$109 Find Cheap Flights from Portland to Massachusetts

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 4/1. 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
1 adult, Economy, 0 bags

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Massachusetts.
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Cheap Flights from Portland to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$197
Albany
Albany1 stop$374
Boston
Boston1 stop$197
Albany
Albany1 stop$374

Book Cheap Portland to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Massachusetts

Thu, Mar 5 - Mon, Mar 9
Delta Logo
7:35 pm - 6:50 am
PDX
-
BOS
8h 15m
1 stop
Delta Logo
6:44 pm - 11:54 pm
BOS
-
PDX
8h 10m
1 stop
$197Delta
Wed, Apr 1 - Wed, Apr 22
American Airlines Logo
11:59 pm - 11:38 am
PDX
-
BOS
8h 39m
1 stop
American Airlines Logo
3:59 pm - 11:41 pm
BOS
-
PDX
10h 42m
1 stop
$208American Airlines
Fri, Mar 27 - Wed, Apr 1
Delta Logo
5:36 pm - 6:50 am
PDX
-
BOS
10h 14m
1 stop
Delta Logo
6:15 am - 12:33 pm
BOS
-
PDX
9h 18m
1 stop
$217Delta
Tue, Mar 31 - Tue, Apr 7
Alaska Airlines Logo
1:35 pm - 11:59 pm
PDX
-
BOS
7h 24m
1 stop
Alaska Airlines Logo
6:00 am - 9:23 am
BOS
-
PDX
6h 23mnonstop
$227Alaska Airlines
Fri, Apr 3 - Tue, Apr 7
Alaska Airlines Logo
9:30 pm - 5:53 am
PDX
-
BOS
5h 23mnonstop
Alaska Airlines Logo
6:00 am - 9:23 am
BOS
-
PDX
6h 23mnonstop
$237Alaska Airlines
Wed, Mar 4 - Wed, Mar 11
United Airlines Logo
11:59 pm - 10:49 am
PDX
-
BOS
7h 50m
1 stop
United Airlines Logo
6:00 am - 1:44 pm
BOS
-
PDX
10h 44m
2 stops
$242United Airlines
Wed, Apr 22 - Tue, Apr 28
Southwest Logo
6:30 am - 10:10 pm
PDX
-
BDL
12h 40m
2 stops
Southwest Logo
11:20 am - 6:30 pm
BDL
-
PDX
10h 10m
2 stops
$369Southwest
Tue, Mar 3 - Sat, Mar 7
United Airlines Logo
1:18 pm - 11:49 pm
PDX
-
BDL
7h 31m
1 stop
United Airlines Logo
4:58 pm - 10:26 pm
BDL
-
PDX
8h 28m
1 stop
$372United Airlines
Tue, Mar 3 - Sat, Mar 7
Southwest Logo
6:30 am - 4:20 pm
PDX
-
BDL
6h 50m
1 stop
Southwest Logo
4:45 pm - 12:55 am
BDL
-
PDX
11h 10m
2 stops
$377Southwest
Tue, Jun 30 - Sat, Jul 4
JetBlue Logo
11:40 pm - 11:15 am
PDX
-
PVC
8h 35m
1 stop
JetBlue Logo
5:40 pm - 10:25 pm
PVC
-
PDX
7h 45m
1 stop
$920JetBlue
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.

What is the cheapest Portland to Massachusetts flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Massachusetts from Portland found in the last 72 hours was to Boston, at $251 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 72 hours was $251.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $266 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Massachusetts is May, when tickets cost $297 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $497 and $457 respectively.

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

The average price of all round-trip flights from Portland to Massachusetts clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Massachusetts on a Wednesday, 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 51% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 2% 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 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.

  • 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 $255 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 $486.

Reviews of the top 5 airlines serving from Portland to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Portland to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
Alaska AirlinesOverall score based on 11819 reviews
7.0Entertainment
8.1Boarding
8.5Crew
7.1Food
7.8Comfort
Airline reviews

Great. I did have a little issue getting into the Lounge, which is likely more an American Airlines issue. I did not carry my physical AAdvantage Executive credit card with me on this trip, which Admirals Club membership is a part of the benefits of having this card. The instructions on the AA website and the Citi cards website make it seem like you don't need the physical card, as both sites state you can enter with your boarding pass and driver's license. But both lounges said you were required to present the physical card (and not the digital version, via Apple Pay), as only the physical card says "Admirals Club" on the back.I also do not have a physical Admirals Club membership card, so while both lounges eventually let me in, both denied me entrance initially for this reason.

