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Massachusetts

$109+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
aug. 23 — aug. 301
lø. 8/23
lø. 8/30
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 august 18, 2025.

Round-trip from

$217
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$327

Good round-trip deal

$279 or less

Good one-way deal

$193 or less
From Portland to Massachusetts
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One-way flight from Portland to Massachusetts
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Highest demand for flights based on searches. 14% potential increase in price ($65 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 august 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/17. 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.
fr. 9/121:09 pmPDX - BOS
1 stop7h 44mAmerican Airlines
sø. 9/215:00 amBOS - PDX
1 stop7h 55mAmerican Airlines
Deal found 8/17$217
This American Airlines deal was found by Cheapflights users on 8/18. 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.
ma. 9/89:56 pmPDX - BOS
1 stop8h 31mAmerican Airlines
ti. 9/168:35 amBOS - PDX
1 stop8h 58mAmerican Airlines
Deal found 8/18$218
This American Airlines deal was found by Cheapflights users on 8/17. 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.
fr. 9/191:09 pmPDX - BOS
1 stop7h 44mAmerican Airlines
ti. 9/233:46 pmBOS - PDX
1 stop11h 19mAmerican Airlines
Deal found 8/17$222
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 10/17:15 amPDX - BOS
2 stops22h 28mFrontier
fr. 10/312:59 pmBOS - PDX
2 stops14h 13mFrontier
Deal found 8/18$236
This Delta deal was found by Cheapflights users on 8/18. 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.
to. 10/1610:23 amPDX - BOS
1 stop10h 21mDelta
fr. 10/177:20 amBOS - PDX
1 stop8h 29mDelta
Deal found 8/18$237
This Delta deal was found by Cheapflights users on 8/18. 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.
ma. 9/810:15 amPDX - BOS
1 stop10h 41mDelta
ti. 9/165:45 amBOS - PDX
1 stop7h 54mDelta
Deal found 8/18$238
This United Airlines deal was found by Cheapflights users on 8/17. 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.
on. 11/127:10 pmPDX - BOS
2 stops9h 24mUnited Airlines
ti. 11/184:20 pmBOS - PDX
1 stop8h 50mUnited Airlines
Deal found 8/17$242
This Southwest deal was found by Cheapflights users on 8/17. 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.
ti. 9/166:00 pmPDX - BOS
2 stops11h 10mSouthwest
ti. 9/235:40 pmBOS - PDX
1 stop8h 05mSouthwest
Deal found 8/17$252
This American Airlines deal was found by Cheapflights users on 8/17. 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.
to. 9/181:09 pmPDX - BOS
1 stop7h 44mAmerican Airlines
sø. 9/215:00 amBOS - PDX
1 stop7h 55mAmerican Airlines
Deal found 8/17$257
This Delta deal was found by Cheapflights users on 8/17. 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.
ti. 9/25:05 pmPDX - BOS
1 stop10h 20mDelta
fr. 10/36:45 pmBOS - PDX
1 stop8h 07mDelta
Deal found 8/17$262
This American Airlines deal was found by Cheapflights users on 8/17. 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.
to. 9/181:09 pmPDX - BOS
1 stop7h 44mAmerican Airlines
ti. 9/238:05 amBOS - PDX
1 stop11h 59mAmerican Airlines
Deal found 8/17$263
This Delta deal was found by Cheapflights users on 8/16. 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.
on. 9/1011:50 amPDX - BDL
1 stop8h 31mDelta
on. 9/245:35 amBDL - PDX
1 stop7h 44mDelta
Deal found 8/16$297

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 august 18, 2025.
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

on. 9/24

1:09 pm-11:53 pm

1 stop7h 44m

Boston Logan Intl

on. 10/1

5:36 pm-12:05 am

1 stop9h 29m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

on. 11/12

10:50 am-10:45 pm

1 stop8h 55m

Boston Logan Intl

ti. 11/18

1:35 pm-7:20 pm

1 stop8h 45m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

lø. 11/1

7:40 am-9:00 pm

1 stop10h 20m

Boston Logan Intl

on. 11/5

2:31 pm-9:23 pm

1 stop9h 52m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

lø. 11/8

10:20 am-8:50 pm

1 stop7h 30m

Boston Logan Intl

lø. 11/15

5:20 am-12:15 pm

1 stop9h 55m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

fr. 9/12

1:09 pm-11:53 pm

1 stop7h 44m

Boston Logan Intl

lø. 9/20

5:54 pm-12:05 am

1 stop9h 11m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

ma. 9/15

9:05 pm-8:10 am

1 stop8h 05m

Boston Logan Intl

ti. 9/23

5:40 pm-10:45 pm

1 stop8h 05m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

to. 10/30

11:58 pm-11:57 am

1 stop8h 59m

Boston Logan Intl

ti. 11/4

4:01 pm-11:26 pm

1 stop10h 25m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

fr. 9/12

1:09 pm-11:53 pm

1 stop7h 44m

Boston Logan Intl

sø. 9/21

5:00 am-9:55 am

1 stop7h 55m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

ti. 9/23

9:00 am-9:54 pm

1 stop9h 54m

Boston Logan Intl

ti. 9/30

3:46 pm-12:05 am

1 stop11h 19m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

ma. 10/27

5:00 am-3:00 pm

1 stop7h 00m

Boston Logan Intl

to. 10/30

6:35 am-5:20 pm

1 stop13h 45m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $218). Flying from Portland to Massachusetts in July is currently the most expensive (average of $311). 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 august 18, 2025.

When flying from Portland to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Portland to Massachusetts

Explore weekly flight availability from Portland to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated august 18, 2025.

The most flights from PDX to USMA are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

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 august 18, 2025.
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
10,000 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Hawaiian Airlines
7.8
Good
2,665 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
United Airlines
7.4
Good
8,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
JetBlue
7.2
Good
2,915 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.

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 4 times in the past calendar month.

  • How long is the flight from Portland to Massachusetts?

    Airlines like American Airlines, Southwest, and Delta fly from Portland to Massachusetts in about 7h 44m. The time it takes to get you to your destination can typically vary by up to 1h 11m. 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 Southwest, which is currently one of the cheapest options available, starting at $109. American Airlines flights start at $109 while deals on Frontier start at $137 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 (81%), Alaska Airlines (81%) or Hawaiian Airlines (81%) 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 $811 for a flight from Portland to Massachusetts. The cheapest flight overall is $108 while the most popular route, (Portland - Boston Logan Intl) is currently priced at $217.

  • 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, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $218). Flying from Portland to Massachusetts in July is currently the most expensive (average of $311). 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 9 airlines flying from Portland to Massachusetts

Discover the top 9 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 august 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$73Average$279FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$108Average$342FlexibilityNo cancel feeOn-time85%
DeltaCheapest$129Average$324FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$147Average$302FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$317FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$180Average$470FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$216Average$416FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$407FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$257Average$484FlexibilityNo cancel feeOn-time75%

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