$108 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 9/13. 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

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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$216
Albany
Albany1 stop$325
Boston
Boston1 stop$216
Albany
Albany1 stop$325

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

Mon, Sep 15 - Sat, Sep 20
American Airlines Logo
6:07 am - 4:46 pmPDX-BOS
7h 39m1 stop
American Airlines Logo
5:00 am - 10:28 amBOS-PDX
8h 28m1 stop
$216American Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
American Airlines Logo
11:12 pm - 10:10 amPDX-BOS
7h 58m1 stop
American Airlines Logo
3:46 pm - 12:05 amBOS-PDX
11h 19m1 stop
$217American Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
Alaska Airlines Logo
1:24 pm - 12:27 amPDX-BOS
8h 03m1 stop
Alaska Airlines Logo
6:00 am - 9:09 amBOS-PDX
6h 09mnonstop
$227Alaska Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 7
Hawaiian Airlines Logo
1:24 pm - 12:27 amPDX-BOS
8h 03m1 stop
Hawaiian Airlines Logo
8:01 am - 4:50 pmBOS-PDX
11h 49m1 stop
$236Hawaiian Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 13
Delta Logo
5:06 pm - 6:25 amPDX-BOS
10h 19m1 stop
Delta Logo
8:10 am - 12:35 pmBOS-PDX
7h 25m1 stop
$237Delta
Find Deal
Tue, Sep 9 - Tue, Sep 16
Alaska Airlines Logo
7:33 am - 4:08 pmPDX-BOS
5h 35mnonstop
Alaska Airlines Logo
6:00 am - 9:09 amBOS-PDX
6h 09mnonstop
$247Alaska Airlines
Find Deal
Mon, Sep 15 - Sat, Sep 20
Hawaiian Airlines Logo
9:30 pm - 6:00 amPDX-BOS
5h 30mnonstop
Hawaiian Airlines Logo
7:45 am - 4:44 pmBOS-PDX
11h 59m1 stop
$251Hawaiian Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
Delta Logo
5:05 pm - 6:25 amPDX-BOS
10h 20m1 stop
Delta Logo
5:34 am - 12:39 pmBOS-PDX
10h 05m1 stop
$258Delta
Find Deal
Fri, Aug 29 - Sun, Aug 31
JetBlue Logo
12:21 pm - 8:43 pmPDX-BOS
5h 22mnonstop
JetBlue Logo
8:00 am - 11:11 amBOS-PDX
6h 11mnonstop
$262JetBlue
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Wed, Aug 13 - Wed, Aug 20
JetBlue Logo
11:35 pm - 7:55 amPDX-BOS
5h 20mnonstop
JetBlue Logo
8:00 am - 11:11 amBOS-PDX
6h 11mnonstop
$282JetBlue
Find Deal
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Portland to Massachusetts.

The cheapest ticket to Massachusetts from Portland found in the last 72 hours was to Boston, at $149 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 $149.

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 $717 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 February, when tickets cost $306 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $546 and $466 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 Thursday 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 49% 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$108
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 11% lower on average.
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 $513.

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from Portland to the following destinations at these prices or less: Boston $153 one-way - $278 round-trip

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 10000 reviews
8.1Boarding
7.1Food
7.1Entertainment
7.8Comfort
8.5Crew
Airline reviews

TERRIFIC! Thank you all. Jason Robert Kidwell My favorite flight attendants.

10.0 ExcellentJason, Jul 2025PDX - DCA
Read more Alaska Airlines reviews

TERRIFIC! Thank you all. Jason Robert Kidwell My favorite flight attendants.

I liked Alaska better than other carriers that I have EVER used. Unfortunately, the plane from LAX to Guanacaste leg of my journey had some mechanical problems and had to return to LAX - causing my journey to be very long and added a day to my total trip. The Airline was very prompt in offering their apology and have given me credit to use for my next flight. I thought the terminal in LAX was too cold for comfort, especially if there is a long wait between flights.

