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Cheap flights from Portland to Massachusetts from $100

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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Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
11:40 pm - 8:00 amPDX-BOS
5h 20mnonstop
JetBlue Logo
7:05 pm - 10:25 pmBOS-PDX
6h 20mnonstop
$217JetBlue
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Fri, May 1 - Sat, May 9
Delta Logo
5:30 pm - 6:14 amPDX-BOS
9h 44m1 stop
Delta Logo
5:30 pm - 10:54 pmBOS-PDX
8h 24m1 stop
$218Delta
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Fri, Jan 16 - Sun, Jan 18
Southwest Logo
6:45 am - 10:05 pmPDX-BOS
12h 20m2 stops
Southwest Logo
5:30 am - 11:15 amBOS-PDX
8h 45m1 stop
$224Southwest
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Tue, Jan 6 - Sat, Jan 10
United Airlines Logo
11:19 pm - 12:33 pmPDX-BOS
10h 14m1 stop
United Airlines Logo
4:20 pm - 10:15 pmBOS-PDX
8h 55m1 stop
$237United Airlines
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Tue, Dec 2 - Mon, Dec 8
Delta Logo
5:45 pm - 6:32 amPDX-BOS
9h 47m1 stop
Delta Logo
1:45 pm - 10:22 pmBOS-PDX
11h 37m1 stop
$238Delta
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Mon, Feb 23 - Thu, Feb 26
United Airlines Logo
11:59 pm - 1:20 pmPDX-BOS
10h 21m2 stops
United Airlines Logo
12:45 pm - 6:56 pmBOS-PDX
9h 11m1 stop
$242United Airlines
Find Deal
Fri, Jan 16 - Sun, Jan 18
Alaska Airlines Logo
5:50 pm - 3:37 pmPDX-BOS
18h 47m1 stop
Alaska Airlines Logo
5:20 pm - 8:48 pmBOS-PDX
6h 28mnonstop
$294Alaska Airlines
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Mon, Dec 8 - Wed, Jan 7
Alaska Airlines Logo
5:50 pm - 3:37 pmPDX-BOS
18h 47m1 stop
Alaska Airlines Logo
5:20 pm - 8:48 pmBOS-PDX
6h 28mnonstop
$295Alaska Airlines
Find Deal
Wed, Dec 10 - Wed, Jan 7
Hawaiian Airlines Logo
7:04 am - 3:24 pmPDX-BOS
5h 20mnonstop
Hawaiian Airlines Logo
4:40 pm - 8:10 pmBOS-PDX
6h 30mnonstop
$326Hawaiian Airlines
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Fri, Dec 5 - Thu, Dec 11
Hawaiian Airlines Logo
7:04 am - 3:24 pmPDX-BOS
5h 20mnonstop
Hawaiian Airlines Logo
4:24 pm - 11:54 pmBOS-PDX
10h 30m1 stop
$331Hawaiian Airlines
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Fri, Dec 5 - Thu, Dec 11

Southwest flights from Portland to Massachusetts

Our best Southwest deals on Portland to Massachusetts flight tickets
Southwest
Jan 6
PDX6:45 amPortland
12h 20m
2 stops
BOS10:05 pmBoston Logan Intl
Jan 10
BOS5:30 amBoston Logan Intl
8h 45m
1 stop
PDX11:15 amPortland
$224
Find similar
Southwest
Dec 6
PDX6:00 amPortland
12h 55m
2 stops
BOS9:55 pmBoston Logan Intl
Dec 11
BOS1:35 pmBoston Logan Intl
8h 45m
1 stop
PDX7:20 pmPortland
$236
Find similar
Southwest
Dec 12
PDX6:30 amPortland
8h 10m
1 stop
BOS5:40 pmBoston Logan Intl
Dec 16
BOS2:10 pmBoston Logan Intl
11h 25m
2 stops
PDX10:35 pmPortland
$247
Find similar

United Airlines flights from Portland to Massachusetts

Our best United Airlines deals on Portland to Massachusetts flight tickets
United Airlines
Dec 2
PDX11:19 pmPortland
10h 14m
1 stop
BOS12:33 pmBoston Logan Intl
Dec 8
BOS4:20 pmBoston Logan Intl
8h 55m
1 stop
PDX10:15 pmPortland
$237
Find similar
United Airlines
Jan 16
PDX11:59 pmPortland
10h 21m
2 stops
BOS1:20 pmBoston Logan Intl
Jan 18
BOS12:45 pmBoston Logan Intl
9h 11m
1 stop
PDX6:56 pmPortland
$242
Find similar
United Airlines
Nov 15
PDX8:20 amPortland
7h 28m
1 stop
BOS6:48 pmBoston Logan Intl
Nov 18
BOS6:00 amBoston Logan Intl
8h 48m
1 stop
PDX11:48 amPortland
$259
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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 November 3, 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

Fri 5/1

11:40 pm-8:00 am

Nonstop5h 20m

Boston Logan Intl

Sat 5/9

7:05 pm-10:25 pm

Nonstop6h 20m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 1/16

5:30 pm-6:14 am

1 stop9h 44m

Boston Logan Intl

Sun 1/18

5:30 pm-10:54 pm

1 stop8h 24m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 1/6

6:45 am-10:05 pm

2 stops12h 20m

Boston Logan Intl

Sat 1/10

5:30 am-11:15 am

1 stop8h 45m

$224

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 12/2

11:19 pm-12:33 pm

1 stop10h 14m

Boston Logan Intl

Mon 12/8

4:20 pm-10:15 pm

1 stop8h 55m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 2/23

5:45 pm-6:32 am

1 stop9h 47m

Boston Logan Intl

Thu 2/26

1:45 pm-10:22 pm

1 stop11h 37m

$238

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 1/16

11:59 pm-1:20 pm

2 stops10h 21m

Boston Logan Intl

Sun 1/18

12:45 pm-6:56 pm

1 stop9h 11m

$242

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 12/8

5:50 pm-3:37 pm

1 stop18h 47m

Boston Logan Intl

Wed 1/7

5:20 pm-8:48 pm

Nonstop6h 28m

$294

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 12/10

5:50 pm-3:37 pm

1 stop18h 47m

Boston Logan Intl

Wed 1/7

5:20 pm-8:48 pm

Nonstop6h 28m

$295

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 12/5

7:04 am-3:24 pm

Nonstop5h 20m

Boston Logan Intl

Thu 12/11

4:40 pm-8:10 pm

Nonstop6h 30m

$326

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 12/5

7:04 am-3:24 pm

Nonstop5h 20m

Boston Logan Intl

Thu 12/11

4:24 pm-11:54 pm

1 stop10h 30m

$331

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, February 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 $309. If you aren’t able to travel to Massachusetts during the month of February, then flying in August 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 $360. 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, Monday 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 $262. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $515 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 $390 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 $296 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

1 airport
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 $427.
The fastest flight from Portland to Massachusetts takes 5h 20m
Direct flights go from Portland to Massachusetts every day.
There is 1 airport near Massachusetts: 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
2,799 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $129Free CancellationRating
7.9
8,001 reviews
Search Delta flights
JetBluePriceFrom $133Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
SouthwestPriceFrom $208Free CancellationRating
8.0
4,238 reviews
Search Southwest flights
United AirlinesPriceFrom $236Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $254Free CancellationRating
8.0
11,236 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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