10.0 ExcellentWade, Jan 2026
PDX - LAX
Read more Alaska Airlines reviews

Great. I did have a little issue getting into the Lounge, which is likely more an American Airlines issue. I did not carry my physical AAdvantage Executive credit card with me on this trip, which Admirals Club membership is a part of the benefits of having this card. The instructions on the AA website and the Citi cards website make it seem like you don't need the physical card, as both sites state you can enter with your boarding pass and driver's license. But both lounges said you were required to present the physical card (and not the digital version, via Apple Pay), as only the physical card says "Admirals Club" on the back.I also do not have a physical Admirals Club membership card, so while both lounges eventually let me in, both denied me entrance initially for this reason.

Everything from the time I booked my flight through to the end when I got home was smooth and wonderful. Service was great, the flight attendants were attentive and there were no outstanding delays.

Delayed and no entertainment? I also forgot my headphones and immediately reported it and have not heard back yet.

The crew was very friendly. Boarding was quick and efficient.

You need categories to note when food and entertainment are not available. Alaska's system would not update flight info on the board for this flight, so there was some confusion after deplaning from the previous flight as to which gate and depart time were accurate for this flight.

we waited for 50 minutes to check a bag and missed a flight. do better.

The flight crew was very professional and pleasant. Our flight was delayed 3 hours, but Kayak informed me in advance

Before I even boarded this old white man , a fat Samoan lady, and a short brown guy were at the desk. They asked if we could have 15 volunteers to get free checked bags cause it was a full flight. I waited in line, I got up to the short brown guy and he asked for my boarding pass and I showed him, he said that he can’t check my bag because I wasn’t given a seat yet. So he had me go to the next line with the old white guy, but before I switched lines I asked him, well if I go to that line, will I be able to check my bag so I waited in line and he said yeah, it doesn’t matter , I’m good. So I switch lines and wait in the line of the old white man, with every guest before me he was very sweet , making small talk, smiling and had great eye contact( all of the people he was talking to was white) I come up and he doesn’t look at me , then says I’ll be right with you, I wait for him to initiate and when he does he’s like what’s up? I was like the man next to you told me I needed to get checked in before I can check my bag. He’s like what’s your last name and I say Valenzuela , and he said we’re not there yet, all while not smiling, no eye contact like he was with the other guests. He said we’re will call you when I get to you. So I go sit down and I’m sitting down for less than a minute and he calls me and someone else. I go up and say Valenzuela and he’s like who are you and I’m like Valenzuela , he’s like hmm and says don’t go anywhere and calls someone else. I finally get my seat and I go back to the short brown man and ask if I can check my bag and he said there isn’t any room available and I was like? Wait you told me and then the fat Samoan lady said yeah we don’t need anymore bags thank you. I was dumbfounded and just walked away. So rude. Terrible experience and terrible communication on their end.

The flight was delayed, but once it arrived everything moved right along.

Coke zero offered...good. The proptness of flight was late. This has been a everytime thing for my last 9 flights. And is putting alot of pressure on my connecting flights. Not a bit punctual. I am always early, but Ak. Airlines is not. And people i happen fly beside, parrot the same thing. The baggage delivery to baggage claim, is not prompt. Its slowwwww. The seats are poorly padded, very crowd. We need more room, not padding the airlines bottom line. Its like a cattle car. More leg room, more side to side room. And attendants need upgrade of verbal skills. I have been faithful to Ak. A., but it will change if changes are not made. Not the only planes in the sky.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

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!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

Unfortunately, I was put into the middle seat in the first row of premium seating. Sounds nice right? No! that is the worst seat in the plane. I wish I was in economy rather than be in that seat! There is no seat back pocket, no tray table, no charger. Nothing! so unless you're row mates are willing to let you share their basic amenities any flyer should have, you are stuck. It was the worst experience ever! And the flight attendant forgot to take my drink order. I felt like the forgotten flyer.

Delayed and cancelled flights were hard and very stressful, both ways!

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I had to cancel the flight because with a 3 hour delay for 'unexpected maintenance' in getting to LAX, I couldn't connect to an overseas flight that I had booked on Scandinavian Air.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

we were delayed because of some safety check that wasn't done or available

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Everything you need to know for your flight from Portland to Massachusetts

Information on your arrival and departure airports