$99 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 7/9. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

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

Best Massachusetts Flight Deals from Portland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$197
Albany
Albany1 stop$297
Boston
Bostonnonstop$197
Albany
Albany1 stop$297

Cheap Flights from Portland to Massachusetts

 
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

Tue, Jul 15 - Wed, Jul 23
JetBlue Logo
11:40 pm - 8:00 amPDX-BOS
5h 20mnonstop
JetBlue Logo
6:55 pm - 10:15 pmBOS-PDX
6h 20mnonstop
$197JetBlue
Find Deal
Thu, Jul 24 - Tue, Jul 29
JetBlue Logo
11:40 pm - 8:00 amPDX-BOS
5h 20mnonstop
JetBlue Logo
6:55 pm - 10:15 pmBOS-PDX
6h 20mnonstop
$207JetBlue
Find Deal
Wed, Sep 10 - Sat, Sep 13
Delta Logo
1:46 pm - 12:19 amPDX-BOS
7h 33m1 stop
Delta Logo
8:05 am - 4:07 pmBOS-PDX
11h 02m1 stop
$217Delta
Find Deal
Fri, Jul 25 - Wed, Jul 30
Alaska Airlines Logo
5:30 pm - 7:30 amPDX-BOS
11h 00m1 stop
Alaska Airlines Logo
6:32 pm - 11:59 pmBOS-PDX
8h 27m1 stop
$226Alaska Airlines
Find Deal
Mon, Aug 18 - Sat, Aug 23
Delta Logo
10:05 pm - 9:37 amPDX-BOS
8h 32m1 stop
Delta Logo
6:10 am - 12:13 pmBOS-PDX
9h 03m1 stop
$227Delta
Find Deal
Sun, Aug 17 - Wed, Aug 20
United Airlines Logo
11:59 pm - 10:59 amPDX-BOS
8h 00m1 stop
United Airlines Logo
5:05 pm - 10:42 pmBOS-PDX
8h 37m1 stop
$237United Airlines
Find Deal
Tue, Aug 12 - Tue, Aug 19
Hawaiian Airlines Logo
9:37 pm - 6:00 amPDX-BOS
5h 23mnonstop
Hawaiian Airlines Logo
8:40 am - 4:49 pmBOS-PDX
11h 09m1 stop
$267Hawaiian Airlines
Find Deal
Fri, Jul 11 - Tue, Jul 15
Alaska Airlines Logo
9:37 pm - 6:00 amPDX-BOS
5h 23mnonstop
Alaska Airlines Logo
8:19 pm - 9:45 amBOS-PDX
16h 26m1 stop
$272Alaska Airlines
Find Deal
Mon, Oct 13 - Fri, Oct 17
United Airlines Logo
6:25 pm - 6:00 amPDX-BOS
8h 35m1 stop
United Airlines Logo
5:05 pm - 10:45 pmBOS-PDX
8h 40m1 stop
$285United Airlines
Find Deal
Sat, Jul 12 - Mon, Jul 21
Hawaiian Airlines Logo
9:37 pm - 6:00 amPDX-BOS
5h 23mnonstop
Hawaiian Airlines Logo
6:00 am - 9:17 amBOS-PDX
6h 17mnonstop
$327Hawaiian Airlines
Find Deal
Useful Info

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 $108 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 $108.

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.

No, with an average price for the route of $332, prices are generally cheapest when you fly direct.

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 September, when tickets cost $307 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $547 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. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.


Good to know

Low seasonFebruary
High seasonAugust
Cheapest flight$99
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 8% 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 $528.

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 - $226 round-trip

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

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

10.0 Excellentmarlene, Jun 2025PDX - SMF
Read more Alaska Airlines reviews

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.

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.

Flight last minute delayed 2 hours for crew calling out sick

Husband was new to the wheelchair accommodations this trip. What a blessing that was. All employees were helpful and customer service was excellent

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

Laney was very helpful. I am computer illiterate. She helped me obtain a boarding pass and preferred seat. She was warm, friendly, helpful, and smiled. I was impressed.

The actual flight I was rescheduled onto was from Seattle to Bozeman. The flight itself was fine, but due to delays/air traffic issues i spent the day hanging out at the Seattle airport and had to miss a day of work.

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Flight was canceled with no voucher of any kind and next available flight was two days later.

Boarding was chaotic. Microphone not working properly and second agent was distracted from task with baggage and late arrivals.

I DID NOT GO TO HAWAII ON HAWAIIAN AIRLINES. YOU DID NOT INFORM ME THAT BY CHOOSING BASIC ECONOMY, I MIGHT BE REQUIRED TO FLY STANDBY. I AM ELDERLY AS WAS MY COMPANION WHO IS ALSO SEVERELY DISABLED AND THERE WOULD BE NO WAY WE COULD TRAVEL ON STANDBY. THEY TOLD ME THAT ALL OF THE BASIC ECONOMY SEATS HAD BEEN SELECTED BY OTHER PASSENGERS AND WE HAD TO PAY AN ADDITIONAL $942 TO GET A SECURED SEAT ON THE PLAN AND, IN SPITE OF THE ADDITIONAL COST, WE WERE NOT ALLOW US TO AMEND OUR TRAVEL PLANS TO EXTEND OUR VACATION. ULTIMATELY, THE FLIGHT WAS DELAYED. WE WERE OFFERED A REFUND IF WE CANCELED OUR TRIP ALTOGETHER WHICH WE DID. IT IS YOUR DUTY TO INFORM YOUR CUSTOMERS OF THE POTENTIAL PROBLEMS THEY MAY FACE, AND YOU DID NOT DO SO. I WILL NOT UTILIZE YOUR SERVICES EVER AGAIN.

It was very pleasant. The staff and crew are very polite.

On time. Alaska upgraded seat comfort with memory foam seat covers with head rests

the people at the counter, NEED TO BE MORE HELPFUL. we had three suitcases to check in and we were not trying to be an INCONVENIENCE TO YOUR clerks. but she was not helpful and made our trip back home memorable but not IN A GOOD WAY. Sadly to say, you guys need to teach to be and to go above and beyond to help THE CUSTOMER BY ANY MEANS POSSIBLE. they need to leave aside whatever they are going thru in their lives, THEIR WORK DEMANDS THAT OF THEM, IF NOT THEY ARE NOT IN THE JOB THEY SUPPOSED TO.

Because the airport is under construction and because Hawaiian air just changed terminals we missed boarding out flight by 5 minutes. That cost me a night in an airport hotel and several hours of rebooking to make it to my destination. Costumers need to know that airport construction is a problem and they need to add an hour to deal with the air train delays from Federal Circle.

Half of my family members didn’t make it because they involuntary bumped off . And their seats where given away

Hawaiian Airlines staff is always professional & quick & easy check in & boarding process

Customer service by Susan of Alaskan Air was outstanding. We missed our flight out of JFK. She got us rebooked the following day. Way to go Susan.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

Smooth flight, especially take off and landing, and great crew on board. Really loved the stroopwaffles!

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

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