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Find cheap flights from Portland to Massachusetts from $96

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 6/26. 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
Mon 7/8
Mon 7/15

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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$149
West Tisbury
West Tisbury1 stop$1,093
Albany
Albany2 stops$351

Good to know

Low season

February

High season

July

Cheapest flight

$96
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 10% more expensive 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 10333 reviews
8.2Boarding
8.6Crew
7.4Food
8.0Entertainment
7.9Comfort
Airline reviews

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

2.0 MediocreJim, Jun 2024ATL - ANC
Read more about Delta reviews

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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

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.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

Flight was delayed due to the late arrival of the catering truck, which is quite unacceptable. There was a beverage service, but no pretzel, or cookie, or nuts were served in coach.

Not worth the price of premium class ticket paid, felt more like steerage.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

I had a great flight. Everything went smoothly and the flight arrived early.

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Terrible. I didn’t fly and I had an important meeting the next day.

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Wretched scheduling - they got themselves into a critical crew situation and didn’t try to address it until 15 minutes before they had to cancel my flight

Not much food/snacks. I had just tea and it was so bitter.

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

9/4Wed
1 stopSpirit Airlines
20h 57mPDX-BOS
9/11Wed
1 stopSpirit Airlines
20h 53mBOS-PDX
$149
9/9Mon
1 stopSpirit Airlines
20h 57mPDX-BOS
9/17Tue
2 stopsSpirit Airlines
17h 32mBOS-PDX
$168
8/31Sat
1 stopDelta
10h 18mPDX-BOS
9/5Thu
1 stopDelta
12h 26mBOS-PDX
$248
10/10Thu
nonstopJetBlue
5h 16mPDX-BOS
10/12Sat
nonstopJetBlue
6h 06mBOS-PDX
$287
8/27Tue
nonstopJetBlue
5h 14mPDX-BOS
9/1Sun
nonstopJetBlue
6h 10mBOS-PDX
$297
6/18Tue
1 stopUnited Airlines
8h 33mPDX-BOS
6/19Wed
1 stopUnited Airlines
10h 06mBOS-PDX
$345
11/28Thu
2 stopsDelta
7h 31mPDX-ALB
12/8Sun
1 stopDelta
7h 18mALB-PDX
$351
11/28Thu
1 stopUnited Airlines
6h 55mPDX-ALB
12/8Sun
1 stopUnited Airlines
8h 37mALB-PDX
$380
9/10Tue
2 stopsAmerican Airlines
11h 26mPDX-BDL
9/15Sun
1 stopAmerican Airlines
9h 17mBDL-PDX
$381
7/16Tue
1 stopAmerican Airlines
10h 10mPDX-BDL
7/23Tue
1 stopAmerican Airlines
8h 37mBDL-PDX
$386

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Recent one-way flight deals

6/26Wed
1 stopSpirit Airlines
21h 45mPDX-BOS
$96
7/16Tue
2 stopsSpirit Airlines
12h 16mPDX-BDL
$101
8/21Wed
nonstopJetBlue
5h 14mPDX-BOS
$129
8/31Sat
nonstopJetBlue
5h 15mPDX-BOS
$139
7/12Fri
1 stopDelta
7h 59mPDX-ALB
$183
8/5Mon
1 stopDelta
6h 55mPDX-BDL
$188
7/16Tue
1 stopAmerican Airlines
9h 21mPDX-BDL
$198
6/18Tue
1 stopUnited Airlines
8h 33mPDX-BOS
$208
6/18Tue
1 stopUnited Airlines
8h 33mPDX-BOS
$209
7/16Tue
2 stopsAmerican Airlines
12h 29mPDX-ALB
$239

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Last minute flights from Portland to Massachusetts

Last minute flight, train and bus deals

6/12Wed
multi-stopSpirit Airlines
21h 45mPDX-BOS
6/19Wed
multi-stopSpirit Airlines
19h 23mBOS-PDX
$223
6/13Thu
multi-stopSpirit Airlines
21h 45mPDX-BOS
6/17Mon
multi-stopSpirit Airlines
19h 23mBOS-PDX
$242
6/12Wed
multi-stopDelta
7h 28mPDX-BOS
6/16Sun
multi-stopDelta
7h 58mBOS-PDX
$406
6/13Thu
multi-stopAmerican Airlines
11h 34mPDX-BOS
6/17Mon
multi-stopAmerican Airlines
9h 14mBOS-PDX
$427
6/11Tue
multi-stopAmerican Airlines
10h 03mPDX-BOS
6/19Wed
multi-stopAmerican Airlines
9h 14mBOS-PDX
$451
6/10Mon
multi-stopUnited Airlines
9h 14mPDX-BOS
6/13Thu
multi-stopUnited Airlines
10h 06mBOS-PDX
$492
6/11Tue
multi-stopUnited Airlines
12h 04mPDX-BOS
6/13Thu
multi-stopUnited Airlines
10h 06mBOS-PDX
$497
6/9Sun
nonstopJetBlue
5h 24mPDX-BOS
6/12Wed
nonstopJetBlue
6h 10mBOS-PDX
$727
6/10Mon
nonstopJetBlue
5h 24mPDX-BOS
6/14Fri
nonstopJetBlue
6h 18mBOS-PDX
$767
6/9Sun
multi-stopDelta
9h 59mPDX-BOS
6/13Thu
multi-stopDelta
9h 33mBOS-PDX
$856

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Portland - Massachusetts Flights

Departure:

Portland (PDX)United States

Return flight deals:

Massachusetts - Portland

Cabin classes:

$878
$1,853
$1,926
$148