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Cheap flights from Portland to Massachusetts from $99

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 1/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
American Airlines Logo
10:15 pm - 10:29 am
PDX
-
BOS
9h 14m1 stop
American Airlines Logo
9:45 am - 6:51 pm
BOS
-
PDX
12h 06m1 stop
$208American Airlines
Tue, Jan 6 - Tue, Jan 20
Delta Logo
5:05 pm - 6:09 am
PDX
-
BOS
10h 04m1 stop
Delta Logo
6:35 pm - 11:53 pm
BOS
-
PDX
8h 18m1 stop
$218Delta
Sat, May 23 - Tue, May 26
American Airlines Logo
10:15 pm - 10:29 am
PDX
-
BOS
9h 14m1 stop
American Airlines Logo
6:00 am - 1:41 pm
BOS
-
PDX
10h 41m1 stop
$219American Airlines
Tue, Jan 6 - Sat, Jan 10
Southwest Logo
6:20 am - 8:50 pm
PDX
-
BOS
11h 30m2 stops
Southwest Logo
5:30 am - 11:15 am
BOS
-
PDX
8h 45m1 stop
$224Southwest
Tue, Jan 6 - Sat, Jan 10
Alaska Airlines Logo
7:00 am - 3:20 pm
PDX
-
BOS
5h 20mnonstop
Alaska Airlines Logo
5:20 pm - 8:48 pm
BOS
-
PDX
6h 28mnonstop
$227Alaska Airlines
Thu, Jan 22 - Wed, Jan 28
United Airlines Logo
11:05 pm - 11:12 am
PDX
-
BOS
9h 07m1 stop
United Airlines Logo
11:17 am - 6:10 pm
BOS
-
PDX
9h 53m1 stop
$237United Airlines
Tue, Jan 6 - Tue, Jan 20
United Airlines Logo
5:00 am - 3:37 pm
PDX
-
BOS
7h 37m1 stop
United Airlines Logo
2:20 pm - 10:32 pm
BOS
-
PDX
11h 12m2 stops
$242United Airlines
Thu, Jan 22 - Mon, Jan 26
Southwest Logo
6:30 am - 4:15 pm
PDX
-
ALB
6h 45m1 stop
Southwest Logo
5:15 am - 10:45 am
ALB
-
PDX
8h 30m1 stop
$373Southwest
Tue, Jan 6 - Thu, Jan 15
JetBlue Logo
11:40 pm - 11:02 am
PDX
-
HYA
8h 22m1 stop
JetBlue Logo
2:03 pm - 10:25 pm
HYA
-
PDX
11h 22m1 stop
$1,145JetBlue
Sat, May 16 - Sat, Jun 6
JetBlue Logo
11:40 pm - 11:02 am
PDX
-
HYA
8h 22m1 stop
JetBlue Logo
1:55 pm - 10:25 pm
HYA
-
PDX
11h 30m1 stop
$1,205JetBlue
Sat, May 16 - Fri, Jun 5

American Airlines flights from Portland to Massachusetts

Our best American Airlines deals on Portland to Massachusetts flight tickets
American Airlines
Jan 6
PDX10:15 pmPortland
9h 14m
1 stop
BOS10:29 amBoston Logan Intl
Jan 20
BOS9:45 amBoston Logan Intl
12h 06m
1 stop
PDX6:51 pmPortland
$208
Find similar
American Airlines
Jan 6
PDX10:15 pmPortland
9h 14m
1 stop
BOS10:29 amBoston Logan Intl
Jan 13
BOS12:55 pmBoston Logan Intl
10h 32m
1 stop
PDX8:27 pmPortland
$219
Find similar
American Airlines
Apr 1
PDX11:46 amPortland
8h 37m
1 stop
BOS11:23 pmBoston Logan Intl
Apr 22
BOS3:45 pmBoston Logan Intl
10h 52m
1 stop
PDX11:37 pmPortland
$236
Find similar

Delta flights from Portland to Massachusetts

Our best Delta deals on Portland to Massachusetts flight tickets
Delta
May 23
PDX5:05 pmPortland
10h 04m
1 stop
BOS6:09 amBoston Logan Intl
May 26
BOS6:35 pmBoston Logan Intl
8h 18m
1 stop
PDX11:53 pmPortland
$218
Find similar
Delta
Jan 1
PDX5:30 amPortland
7h 33m
1 stop
BOS4:03 pmBoston Logan Intl
Jan 14
BOS12:45 pmBoston Logan Intl
10h 50m
1 stop
PDX8:35 pmPortland
$241
Find similar
Delta
Jan 7
PDX5:50 amPortland
13h 03m
2 stops
BOS9:53 pmBoston Logan Intl
Jan 18
BOS7:30 amBoston Logan Intl
11h 55m
1 stop
PDX4:25 pmPortland
$265
Find similar

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 December 18, 2025.
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

Tue 1/6

10:15 pm-10:29 am

1 stop9h 14m

Boston Logan Intl

Tue 1/20

9:45 am-6:51 pm

1 stop12h 06m

$208

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 5/23

5:05 pm-6:09 am

1 stop10h 04m

Boston Logan Intl

Tue 5/26

6:35 pm-11:53 pm

1 stop8h 18m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 1/6

10:15 pm-10:29 am

1 stop9h 14m

Boston Logan Intl

Sat 1/10

6:00 am-1:41 pm

1 stop10h 41m

$219

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 1/6

6:20 am-8:50 pm

2 stops11h 30m

Boston Logan Intl

Sat 1/10

5:30 am-11:15 am

1 stop8h 45m

$224

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 1/22

7:00 am-3:20 pm

Nonstop5h 20m

Boston Logan Intl

Wed 1/28

5:20 pm-8:48 pm

Nonstop6h 28m

$227

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 1/6

11:05 pm-11:12 am

1 stop9h 07m

Boston Logan Intl

Tue 1/20

11:17 am-6:10 pm

1 stop9h 53m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 1/22

5:00 am-3:37 pm

1 stop7h 37m

Boston Logan Intl

Mon 1/26

2:20 pm-10:32 pm

2 stops11h 12m

$242

PortlandAlbany

PDX - ALB

PDXALB

Portland

Tue 1/6

6:30 am-4:15 pm

1 stop6h 45m

Albany Intl

Thu 1/15

5:15 am-10:45 am

1 stop8h 30m

$373

PortlandHyannis

PDX - HYA

PDXHYA

Portland

Sat 5/16

11:40 pm-11:02 am

1 stop8h 22m

Hyannis Barnstable

Sat 6/6

2:03 pm-10:25 pm

1 stop11h 22m

$1,145

PortlandHyannis

PDX - HYA

PDXHYA

Portland

Sat 5/16

11:40 pm-11:02 am

1 stop8h 22m

Hyannis Barnstable

Fri 6/5

1:55 pm-10:25 pm

1 stop11h 30m

$1,205

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 January is also cheap. Prices for this month can be found on momondo for an average of $298.

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 $359. 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 $435.

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 $262. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $503 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 $383 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 $279 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 17% 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

$193

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 $193. The best round-trip flight deal from Portland to Massachusetts found on momondo in the last 72 hours is $417.
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
Hawaiian AirlinesPriceFrom $122Free CancellationRating
7.8
2,819 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $124Free CancellationRating
7.9
8,005 reviews
Search Delta flights
JetBluePriceFrom $128Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
Sun Country AirPriceFrom $158Free CancellationRating
6.9
333 reviews
Search Sun Country Air flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
SouthwestPriceFrom $206Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
United AirlinesPriceFrom $236Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $255Free CancellationRating
8.0
11,477 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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