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Find cheap flights from Portland to Massachusetts from $62

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 6/11. 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
Thu 6/27
Thu 7/4

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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
Nantucket
Nantucket2 stops$505
West Tisbury
West Tisbury1 stop$913
Albany
Albany1 stop$346

Good to know

Low season

February

High season

July

Cheapest flight

$62
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

  • Looking for a cheap flight? 25% of our users found tickets from Portland to the following destinations at these prices or less: Boston $168 one-way - $258 round-trip
  • Morning departure is around 17% 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 10502 reviews
8.2Boarding
7.4Food
7.9Comfort
8.6Crew
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

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

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

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

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

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.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

The Wi-Fi was unavailable on this flight for some reason.

On time take off…US cabins look tired and need of refresh!

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.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Flight was 1/2 hour delayed leaving Phoenix. Otherwise it was an average flight. Flight crew on this trip was very nice.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

Was lucky to have a employee at the AA checkin counter that had compassion and understood they ordeal that we went through with our original flight being diverted, needing to stay in the aircraft and then flying to the original destination; adding hours to the trip and forcing us to miss our connection and our rebooked connection. She was able to get up on standby on the highest priority on the next flight to the closest airport we need to be at and it all worked out despite being many hours late.

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..

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.

There was no food or entertainment on this flight. Great flight crew though

Book cheap flights from Portland to Massachusetts

Recent round-trip flight deals

9/4Wed
1 stopSpirit Airlines
7h 28mPDX-BOS
9/11Wed
1 stopSpirit Airlines
9h 22mBOS-PDX
$132
9/9Mon
1 stopSpirit Airlines
17h 35mPDX-BOS
9/21Sat
1 stopSpirit Airlines
9h 22mBOS-PDX
$133
9/6Fri
1 stopDelta
10h 12mPDX-BOS
9/17Tue
1 stopDelta
8h 21mBOS-PDX
$248
9/1Sun
1 stopDelta
10h 12mPDX-BOS
9/18Wed
1 stopDelta
8h 21mBOS-PDX
$273
9/4Wed
nonstopJetBlue
5h 16mPDX-BOS
9/18Wed
nonstopJetBlue
6h 06mBOS-PDX
$277
9/1Sun
nonstopJetBlue
5h 14mPDX-BOS
9/18Wed
nonstopJetBlue
6h 06mBOS-PDX
$287
8/16Fri
1 stopAmerican Airlines
9h 56mPDX-ALB
8/23Fri
1 stopAmerican Airlines
9h 04mALB-PDX
$346
8/27Tue
1 stopAmerican Airlines
7h 49mPDX-ALB
9/3Tue
2 stopsAmerican Airlines
12h 34mALB-PDX
$350
8/14Wed
1 stopUnited Airlines
7h 42mPDX-BDL
8/19Mon
1 stopUnited Airlines
8h 52mBDL-PDX
$418
8/13Tue
1 stopUnited Airlines
7h 07mPDX-BDL
8/18Sun
1 stopUnited Airlines
8h 29mBDL-PDX
$425

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Recent one-way flight deals

6/11Tue
1 stopSpirit Airlines
16h 51mPDX-BOS
$62
6/4Tue
1 stopSpirit Airlines
7h 38mPDX-BOS
$72
7/15Mon
1 stopUnited Airlines
8h 30mPDX-BOS
$124
8/26Mon
2 stopsAmerican Airlines
10h 32mPDX-BOS
$129
9/4Wed
nonstopJetBlue
5h 16mPDX-BOS
$139
8/31Sat
1 stopDelta
9h 30mPDX-BOS
$149
9/19Thu
nonstopJetBlue
5h 16mPDX-BOS
$159
8/1Thu
2 stopsAmerican Airlines
11h 45mPDX-ACK
$169
7/31Wed
1 stopUnited Airlines
6h 55mPDX-ALB
$173
6/11Tue
1 stopDelta
7h 28mPDX-BOS
$174

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Last minute flights from Portland to Massachusetts

Last minute flight, train and bus deals

6/1Sat
multi-stopSpirit Airlines
17h 45mPDX-BOS
6/8Sat
multi-stopSpirit Airlines
11h 39mBOS-PDX
$283
6/2Sun
multi-stopSpirit Airlines
17h 45mPDX-BOS
6/3Mon
multi-stopSpirit Airlines
27h 10mBOS-PDX
$303
6/2Sun
multi-stopDelta
7h 10mPDX-BOS
6/10Mon
multi-stopDelta
11h 56mBOS-PDX
$382
5/29Wed
multi-stopAmerican Airlines
9h 50mPDX-BOS
6/5Wed
multi-stopAmerican Airlines
9h 35mBOS-PDX
$418
5/29Wed
multi-stopAmerican Airlines
8h 53mPDX-BOS
6/3Mon
multi-stopAmerican Airlines
9h 22mBOS-PDX
$424
6/1Sat
multi-stopDelta
7h 10mPDX-BOS
6/3Mon
multi-stopDelta
11h 05mBOS-PDX
$456
5/31Fri
multi-stopUnited Airlines
8h 02mPDX-BOS
6/8Sat
multi-stopUnited Airlines
10h 06mBOS-PDX
$552
5/29Wed
multi-stopUnited Airlines
8h 02mPDX-BOS
6/3Mon
multi-stopUnited Airlines
14h 00mBOS-PDX
$561
5/30Thu
nonstopJetBlue
5h 23mPDX-BOS
6/2Sun
nonstopJetBlue
6h 10mBOS-PDX
$647
6/1Sat
nonstopJetBlue
5h 24mPDX-BOS
7/1Mon
nonstopJetBlue
6h 18mBOS-PDX
$687

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Portland - Massachusetts Flights

Departure:

Portland (PDX)United States

Return flight deals:

Massachusetts - Portland

Cabin classes:

$878
$1,913
$1,926
$148