$110 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 5/13. 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$203
Albany
Albany1 stop$339
Boston
Boston1 stop$203
Albany
Albany1 stop$339

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

Sun, Jan 11 - Fri, Jan 16
United Airlines Logo
11:05 pm - 11:12 am
PDX
-
BOS
9h 07m1 stop
United Airlines Logo
5:57 pm - 12:31 am
BOS
-
PDX
9h 34m1 stop
$203United Airlines
Mon, Feb 16 - Sat, Feb 21
American Airlines Logo
12:59 am - 3:06 pm
PDX
-
BOS
11h 07m1 stop
American Airlines Logo
2:01 pm - 9:22 pm
BOS
-
PDX
10h 21m1 stop
$208American Airlines
Thu, Jan 1 - Wed, Jan 14
Delta Logo
5:30 am - 4:03 pm
PDX
-
BOS
7h 33m1 stop
Delta Logo
7:30 am - 4:25 pm
BOS
-
PDX
11h 55m1 stop
$218Delta
Wed, Jan 7 - Mon, Jan 12
Southwest Logo
6:20 am - 8:50 pm
PDX
-
BOS
11h 30m2 stops
Southwest Logo
4:50 pm - 10:15 pm
BOS
-
PDX
8h 25m1 stop
$224Southwest
Wed, Mar 11 - Wed, Mar 18
Delta Logo
7:38 pm - 6:49 am
PDX
-
BOS
8h 11m1 stop
Delta Logo
11:10 am - 6:58 pm
BOS
-
PDX
10h 48m1 stop
$228Delta
Thu, Jan 29 - Sun, Feb 1
American Airlines Logo
6:00 am - 4:43 pm
PDX
-
BOS
7h 43m1 stop
American Airlines Logo
11:21 am - 8:24 pm
BOS
-
PDX
12h 03m1 stop
$236American Airlines
Sat, Apr 18 - Tue, Apr 21
United Airlines Logo
2:10 pm - 1:06 am
PDX
-
BOS
7h 56m1 stop
United Airlines Logo
6:00 am - 11:42 am
BOS
-
PDX
8h 42m1 stop
$237United Airlines
Thu, Jan 22 - Sun, Jan 25
United Airlines Logo
8:30 am - 9:52 pm
PDX
-
BOS
10h 22m2 stops
United Airlines Logo
6:00 am - 11:57 am
BOS
-
PDX
8h 57m1 stop
$242United Airlines
Thu, Jan 15 - Sun, Jan 25
American Airlines Logo
10:15 pm - 10:31 am
PDX
-
BOS
9h 16m1 stop
American Airlines Logo
1:48 pm - 8:24 pm
BOS
-
PDX
9h 36m1 stop
$253American Airlines
Wed, Jan 21 - Sat, Jan 24
Southwest Logo
6:30 am - 4:20 pm
PDX
-
BDL
6h 50m1 stop
Southwest Logo
9:50 am - 7:45 pm
BDL
-
PDX
12h 55m2 stops
$368Southwest
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 $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 72 hours was $297.

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 $301 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 $547 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 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$110
Best time to beat the crowds with an average 19% 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 $262 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 $503.

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 11429 reviews
8.5Crew
7.1Food
7.8Comfort
8.1Boarding
7.0Entertainment
Airline reviews

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

8.0 ExcellentAnonymous, Dec 2025
PDX - PHX
Read more Alaska Airlines reviews

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

The food selections were not good, and entertainment was non existent.

I would have liked if the flight existed. To be fair the federal government canceled it. But, since it WAS canceled, I would have liked it if Alaska Airlines had moved a finger to assist me rather then abandoning me with my luggage, unable to check it, for 14 hours in Portland. So federal regulations forbid them from storing my bag? Then at least help me find storage or SOMETHING.

It was all good, no delays which was a worry. All great

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

This was more with the third party booking through Kayak but my KTN for Pre-TSA, even though I entered it, wasn't assigned to my ticket when I got to the airport. I had to go through regular security. Also the Alaska app had trouble loading my ticket in the first place and I had to ask for it to be printed. Alaska Airlines was great but wanted you to know about this hiccup in the ticketing interface.

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

When I bought my tickets I up great my seats for extra $104 each seats 8A and 8B in the way back from Portland to Palm Springs they gave me the seats 15. I thought it was for round trip same seats . So I was very disappointed ☹️

One disappointment. There was a gate change from B8 to B10, they had announced it maybe 20 minutes before the boarding time, possibly less. I didn’t hear the announcement as I was listening to music on my head phones at B8. At the boarding time, I got up and asked the gal at the B8 boarding desk, why the destination sign had not changed and if the flight was delayed as there was no plane behind her through the window, she said that perhaps the flight was delayed and the screen will probably update in -5 minutes ( she apparently didn’t know the boarding gate was changed ( 2 down from our location) I put my headphones on and went back to sit down . Just before the B10 door closed, I got a phone call asking me if I was still taking the flight, I said. “Yes” but I was at the gate stated on my ticket B8, then I was informed of the gate change, I got up and ran to the gate, and down the hallway to the jet ramp. I was the last to board!! Very frustrating . I was shocked that I got no emails or text messages from Alaska informing me of a last minute change!!

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

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.

The flight was CANCELED!!! Can’t get much more “poor” than that. I had to switch to American Airlines, add another layover and got home in Honolulu 4 hours later than I was supposed to be home. One bright spot was Josh with Alaska Airlines at SFO. He got me on a United Flight that got me home a few hours before I would have. Without him I would have gotten home almost 7 hours after my originally scheduled flight.

Canceled my flight within 24 hours, causing me arriving home midnight. Will never book Hawaiian airlines anymore

I like Hawaiian, it was great that they had good internet connection across the Pacific Ocean, thanks to Star Link satellites. The seating was comfortable, ( I was in economy ). Maybe I missed it, but I only got offered a beverage once. It was a nonstop flight KOA to SMF. I would take it again next time I go that way.

I always love flying Hawaii and I have nothing to add

Previously flown Hawaiian Airlines on similar routes, I found Alaska Airlines to be noticeably more comfortable. The seats on Alaska Airlines provided better support and cushioning, which made a significant difference on the long flight to the islands. When you’re spending 5-6 hours in the air, seat comfort really matters, and Alaska Airlines delivered where it counts. After comparing both carriers, I’ve decided to book with Alaska Airlines for all my future Hawaii trips. The superior seat comfort alone makes it worth choosing Alaska over Hawaiian Airlines. If you’re planning a trip to Hawaii and prioritizing comfort, I’d recommend giving Alaska Airlines a try. You won’t be disappointed. Highly recommended for Hawaii travel!

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

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.

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

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

Information on your arrival and departure airports