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

We have always flown with Alaska when we can. As they have great customer service. This trip we had to transfer to Air LINGUS in Denver to go to Dublin. That’s where things went bad! Our checked luggage didn’t arrive. The process to make a claim was way more complicated than it should be. It took 5 days to recover our luggage. The whole time we couldn’t talk to a real person who could tell us anything. The whole time Alaska blamed Air lingus and vis a versa. No one seemed want to help us. That was the worst part.

I'm a platinum member with American Airlines, however, my ticket did not display status and thus I did not board with an early group. I traveled with my two daughters and we were given a row of seats that did not recline. Not the treatment I would have expected for a platinum customer. The flight was also a bit late leaving Portland. Also on my flight to Portland we were not given premium seats. In fact, we were in the last row of the aircraft.

5 hour delay from Portland to Newark. Boarded and then were told we had to get off and wait five hours for flight. No food vouchers or any other compensation because they said it was an air traffic control issue. Plane is bare minimum like a discount airline. They have free entertainment but you have to get to it on your own device no screens in the seats

Very good. Gate personnel were excellent flight attendants were also able to change my seat at the last minute everyone, courteous, polite, and.

On time, smooth take off and landing, efficient boarding. Gate staff excellent, stewardess grumpy, but civil enough.

No WiFi available. It was too late to order food also. Guy next to me was huge (not fat) so had his shoulder & thigh next to me the whole way. Plane was delayed leaving PDX due to 8 other planes waiting. Not my best Alaska airlines flight.

Check in, they should have told me that upon arrival i needed to exit the secure area and re-check in with Eva Air. I wasn't sure what to do upon arrival at S.F.

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

The flight was supposed to leave at 7:30pm, but departed 10:50pm. They kept moving departure time out every half hour. It was a 45 minute flight from n Sunday night with great weather.

Flight got delayed and it was very inconvenient . Had to come with another carrier. Had to spend one more night in San Francisco.

Logging into next flight was an issue as I never received a confirmation code

Alaska airlines is not what I expected Very disappointed Unfriendly Discouraging Very bad customer service, heartbroken trying to explain to them my situation.

I could not check in ahead of time. Kayak did not give me a proper confirmation number to check in.

I loved flying Hawaiian Air! We didn’t pay to sit together, but we were able to anyway. They had usb charging ports and even outlets in some seats. They served a hot sandwich that was not very good, but we were still pleasantly surprised. The staff was very nice. The seats really made my booty hurt but maybe I’m just not used to sitting so long. Also, the AC was really cold even though I was wearing pants, a hoodie, and a light blanket.

A second drink service on a 6 hour flight would have been helpful.

The steward staff was particularly friendly and helpful. They smiled a lot and seemed anxious to be sure we enjoyed the flight.

Everything was good for the price I paid. Crew was very nice.

The worst flight experience I've ever had. Our flight was delayed 14 whole hours because the flight crew never showed up. We had to wait in a two hour line to get our new boarding passes, we were told we had no other option but to fly at 10pm (we didn't depart until 11:45pm). Everyone had to contact their hotels and car rental places, workplaces, etc. since we lost an entire day's worth of travel. The crew showed up at 10:15, which was past the time we were supposed to board. They were laughing and being completely smug when they boarded, and they took another hour to board us onto our flight. The flight crew never came to check in on us, we were quickly given one drink and sandwich and they turned off the lights and were negligent the rest of the trip. My mom asked three attendants for a seat belt extender, they never brought one. I was dehydrated and never received another drink. They were very rude and unfriendly, we had been up since 4am the morning of our flight and didn't land in our destination until 2am the next day (5am local time). This was unacceptable service and treatment, these flights are not cheap and we were inconvenienced out of an entire day of travel. This was 100% avoidable and was the fault of Hawaiian Airlines, and their crews inability to show up to work on time.

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

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