$128 Find Cheap Flights from Portland to Massachusetts - Compare and Save

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Cheap Flights from Portland to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Albany
6h 40m2 stops
from $267per person
Boston
5h 33mNonstop
from $294per person
Hartford
6h 32m2 stops
from $337per person
Provincetown
7h 06m3 stops
from $754per person
West Tisbury
9h 00m3 stops
from $1,319per person
New Bedford
15h 09m4 stops
from $1,348per person
Booking Insights

KAYAK's insights & trends for Portland to Massachusetts flights

Get data-powered insights and trends into flights from Portland to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Portland to Massachusetts?

Flight prices are below average for this route right now.

Flights to Massachusetts from Portland usually cost between $335 and $543 in December.
The lowest price found in the past 5 days was $294 on Southwest (Dec 3-Dec 16).

What is the cheapest Portland to Massachusetts flight route?

The cheapest ticket to Massachusetts from Portland found in the last 5 days was to Boston, at $297 round-trip. The most popular route is from Portland (PDX) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $297.

What is the cheapest time of day to fly to Massachusetts?

The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $368 on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $540.

Can I save money by flying with a layover from Portland to Massachusetts?

No, with an average price for the route of $433, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Portland to Massachusetts?

The cheapest month for flights from Portland to Massachusetts is January, when tickets cost $327 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is $529 and $484 respectively.

What’s the cheapest day of the week to fly from Portland to Massachusetts?

If your flying dates are flexible, you should consider flying to Massachusetts on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Portland to Massachusetts. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Portland to Massachusetts?

To get a below average price on the flight from Portland to Massachusetts, you should book around 4 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

February

Cheapest flight

$128
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Portland to Hartford

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 from Portland to Massachusetts 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 from Portland to Massachusetts with an airline and back 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 from Portland to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the 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.
7.9
Alaska AirlinesOverall score based on 12931 reviews
7.0Entertainment
8.5Crew
7.0Food
8.1Boarding
7.8Comfort
Airline reviews

Alaska has clean planes, modern interiors, and good service. Major drawback is the lack of IFE seat back screens. Otherwise it could really give Delta a run for its money.

8.0 ExcellentAnthony, Jul 2026
Read more Alaska Airlines reviews

Alaska has clean planes, modern interiors, and good service. Major drawback is the lack of IFE seat back screens. Otherwise it could really give Delta a run for its money.

Internet was great. It was nice to watch a movie. The crew was very nice.

Some food or at least snacks need to be offered on long flights. I thought I had ordered food for my husband and I prior to the flight, but was told during the flight that I had not. Perhaps, if you must charge extra for food, let people order on board. We did get some food, which evidently others had decided they didn’t want onboard, but it wasn’t very good. We did like the adherence to takeoff and landing times, and the quick return of our luggage.

Pretty smooth ride!… a little tight in the back and would’ve loved to had a movie screen… couldn’t beat the price to the West Coast!

Not having to pay 160$ for a 20 lb and 12 lb bag that were clearly under 50 lbs and they overcharged me for them

The direct service from Logan to PDX made travel so easy, I really appreciate this route. Pilots were very communicative with passengers about conditions and expectations. Everyone on staff was pleasant and helpful. Boarding was easy and efficient.

Seats are still too crowded and uncomfortable on long flights like this cross country one.

Food and entertainment were inferior to jet blue The pretzels were way too garlicky

Absolutely fine. No problems. I have mobility issues and they were perfectly addressed.

The obvious, the seats are too small. Great flight and nice staff. It was nice to be informed what was happening during the whole experience.

The crew were very respectful. And also they were welcoming.they did help us locate our seats.i enjoyed.

Terrible. Waited on runway for 1+ hour after landing and then was brought to wrong terminal

We got stuck on the tarmac taxiing after landing early so we didn’t get off the plane until an hour later than we thought we would

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

My seat had no padding, it was literally plywood with a plastic cover. I could not change seats on my 10 hour flight. My excitement for this trip helped me deal with the pain.

The flights were on time- Great service Would have liked more options for food choices.

The brakes on the A220 are sensitive and uncomfortably grabby

It was serviceable, nothing special but nothing awful on this leg.

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

We had a 90 minute delay due to equipment failure that was detected just before we took off. United rebooked my connecting flight.

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

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

Poor seating comfort, seat cushion too thin, very uncomfortable. My luggage didi not make the flight due to equipment change. At least. United had it delivered the next day. I was without my toilet items for one day.

Flight cancelled because of the grounded 737s. United was good about it and got us onto a later Alaska Airlines flight to Oakland (not San Francisco as originally intended). Had to go through security again and my wife dropped her MacBook Pro, which broke, a $2,500 whoopsie. But we made it home.

Luggage took too long go get off plane in Knoxville. Was almost 45 minutes after the flight landed.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

DFW-LHR Toilets not kept clean Too cramped. Aisles so narrow crew were constantly banging into people on the aisle seats. Even then, the carts used are reduced width. Other than that it was a decent flight on both legs

Excellent customer service at check in at Austin flight to DFW and excellent customer service from Karren in terminal B at DFW.

The flight itself was fine, but between the man in front of me putting his chair back, and the gentleman next to me who took up 50% of my seat, my back and neck are destroyed from the flight. I’m hoping for a better outcome flying back.

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

We were told there would be no food/beverage service due to turbulence. There was very little turbulence on the 2+ hour flight. I was in First Class and thought they could have done a quick service after take off as they had a quite bit of time before we would be reaching the predicted turbulent area. They could have at least passed out a quick bag of pretzels.

Very disappointed with the crew and the lack of attention given to the passengers. On a 5 hour flight they never offered a snack. One time offered a beverage and didn’t pick up the used cups until the flight was on final approach. The two flight attendants in our section mentioned that they were best friends and compared their pre flight shoes. When paying for first/business class there is a level of service that should be expected. These two spent the majority of the flight in their seats playing on their phones and laughing with each other. Very frustrating!!!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

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.

More options for your flight from Portland to Massachusetts

Complete your trip to Massachusetts with a hotel stay or car rental