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Massachusetts

$99+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Feb 15 — Feb 221
Sun 2/15
Sun 2/22
1 adult, Economy
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Cheap 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 16, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(American Airlines)

One-way from

$99
(Delta)

Popular in

December

Cheapest in

May

Average price

$337

Good round-trip deal

$347 or less

Good one-way deal

$238 or less
Provider with most accurate pricing for Portland-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Portland-Boston Logan Intl flights.
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From Portland to Massachusetts
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One-way flight from Portland to Massachusetts
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Portland to Massachusetts.
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Price to beat on a one-way flight from Portland to Massachusetts.
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Find 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 16, 2026.

This American Airlines deal was found by Cheapflights users on 1/14. 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 4/111:46 am
PDX
-
BOS
1 stop9h 19m
American Airlines
Wed 4/224:47 pm
BOS
-
PDX
1 stop9h 54m
American Airlines
Deal found 1/14$208
This Alaska Airlines deal was found by Cheapflights users on 1/15. 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
Tue 4/146:00 am
BOS
-
PDX
Nonstop6h 23m
Alaska Airlines
Deal found 1/15$217
This Delta deal was found by Cheapflights users on 1/14. 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 9/171:38 pm
PDX
-
BOS
1 stop7h 45m
Delta
Fri 9/253:30 pm
BOS
-
PDX
1 stop8h 19m
Delta
Deal found 1/14$218
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Tue 2/37:38 am
PDX
-
BOS
1 stop9h 21m
American Airlines
Sat 2/712:30 pm
BOS
-
PDX
1 stop10h 57m
American Airlines
Deal found 1/14$219
This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:25 pm
PDX
-
BOS
2 stops9h 50m
Southwest
Sat 4/253:30 pm
BOS
-
PDX
1 stop7h 55m
Southwest
Deal found 1/14$224
This Alaska Airlines deal was found by Cheapflights users on 1/15. 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 1/15$237
This American Airlines deal was found by Cheapflights users on 1/14. 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 4/81:14 pm
PDX
-
BOS
1 stop8h 08m
American Airlines
Mon 4/134:47 pm
BOS
-
PDX
1 stop9h 54m
American Airlines
Deal found 1/14$239
This Delta deal was found by Cheapflights users on 1/15. 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 1/296:15 am
PDX
-
BOS
1 stop9h 55m
Delta
Fri 2/612:45 pm
BOS
-
PDX
1 stop12h 35m
Delta
Deal found 1/15$242
This Delta deal was found by Cheapflights users on 1/14. 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 2/25:25 pm
PDX
-
BOS
1 stop9h 49m
Delta
Fri 2/66:45 pm
BOS
-
PDX
1 stop8h 32m
Delta
Deal found 1/14$243
This Delta deal was found by Cheapflights users on 1/14. 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.
Wed 4/15:19 am
PDX
-
BOS
1 stop7h 24m
Delta
Wed 4/811:15 am
BOS
-
PDX
1 stop10h 48m
Delta
Deal found 1/14$246
This Delta deal was found by Cheapflights users on 1/14. 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 4/21:56 pm
PDX
-
BOS
1 stop7h 03m
Delta
Sun 4/57:10 am
BOS
-
PDX
1 stop8h 59m
Delta
Deal found 1/14$248
This Delta deal was found by Cheapflights users on 1/15. 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.
Wed 2/116:50 am
PDX
-
BDL
1 stop7h 53m
Delta
Tue 2/176:05 am
BDL
-
PDX
1 stop9h 39m
Delta
Deal found 1/15$359

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 16, 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

Thu 4/2

1:56 pm-11:59 pm

1 stop7h 03m

Boston Logan Intl

Sat 4/4

5:15 pm-10:53 pm

1 stop8h 38m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 5/16

5:05 pm-6:09 am

1 stop10h 04m

Boston Logan Intl

Tue 5/19

6:35 pm-11:53 pm

1 stop8h 18m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 7/3

11:39 am-11:52 pm

1 stop9h 13m

Boston Logan Intl

Mon 7/6

6:35 pm-11:53 pm

1 stop8h 18m

$218

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 2/19

10:38 pm-9:15 am

1 stop7h 37m

Boston Logan Intl

Mon 2/23

1:55 pm-8:43 pm

1 stop9h 48m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 2/6

11:59 pm-1:20 pm

2 stops10h 21m

Boston Logan Intl

Sun 2/8

6:00 am-11:57 am

1 stop8h 57m

$242

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/28

12:40 am-10:51 am

1 stop7h 11m

Boston Logan Intl

Tue 2/3

3:30 pm-10:15 pm

1 stop9h 45m

$262

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 1/27

5:25 pm-6:14 am

1 stop9h 49m

Boston Logan Intl

Thu 2/5

6:45 pm-12:17 am

1 stop8h 32m

$262

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 7/15

1:38 pm-12:23 am

1 stop7h 45m

Boston Logan Intl

Wed 7/22

5:30 am-10:44 am

1 stop8h 14m

$269

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 7/8

7:14 pm-6:09 am

1 stop7h 55m

Boston Logan Intl

Tue 7/21

6:35 pm-11:53 pm

1 stop8h 18m

$269

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 4/8

7:00 am-3:27 pm

Nonstop5h 27m

Boston Logan Intl

Thu 4/16

6:00 am-9:23 am

Nonstop6h 23m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 60 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 $103). Flying from Portland to Massachusetts in March is currently the most expensive (average of $213). 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 16, 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 16, 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
11,727 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

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
11,727 reviews
Alaska Airlines
8.0
Very good
11,727 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

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
8,063 reviews
Alaska Airlines
8.0
Very good
11,727 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

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
2,828 reviews
Alaska Airlines
8.0
Very good
11,727 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

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
9,166 reviews
Alaska Airlines
8.0
Very good
11,727 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

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
2,889 reviews
Alaska Airlines
8.0
Very good
11,727 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

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, United Airlines, and American Airlines fly from Portland to Massachusetts in about 7h 03m. The time it takes to get you to your destination can typically vary by up to 34m. 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 $382 for a flight from Portland to Massachusetts. The cheapest flight overall is $128 while the most popular route, (Portland - Boston Logan Intl) is currently priced at $197.

  • 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 $103). Flying from Portland to Massachusetts in March is currently the most expensive (average of $213). 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.

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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 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$286FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$108Average$312FlexibilityNo cancel feeOn-time85%
JetBlueCheapest$108Average$288FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$278FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$401FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$397FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$256Average$477FlexibilityNo cancel feeOn-time75%

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