$130 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 4/18. 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$219
Albany
Albany1 stop$375
Boston
Boston1 stop$219
Albany
Albany1 stop$375

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

Tue, Apr 21 - Tue, Apr 28
American Airlines Logo
11:47 pm - 10:39 am
PDX
-
BOS
7h 52m
1 stop
American Airlines Logo
3:16 pm - 10:56 pm
BOS
-
PDX
10h 40m
1 stop
$219American Airlines
Mon, Apr 27 - Mon, May 4
Southwest Logo
11:55 pm - 11:00 am
PDX
-
BOS
8h 05m
1 stop
Southwest Logo
3:45 pm - 12:55 am
BOS
-
PDX
12h 10m
2 stops
$224Southwest
Tue, Sep 1 - Sat, Sep 5
Delta Logo
11:39 am - 11:52 pm
PDX
-
BOS
9h 13m
1 stop
Delta Logo
11:15 am - 3:58 pm
BOS
-
PDX
7h 43m
1 stop
$239Delta
Sat, Jun 6 - Sat, Jun 13
JetBlue Logo
2:30 pm - 10:56 pm
PDX
-
BOS
5h 26mnonstop
JetBlue Logo
9:55 am - 1:04 pm
BOS
-
PDX
6h 09mnonstop
$257JetBlue
Mon, Aug 17 - Wed, Aug 26
Delta Logo
12:40 am - 1:27 pm
PDX
-
ACK
9h 47m
2 stops
Delta Logo
2:10 pm - 9:35 pm
ACK
-
PDX
10h 25m
1 stop
$346Delta
Sat, Aug 15 - Wed, Aug 19
JetBlue Logo
11:18 pm - 1:01 pm
PDX
-
ACK
10h 43m
1 stop
JetBlue Logo
3:43 pm - 10:23 pm
ACK
-
PDX
9h 40m
1 stop
$348JetBlue
Wed, May 27 - Tue, Jun 2
United Airlines Logo
11:30 pm - 9:45 am
PDX
-
BDL
7h 15m
1 stop
United Airlines Logo
4:50 pm - 10:30 pm
BDL
-
PDX
8h 40m
1 stop
$375United Airlines
Tue, Apr 14 - Tue, Apr 21
United Airlines Logo
2:30 pm - 12:53 am
PDX
-
ALB
7h 23m
1 stop
United Airlines Logo
4:55 pm - 10:34 pm
ALB
-
PDX
8h 39m
1 stop
$375United Airlines
Mon, Jun 1 - Wed, Jun 10
Multiple Airlines Logo
2:30 pm - 4:34 pm
PDX
-
EWB
23h 04m
2 stops
Multiple Airlines Logo
6:55 am - 1:04 pm
EWB
-
PDX
33h 09m
2 stops
$810Multiple Airlines
Mon, Jun 1 - Tue, Jun 9
Multiple Airlines Logo
2:30 pm - 4:34 pm
PDX
-
EWB
23h 04m
2 stops
Multiple Airlines Logo
7:40 am - 1:07 pm
EWB
-
PDX
32h 27m
2 stops
$825Multiple Airlines
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Massachusetts departing in April.

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 $227 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 $227.

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

The average price for all round-trip flights from Portland to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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 $485.

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 $286 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 $512 and $459 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 Tuesday, 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 48% 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$130
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 3% 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.

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.
7.9
Alaska AirlinesOverall score based on 12059 reviews
8.5Crew
7.8Comfort
7.0Food
7.0Entertainment
8.1Boarding
Airline reviews

Never got on because first part of trip was cancelled and we have no idea when we will get rebooked…

2.0 MediocreAnonymous, Mar 2026
PDX - SEA
Read more Alaska Airlines reviews

Never got on because first part of trip was cancelled and we have no idea when we will get rebooked…

Wonderful as always! Pleasant staff, smooth ride, and timely departure.

Everything ran like it should. Staff was professional. Looking forward to flying with them again.

Liked the attention and speed when getting wheelchair..........Was assured by phone that my needs would be taken care of and they were with my name.

The seats were spacious and comfortable. Even in basic economy. However, the flight boarded 30 minutes late.

Alaska used to be a top notch airline. With it's growth it is now in line with the big airlines. Not bad, not great.

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.

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

The crew were exceptionally nice and accommodating. My wife was tired after the flight from Haneda, Tokyo. They let her sleep and served her dinner later after she woke up, before we landed in PDX.

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

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.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

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

Information on your arrival and departure airports