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Cheap flights from Portland to Massachusetts from $108

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Massachusetts departing on 5/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Portland to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:43 pm - 6:49 am
PDX
-
BOS
8h 06m
1 stop
Delta Logo
6:45 pm - 11:59 pm
BOS
-
PDX
8h 14m
1 stop
$197Delta
Thu, Mar 12 - Sun, Mar 15
American Airlines Logo
11:59 pm - 11:38 am
PDX
-
BOS
8h 39m
1 stop
American Airlines Logo
4:38 pm - 11:53 pm
BOS
-
PDX
10h 15m
1 stop
$208American Airlines
Wed, Apr 1 - Wed, Apr 22
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
$217Alaska Airlines
Wed, Mar 18 - Tue, Mar 24
Delta Logo
1:53 pm - 11:50 pm
PDX
-
BOS
6h 57m
1 stop
Delta Logo
6:57 pm - 12:15 am
BOS
-
PDX
8h 18m
1 stop
$218Delta
Thu, Feb 26 - Mon, Mar 2
American Airlines Logo
11:48 am - 11:59 pm
PDX
-
BOS
9h 11m
1 stop
American Airlines Logo
12:32 pm - 8:44 pm
BOS
-
PDX
11h 12m
1 stop
$219American Airlines
Tue, Feb 24 - Tue, Mar 3
Hawaiian Airlines Logo
9:30 pm - 5:53 am
PDX
-
BOS
5h 23mnonstop
Hawaiian Airlines Logo
6:00 am - 9:23 am
BOS
-
PDX
6h 23mnonstop
$226Hawaiian Airlines
Thu, Mar 26 - Sat, Apr 4
Delta Logo
7:15 pm - 6:10 am
PDX
-
BOS
7h 55m
1 stop
Delta Logo
10:20 am - 4:01 pm
BOS
-
PDX
8h 41m
1 stop
$237Delta
Wed, Mar 18 - Tue, Mar 24
United Airlines Logo
11:59 pm - 10:50 am
PDX
-
BOS
7h 51m
1 stop
United Airlines Logo
6:00 am - 1:44 pm
BOS
-
PDX
10h 44m
2 stops
$242United Airlines
Tue, Mar 3 - Wed, Mar 11
United Airlines Logo
11:59 pm - 10:54 am
PDX
-
BDL
7h 55m
1 stop
United Airlines Logo
5:00 pm - 10:30 pm
BDL
-
PDX
8h 30m
1 stop
$359United Airlines
Wed, Apr 29 - Wed, May 6
JetBlue Logo
11:40 pm - 11:15 am
PDX
-
PVC
8h 35m
1 stop
JetBlue Logo
5:00 pm - 10:25 pm
PVC
-
PDX
8h 25m
1 stop
$1,185JetBlue
Thu, Jun 18 - Sun, Jun 21

United Airlines flights from Portland to Massachusetts

Our best United Airlines deals on Portland to Massachusetts flight tickets
United Airlines
Mar 3
PDX11:59 pmPortland
7h 51m
1 stop
BOS10:50 amBoston Logan Intl
Mar 11
BOS6:00 amBoston Logan Intl
10h 44m
2 stops
PDX1:44 pmPortland
$242
United Airlines
Feb 20
PDX10:38 pmPortland
7h 37m
1 stop
BOS9:15 amBoston Logan Intl
Feb 23
BOS1:55 pmBoston Logan Intl
9h 48m
1 stop
PDX8:43 pmPortland
$248
United Airlines
Jul 9
PDX10:40 pmPortland
7h 59m
1 stop
BOS9:39 amBoston Logan Intl
Jul 11
BOS6:35 pmBoston Logan Intl
8h 17m
1 stop
PDX11:52 pmPortland
$275

Southwest flights from Portland to Massachusetts

Our best Southwest deals on Portland to Massachusetts flight tickets
Southwest
Apr 29
PDX11:55 pmPortland
8h 00m
1 stop
BOS10:55 amBoston Logan Intl
May 5
BOS11:40 amBoston Logan Intl
12h 20m
2 stops
PDX9:00 pmPortland
$253
Southwest
Apr 1
PDX5:25 amPortland
6h 55m
1 stop
BOS3:20 pmBoston Logan Intl
Apr 8
BOS2:25 pmBoston Logan Intl
10h 35m
2 stops
PDX10:00 pmPortland
$264
Southwest
May 5
PDX6:30 amPortland
13h 10m
2 stops
BOS10:40 pmBoston Logan Intl
May 12
BOS2:25 pmBoston Logan Intl
11h 35m
2 stops
PDX11:00 pmPortland
$269

momondo Fare Finder

 
Customize your flight search to find flights from Portland to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 3/12

