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Find cheap flights from Portland to Massachusetts from $91

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 7/17. 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 7/6
Sat 7/13

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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 Tisbury2 stops$868
Albany
Albany1 stop$346

Good to know

Low season

February

High season

July

Cheapest flight

$91
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 6% 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 10368 reviews
8.0Entertainment
8.6Crew
7.4Food
7.9Comfort
8.2Boarding
Airline reviews

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

4.0 OkayDavwinder Singh, Jun 2024SEA - ATL
Read more about Delta reviews

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.

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!

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.

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.

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.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

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!

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

They cancelled two flight and got us onto another airline, which was also delayed.

Nothing, terrible travel experience due to weather and maintenance delays and was left stranded in Austin.

My husbands flight last night Vancouver/Sydney was 90 minutes late in leaving. My flight tonight Vancouver/Seattle was also late in departing.

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
21h 31mPDX-BOS
9/11Wed
1 stopSpirit Airlines
18h 56mBOS-PDX
$149
9/10Tue
1 stopSpirit Airlines
20h 57mPDX-BOS
9/17Tue
1 stopSpirit Airlines
20h 53mBOS-PDX
$160
9/21Sat
1 stopDelta
10h 35mPDX-BOS
10/1Tue
1 stopDelta
7h 54mBOS-PDX
$248
10/25Fri
1 stopDelta
10h 00mPDX-BOS
10/29Tue
1 stopDelta
9h 40mBOS-PDX
$262
10/10Thu
nonstopJetBlue
5h 16mPDX-BOS
10/15Tue
nonstopJetBlue
6h 06mBOS-PDX
$287
9/20Fri
nonstopJetBlue
5h 16mPDX-BOS
9/23Mon
nonstopJetBlue
6h 06mBOS-PDX
$297
8/21Wed
1 stopUnited Airlines
6h 53mPDX-ALB
8/26Mon
1 stopUnited Airlines
8h 16mALB-PDX
$346
8/19Mon
1 stopAmerican Airlines
9h 56mPDX-ALB
8/24Sat
2 stopsAmerican Airlines
13h 23mALB-PDX
$351
8/16Fri
2 stopsAmerican Airlines
11h 58mPDX-ALB
8/24Sat
2 stopsAmerican Airlines
13h 23mALB-PDX
$356
8/19Mon
1 stopUnited Airlines
31h 53mPDX-ALB
8/24Sat
1 stopUnited Airlines
8h 26mALB-PDX
$376

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Recent one-way flight deals

7/17Wed
1 stopSpirit Airlines
22h 00mPDX-BOS
$91
7/15Mon
1 stopSpirit Airlines
22h 00mPDX-BOS
$94
7/4Thu
1 stopJetBlue
9h 47mPDX-ACK
$110
8/3Sat
nonstopJetBlue
5h 17mPDX-BOS
$149
7/8Mon
1 stopDelta
7h 18mPDX-BOS
$174
9/13Fri
2 stopsAmerican Airlines
13h 29mPDX-ALB
$178
8/19Mon
2 stopsUnited Airlines
11h 17mPDX-BOS
$179
7/4Thu
2 stopsAmerican Airlines
11h 31mPDX-ACK
$179
9/17Tue
3 stopsUnited Airlines
13h 36mPDX-BOS
$184
9/13Fri
1 stopDelta
9h 06mPDX-ALB
$198

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Last minute flights from Portland to Massachusetts

Last minute flight, train and bus deals

6/11Tue
multi-stopSpirit Airlines
24h 18mPDX-BOS
7/10Wed
multi-stopSpirit Airlines
20h 06mBOS-PDX
$256
6/11Tue
multi-stopSpirit Airlines
24h 18mPDX-BOS
7/10Wed
multi-stopSpirit Airlines
20h 56mBOS-PDX
$267
6/11Tue
nonstopJetBlue
5h 24mPDX-BOS
7/10Wed
nonstopJetBlue
6h 18mBOS-PDX
$372
6/11Tue
multi-stopUnited Airlines
8h 02mPDX-BOS
6/17Mon
multi-stopUnited Airlines
10h 06mBOS-PDX
$412
6/10Mon
multi-stopUnited Airlines
8h 02mPDX-BOS
7/10Wed
multi-stopUnited Airlines
8h 44mBOS-PDX
$416
6/7Fri
multi-stopDelta
7h 28mPDX-BOS
6/10Mon
multi-stopDelta
10h 46mBOS-PDX
$496
6/10Mon
multi-stopAmerican Airlines
11h 34mPDX-BOS
6/14Fri
multi-stopAmerican Airlines
8h 20mBOS-PDX
$517
6/7Fri
nonstopJetBlue
5h 24mPDX-BOS
7/10Wed
nonstopJetBlue
6h 10mBOS-PDX
$547
6/8Sat
multi-stopAmerican Airlines
10h 03mPDX-BOS
6/14Fri
multi-stopAmerican Airlines
9h 35mBOS-PDX
$677
6/11Tue
multi-stopDelta
7h 13mPDX-BDL
6/17Mon
multi-stopDelta
7h 47mBDL-PDX
$726

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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