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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 9/13. 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

American Airlines Logo
6:07 am - 4:46 pmPDX-BOS
7h 39m1 stop
American Airlines Logo
5:00 am - 10:28 amBOS-PDX
8h 28m1 stop
$216American Airlines
Find Deal
Mon, Sep 15 - Sat, Sep 20
American Airlines Logo
11:12 pm - 10:10 amPDX-BOS
7h 58m1 stop
American Airlines Logo
3:46 pm - 12:05 amBOS-PDX
11h 19m1 stop
$217American Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Alaska Airlines Logo
1:24 pm - 12:27 amPDX-BOS
8h 03m1 stop
Alaska Airlines Logo
6:00 am - 9:09 amBOS-PDX
6h 09mnonstop
$227Alaska Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
Hawaiian Airlines Logo
1:24 pm - 12:27 amPDX-BOS
8h 03m1 stop
Hawaiian Airlines Logo
8:01 am - 4:50 pmBOS-PDX
11h 49m1 stop
$236Hawaiian Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 7
Delta Logo
5:06 pm - 6:25 amPDX-BOS
10h 19m1 stop
Delta Logo
10:05 am - 4:10 pmBOS-PDX
9h 05m1 stop
$237Delta
Find Deal
Sat, Aug 30 - Wed, Sep 3
Alaska Airlines Logo
7:33 am - 4:08 pmPDX-BOS
5h 35mnonstop
Alaska Airlines Logo
6:00 am - 9:09 amBOS-PDX
6h 09mnonstop
$247Alaska Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
Hawaiian Airlines Logo
9:30 pm - 6:00 amPDX-BOS
5h 30mnonstop
Hawaiian Airlines Logo
7:45 am - 4:44 pmBOS-PDX
11h 59m1 stop
$251Hawaiian Airlines
Find Deal
Mon, Sep 15 - Sat, Sep 20
Delta Logo
5:05 pm - 6:25 amPDX-BOS
10h 20m1 stop
Delta Logo
5:34 am - 12:39 pmBOS-PDX
10h 05m1 stop
$258Delta
Find Deal
Thu, Sep 4 - Mon, Sep 8
JetBlue Logo
12:21 pm - 8:43 pmPDX-BOS
5h 22mnonstop
JetBlue Logo
8:00 am - 11:11 amBOS-PDX
6h 11mnonstop
$262JetBlue
Find Deal
Fri, Aug 29 - Sun, Aug 31
JetBlue Logo
11:35 pm - 7:55 amPDX-BOS
5h 20mnonstop
JetBlue Logo
8:00 am - 11:11 amBOS-PDX
6h 11mnonstop
$282JetBlue
Find Deal
Wed, Aug 13 - Wed, Aug 20

Delta flights from Portland to Massachusetts

Our best Delta deals on Portland to Massachusetts flight tickets
Delta
Aug 30
PDX5:06 pmPortland
10h 19m
1 stop
BOS6:25 amBoston Logan Intl
Sep 3
BOS10:05 amBoston Logan Intl
9h 05m
1 stop
PDX4:10 pmPortland
$237
Find similar
Delta
Sep 4
PDX5:05 pmPortland
10h 20m
1 stop
BOS6:25 amBoston Logan Intl
Sep 8
BOS5:34 amBoston Logan Intl
10h 05m
1 stop
PDX12:39 pmPortland
$258
Find similar
Delta
Sep 5
PDX11:50 amPortland
9h 04m
1 stop
BOS11:54 pmBoston Logan Intl
Sep 10
BOS5:15 amBoston Logan Intl
8h 25m
1 stop
PDX10:40 amPortland
$268
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Southwest flights from Portland to Massachusetts

Our best Southwest deals on Portland to Massachusetts flight tickets
Southwest
Sep 8
PDX9:05 pmPortland
8h 05m
1 stop
BOS8:10 amBoston Logan Intl
Sep 20
BOS9:10 amBoston Logan Intl
10h 15m
1 stop
PDX4:25 pmPortland
$248
Find similar
Southwest
Sep 29
PDX6:10 amPortland
10h 55m
1 stop
BOS8:05 pmBoston Logan Intl
Oct 6
BOS6:50 pmBoston Logan Intl
8h 05m
1 stop
PDX11:55 pmPortland
$263
Find similar
Southwest
Sep 15
PDX9:05 pmPortland
10h 25m
1 stop
BOS10:30 amBoston Logan Intl
Sep 29
BOS5:15 amBoston Logan Intl
7h 45m
1 stop
PDX10:00 amPortland
$272
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 July 31, 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

Mon 9/15

6:07 am-4:46 pm

1 stop7h 39m

Boston Logan Intl

Sat 9/20

5:00 am-10:28 am

1 stop8h 28m

$216

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 9/2

11:12 pm-10:10 am

1 stop7h 58m

Boston Logan Intl

Tue 9/9

3:46 pm-12:05 am

1 stop11h 19m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 9/9

1:24 pm-12:27 am

1 stop8h 03m

Boston Logan Intl

Tue 9/16

6:00 am-9:09 am

Nonstop6h 09m

$227

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 9/30

1:24 pm-12:27 am

1 stop8h 03m

Boston Logan Intl

Tue 10/7

8:01 am-4:50 pm

1 stop11h 49m

$236

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 8/30

5:06 pm-6:25 am

1 stop10h 19m

Boston Logan Intl

Wed 9/3

10:05 am-4:10 pm

1 stop9h 05m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 9/9

7:33 am-4:08 pm

Nonstop5h 35m

Boston Logan Intl

Tue 9/16

6:00 am-9:09 am

Nonstop6h 09m

$247

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 9/15

9:30 pm-6:00 am

Nonstop5h 30m

Boston Logan Intl

Sat 9/20

7:45 am-4:44 pm

1 stop11h 59m

$251

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 9/4

5:05 pm-6:25 am

1 stop10h 20m

Boston Logan Intl

Mon 9/8

5:34 am-12:39 pm

1 stop10h 05m

$258

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 8/29

12:21 pm-8:43 pm

Nonstop5h 22m

Boston Logan Intl

Sun 8/31

8:00 am-11:11 am

Nonstop6h 11m

$262

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 8/13

11:35 pm-7:55 am

Nonstop5h 20m

Boston Logan Intl

Wed 8/20

8:00 am-11:11 am

Nonstop6h 11m

$282

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 $306. If you aren’t able to travel to Massachusetts during the month of February, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $307.

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 $343. 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 $455.

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 $513 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 $388 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 $278 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 5% 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

$108

Fastest flight time

5h 20m

Direct flights

Every day

Airports in Massachusetts

4 airports
The best one-way flight to Massachusetts from Portland in the past 72 hours is $108. The best round-trip flight deal from Portland to Massachusetts found on momondo in the last 72 hours is $216.
The fastest flight from Portland to Massachusetts takes 5h 20m
Direct flights go from Portland to Massachusetts every day.
There are 4 airports near Massachusetts: Boston Logan Intl (BOS), Albany Intl (ALB), Nantucket Memorial (ACK), Hartford Bradley Intl (BDL)
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  • 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
Spirit AirlinesPriceFrom $73Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
Hawaiian AirlinesPriceFrom $122Free CancellationRating
7.8
2,611 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $130Free CancellationRating
8.0
7,981 reviews
Search Delta flights
JetBluePriceFrom $150Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
American AirlinesPriceFrom $162Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Sun Country AirPriceFrom $180Free CancellationRating
6.9
334 reviews
Search Sun Country Air flights
SouthwestPriceFrom $216Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $236Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $255Free CancellationRating
8.0
10,000 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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