7:43 pm-6:49 am

1 stop8h 06m

Boston Logan Intl

Sun 3/15

6:45 pm-11:59 pm

1 stop8h 14m

$197

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 4/1

11:59 pm-11:38 am

1 stop8h 39m

Boston Logan Intl

Wed 4/22

4:38 pm-11:53 pm

1 stop10h 15m

$208

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 3/18

9:30 pm-5:53 am

Nonstop5h 23m

Boston Logan Intl

Tue 3/24

6:00 am-9:23 am

Nonstop6h 23m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 2/26

1:53 pm-11:50 pm

1 stop6h 57m

Boston Logan Intl

Mon 3/2

6:57 pm-12:15 am

1 stop8h 18m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 2/24

11:48 am-11:59 pm

1 stop9h 11m

Boston Logan Intl

Tue 3/3

12:32 pm-8:44 pm

1 stop11h 12m

$219

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 3/26

9:30 pm-5:53 am

Nonstop5h 23m

Boston Logan Intl

Sat 4/4

6:00 am-9:23 am

Nonstop6h 23m

$226

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 3/18

7:15 pm-6:10 am

1 stop7h 55m

Boston Logan Intl

Tue 3/24

10:20 am-4:01 pm

1 stop8h 41m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 3/3

11:59 pm-10:50 am

1 stop7h 51m

Boston Logan Intl

Wed 3/11

6:00 am-1:44 pm

2 stops10h 44m

$242

PortlandHartford

PDX - BDL

PDXBDL

Portland

Wed 4/29

11:59 pm-10:54 am

1 stop7h 55m

Hartford Bradley Intl

Wed 5/6

5:00 pm-10:30 pm

1 stop8h 30m

$359

PortlandProvincetown

PDX - PVC

PDXPVC

Portland

Thu 6/18

11:40 pm-11:15 am

1 stop8h 35m

Provincetown

Sun 6/21

5:00 pm-10:25 pm

1 stop8h 25m

$1,185

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Massachusetts from

How to get the cheapest flight ticket from Portland to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Massachusetts?

In general, May is the cheapest month to fly from Portland to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $297. If you aren’t able to travel to Massachusetts during the month of May, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $317.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Wednesday is the cheapest day to fly to Massachusetts from Portland. The lowest ticket price found for a Wednesday departure recently was $352. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Portland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $443.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Portland to Massachusetts flights are usually those with departure times at noon. Our users have found flights to Massachusetts at noon for as low as $255. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $486 on average. Flights to Massachusetts from Portland in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Portland to Massachusetts flight route?

Fly from Portland to Boston Logan Intl for the best Portland - Massachusetts flight prices

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $380 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Portland for as low as $274 on momondo.

What cabin class options are available on Portland to Massachusetts flights?

There are 4 cabin classes available to choose from on Portland to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Portland to Massachusetts flights?

You could potentially save up to 9% on your flight if you consider stops on a Portland to Massachusetts flight.

Cheap Portland to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Massachusetts

Best Price Found

$208

Fastest flight time

5h 20m

Direct flights

Every day

Airports in Massachusetts

140 airports
The best one-way flight to Massachusetts from Portland in the past 72 hours is $208. The best round-trip flight deal from Portland to Massachusetts found on momondo in the last 72 hours is $342.
The fastest flight from Portland to Massachusetts takes 5h 20m
Direct flights go from Portland to Massachusetts every day.
There are 140 airports in Massachusetts. From Portland there are direct flights to Boston Logan Intl (BOS).
Search flight deals

  • When did momondo last update prices for flights from Portland Airport to Massachusetts?

    Prices for flights from Portland Airport to Massachusetts are refreshed on a daily basis.

  • How many operators does momondo search for flights from Portland Airport to Massachusetts?

  • How old do you have to be to fly from Portland Airport to Massachusetts?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The necessary travel and health documents for your Massachusetts trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Portland to Massachusetts?

Best airlines flying from Portland to Massachusetts

Compare and see reviews for airlines that fly from Portland to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $108Free CancellationRating
7.9
8,147 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $108Free CancellationRating
7.8
2,831 reviews
Search Hawaiian Airlines flights
JetBluePriceFrom $108Free CancellationRating
7.2
2,893 reviews
Search JetBlue flights
American AirlinesPriceFrom $162Free CancellationRating
7.2
11,230 reviews
Search American Airlines flights
SouthwestPriceFrom $206Free CancellationRating
8.0
4,274 reviews
Search Southwest flights
United AirlinesPriceFrom $236Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $252Free CancellationRating
8.0
11,838 reviews
Search Alaska Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Massachusetts?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Portland to Massachusetts for you.

Can I find flights from Portland to Massachusetts with flexible booking policies on momondo?

Flights from Portland to Massachusetts with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Portland to Massachusetts?

Once all potential Portland to Massachusetts flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Portland to Massachusetts right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Portland to Massachusetts flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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