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Massachusetts

$100+ Cheap flights from Portland (PDX) to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Portland to Massachusetts

Cheapest flights from Portland to Massachusetts
Explore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:38 pm
PDX
-
BOS
1 stop7h 45m
Delta
Tue 6/26:35 pm
BOS
-
PDX
1 stop8h 18m
Delta
Deal found 1/20$199
This American Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/111:59 pm
PDX
-
BOS
1 stop8h 39m
American Airlines
Wed 4/223:59 pm
BOS
-
PDX
1 stop10h 42m
American Airlines
Deal found 1/19$208
This Alaska Airlines deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:37 pm
PDX
-
BOS
Nonstop5h 25m
Alaska Airlines
Tue 8/256:00 am
BOS
-
PDX
Nonstop6h 19m
Alaska Airlines
Deal found 1/21$217
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/165:36 pm
PDX
-
BOS
1 stop10h 14m
Delta
Tue 3/317:10 am
BOS
-
PDX
1 stop9h 01m
Delta
Deal found 1/20$218
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:30 am
PDX
-
BOS
1 stop7h 29m
Delta
Wed 3/114:54 pm
BOS
-
PDX
1 stop7h 59m
Delta
Deal found 1/20$219
This Delta deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:39 am
PDX
-
BOS
1 stop9h 13m
Delta
Fri 8/283:30 pm
BOS
-
PDX
1 stop8h 19m
Delta
Deal found 1/21$229
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/39:30 pm
PDX
-
BOS
Nonstop5h 23m
Hawaiian Airlines
Tue 4/76:00 am
BOS
-
PDX
Nonstop6h 23m
Hawaiian Airlines
Deal found 1/20$233
This American Airlines deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:59 pm
PDX
-
BOS
1 stop8h 34m
American Airlines
Wed 5/65:43 pm
BOS
-
PDX
1 stop8h 58m
American Airlines
Deal found 1/21$235
This Alaska Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:00 am
PDX
-
BOS
Nonstop5h 27m
Alaska Airlines
Mon 4/136:00 am
BOS
-
PDX
Nonstop6h 23m
Alaska Airlines
Deal found 1/20$237
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:15 pm
PDX
-
BOS
1 stop7h 55m
Delta
Sat 3/215:15 pm
BOS
-
PDX
1 stop8h 38m
Delta
Deal found 1/20$238
This American Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/139:44 pm
PDX
-
BOS
1 stop9h 21m
American Airlines
Thu 2/195:31 pm
BOS
-
PDX
1 stop9h 46m
American Airlines
Deal found 1/19$239
This United Airlines deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:38 pm
PDX
-
BOS
1 stop7h 37m
United Airlines
Wed 2/256:00 am
BOS
-
PDX
2 stops10h 44m
United Airlines
Deal found 1/21$242

Find flight deals from Portland to Massachusetts

Keep the following information in mind while searching for Portland to Massachusetts flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$199
(Delta)

One-way from

$100
(Delta)

Popular in

December

Cheapest in

May

Average price

$337

Good round-trip deal

$337 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Portland-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Boston Logan Intl flights.
Search Deals
From Portland to Massachusetts
Search Deals
One-way flight from Portland to Massachusetts
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Portland to Massachusetts.
Search Deals
Price to beat on a one-way flight from Portland to Massachusetts.
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.

Fly from

Portland

Fly to

Massachusetts

Route

Depart

Return

Price

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 2/16

7:35 pm-6:50 am

1 stop8h 15m

Boston Logan Intl

Mon 2/23

6:57 pm-12:15 am

1 stop8h 18m

$199

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 2/2

5:08 pm-6:05 am

1 stop9h 57m

Boston Logan Intl

Mon 2/9

12:45 pm-10:20 pm

1 stop12h 35m

$243

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sun 4/12

9:30 pm-5:53 am

Nonstop5h 23m

Boston Logan Intl

Wed 4/15

4:27 pm-7:48 pm

Nonstop6h 21m

$267

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 3/13

7:15 pm-6:10 am

1 stop7h 55m

Boston Logan Intl

Thu 3/19

6:45 pm-11:59 pm

1 stop8h 14m

$268

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 3/26

7:17 pm-6:10 am

1 stop7h 53m

Boston Logan Intl

Wed 4/1

6:15 am-12:33 pm

1 stop9h 18m

$268

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 3/3

6:45 am-10:05 pm

2 stops12h 20m

Boston Logan Intl

Tue 3/10

3:15 pm-11:10 pm

2 stops10h 55m

$270

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 3/12

7:15 am-3:36 pm

Nonstop5h 21m

Boston Logan Intl

Thu 3/19

6:00 am-9:23 am

Nonstop6h 23m

$287

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 2/20

7:00 am-8:25 am

1 stop22h 25m

Boston Logan Intl

Fri 2/27

6:57 pm-12:15 am

1 stop8h 18m

$291

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 4/21

7:25 pm-8:15 am

2 stops9h 50m

Boston Logan Intl

Sat 4/25

1:50 pm-10:00 pm

2 stops11h 10m

$314

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 3/2

7:15 am-3:36 pm

Nonstop5h 21m

Boston Logan Intl

Tue 3/10

5:44 pm-9:50 am

1 stop19h 06m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 57 results
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Best time to book a flight from Portland to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Portland to Massachusetts?

Currently, April is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $104). Flying from Portland to Massachusetts in March is currently the most expensive (average of $216). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PDX to MA?

Find hourly flight availability from Portland to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2026.

It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 47% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated January 21, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Portland to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,775 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,089 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,829 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,191 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
JetBlue
7.2
Good
2,890 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Crew

8.5

Food

7.1

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Related info for your journey

Find useful and relevant information for your journey from Portland to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Massachusetts?

    Most people fly from Portland (PDX) if they book a flight from Portland to Massachusetts. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • How popular is this Portland to Massachusetts flight route?

    Flights from Portland to Massachusetts have been viewed 3 times in the past calendar month.

  • How long is the flight from Portland to Massachusetts?

    Airlines like Delta, Alaska Airlines, and United Airlines fly from Portland to Massachusetts in about 5h 23m. The time it takes to get you to your destination can typically vary by up to 2h 52m. Portland and Massachusetts are separated by a distance of 2528 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Portland to Massachusetts one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $79. Delta flights start at $98 while deals on JetBlue start at $98 one-way.

  • What are the most popular routes from Portland to Massachusetts?

    While some choose either Portland - Hartford Bradley Intl or Portland - Albany Intl, Portland - Boston Logan Intl is the most popular route from Portland to Massachusetts.

  • What are the most reliable airlines from Portland to Massachusetts?

    No one likes to see their flight delayed. When booking a flight from Portland to Massachusetts consider choosing Qatar Airways (77%), Alaska Airlines (77%) or Hawaiian Airlines (77%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Portland to Massachusetts?

    On average you can expect to pay $368 for a flight from Portland to Massachusetts. The cheapest flight overall is $118 while the most popular route, (Portland - Boston Logan Intl) is currently priced at $199.

  • Can I find deals for flights from Portland to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Portland to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Massachusetts.

  • Can I find deals for business class flights from Portland to Massachusetts?

    Yes. Cheapflights offers flight deals from Portland to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland to Massachusetts?

    Currently, April is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $104). Flying from Portland to Massachusetts in March is currently the most expensive (average of $216). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Portland to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Portland to Massachusetts

Discover the top 7 airlines that operate flights from Portland to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$291FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$108Average$312FlexibilityNo cancel feeOn-time85%
JetBlueCheapest$108Average$288FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$162Average$278FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$401FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$397FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$253Average$478FlexibilityNo cancel feeOn-time75%

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