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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 5/29. 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 6/15
Sat 6/22

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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$133
West Tisbury
West Tisbury2 stops$352
Albany
Albany1 stop$386

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

  • Morning departure is around 5% 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 10673 reviews
8.6Crew
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

4.0 OkayReginald, May 2024MCI - LGA
Read more about Delta reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

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

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

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.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

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

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

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

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..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

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.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

Great TV, easy boarding, wonderful ground crew and flight crew.

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

5/28Tue
1 stopSpirit Airlines
17h 33mPDX-BOS
6/1Sat
1 stopSpirit Airlines
9h 15mBOS-PDX
$133
5/29Wed
1 stopSpirit Airlines
7h 50mPDX-BOS
6/5Wed
1 stopSpirit Airlines
21h 39mBOS-PDX
$139
8/27Tue
1 stopDelta
8h 14mPDX-BOS
9/1Sun
1 stopDelta
8h 14mBOS-PDX
$248
8/23Fri
1 stopDelta
7h 02mPDX-BOS
9/5Thu
1 stopDelta
10h 15mBOS-PDX
$273
8/15Thu
1 stopUnited Airlines
9h 19mPDX-BOS
9/1Sun
1 stopUnited Airlines
8h 41mBOS-PDX
$298
8/27Tue
nonstopJetBlue
5h 19mPDX-BOS
9/2Mon
nonstopJetBlue
6h 10mBOS-PDX
$307
6/14Fri
1 stopAmerican Airlines
9h 56mPDX-ALB
6/21Fri
1 stopAmerican Airlines
9h 47mALB-PDX
$386
8/14Wed
1 stopAmerican Airlines
9h 42mPDX-ALB
8/24Sat
1 stopAmerican Airlines
13h 52mALB-PDX
$390
8/13Tue
1 stopUnited Airlines
6h 55mPDX-ALB
8/24Sat
1 stopUnited Airlines
8h 16mALB-PDX
$417
8/21Wed
1 stopJetBlue
10h 12mPDX-HYA
8/27Tue
1 stopJetBlue
11h 20mHYA-PDX
$810

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Recent one-way flight deals

5/29Wed
1 stopSpirit Airlines
7h 50mPDX-BOS
$62
9/7Sat
1 stopSpirit Airlines
7h 28mPDX-BOS
$70
9/3Tue
1 stopDelta
7h 02mPDX-BOS
$148
7/25Thu
nonstopJetBlue
5h 19mPDX-BOS
$149
5/30Thu
nonstopJetBlue
5h 23mPDX-BOS
$169
5/28Tue
1 stopDelta
7h 10mPDX-BOS
$174
9/7Sat
1 stopAmerican Airlines
7h 16mPDX-BDL
$203
7/2Tue
1 stopUnited Airlines
7h 30mPDX-ALB
$204
5/26Sun
1 stopAmerican Airlines
9h 50mPDX-BOS
$207
6/30Sun
1 stopUnited Airlines
7h 42mPDX-BOS
$209

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Last minute flights from Portland to Massachusetts

Last minute flight, train and bus deals

5/21Tue
multi-stopSpirit Airlines
7h 38mPDX-BOS
6/4Tue
multi-stopSpirit Airlines
9h 17mBOS-PDX
$176
5/21Tue
multi-stopSpirit Airlines
7h 38mPDX-BOS
6/3Mon
multi-stopSpirit Airlines
9h 15mBOS-PDX
$187
5/20Mon
multi-stopDelta
7h 10mPDX-BOS
6/3Mon
multi-stopDelta
8h 12mBOS-PDX
$422
5/17Fri
multi-stopDelta
8h 06mPDX-BOS
5/27Mon
multi-stopDelta
11h 05mBOS-PDX
$456
5/17Fri
multi-stopAmerican Airlines
8h 53mPDX-BOS
5/27Mon
multi-stopAmerican Airlines
10h 25mBOS-PDX
$502
5/17Fri
multi-stopAmerican Airlines
8h 53mPDX-BOS
5/27Mon
multi-stopAmerican Airlines
10h 25mBOS-PDX
$533
5/21Tue
nonstopJetBlue
5h 27mPDX-BOS
6/3Mon
nonstopJetBlue
6h 10mBOS-PDX
$547
5/17Fri
multi-stopUnited Airlines
7h 39mPDX-BOS
5/19Sun
multi-stopUnited Airlines
9h 04mBOS-PDX
$596
5/21Tue
multi-stopUnited Airlines
11h 58mPDX-BOS
6/4Tue
multi-stopUnited Airlines
12h 50mBOS-PDX
$597
5/19Sun
nonstopJetBlue
5h 27mPDX-BOS
5/21Tue
nonstopJetBlue
6h 15mBOS-PDX
$647

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Portland - Massachusetts Flights

Departure:

Portland (PDX)United States

Return flight deals:

Massachusetts - Portland

Cabin classes:

$878
$1,851
$1,638
$148