelta
6h 58mPDX-BDL
$199

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Last minute flights from Portland to Massachusetts

Last minute flight, train and bus deals

5/28Tue
multi-stopSpirit Airlines
17h 33mPDX-BOS
6/10Mon
multi-stopSpirit Airlines
19h 23mBOS-PDX
$264
5/28Tue
multi-stopSpirit Airlines
17h 33mPDX-BOS
6/11Tue
multi-stopSpirit Airlines
19h 22mBOS-PDX
$268
5/28Tue
multi-stopSpirit Airlines
17h 33mPDX-BOS
6/12Wed
multi-stopSpirit Airlines
19h 23mBOS-PDX
$276
5/28Tue
multi-stopUnited Airlines
8h 02mPDX-BOS
6/12Wed
multi-stopUnited Airlines
10h 11mBOS-PDX
$374
5/28Tue
multi-stopDelta
7h 10mPDX-BOS
6/8Sat
multi-stopDelta
7h 50mBOS-PDX
$382
5/28Tue
multi-stopDelta
7h 10mPDX-BOS
6/11Tue
multi-stopDelta
7h 59mBOS-PDX
$416
5/27Mon
multi-stopUnited Airlines
8h 02mPDX-BOS
6/3Mon
multi-stopUnited Airlines
10h 06mBOS-PDX
$452
5/24Fri
multi-stopAmerican Airlines
8h 38mPDX-BOS
5/27Mon
multi-stopAmerican Airlines
10h 40mBOS-PDX
$495
5/25Sat
nonstopJetBlue
5h 23mPDX-BOS
5/31Fri
nonstopJetBlue
6h 12mBOS-PDX
$522
5/28Tue
multi-stopAmerican Airlines
10h 08mPDX-ALB
6/3Mon
multi-stopAmerican Airlines
8h 13mALB-PDX
$662

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Portland - Massachusetts Flights

Departure:

Portland (PDX)United States

Return flight deals:

Massachusetts - Portland

Cabin classes:

$878
$1,851
$1,922
$148