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$119+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Southwest)

One-way from

$119
(United Airlines)

Popular in

December

Cheapest in

May

Average price

$461

Good round-trip deal

$377 or less

Good one-way deal

$208 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
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Highest demand for flights based on searches. 13% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 26, 2025.

This Delta deal was found by Cheapflights users on 11/24. 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 12/255:30 amPDX - BOS
1 stop7h 33mDelta
Thu 1/86:45 pmBOS - PDX
1 stop8h 32mDelta
Deal found 11/24$228
This Delta deal was found by Cheapflights users on 11/24. 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.
Fri 12/1212:32 amPDX - BOS
1 stop7h 28mDelta
Tue 12/166:10 amBOS - PDX
1 stop9h 30mDelta
Deal found 11/24$241
This Southwest deal was found by Cheapflights users on 11/24. 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.
Mon 12/810:50 amPDX - BOS
1 stop8h 55mSouthwest
Sat 12/135:20 amBOS - PDX
1 stop9h 55mSouthwest
Deal found 11/24$259
This United Airlines deal was found by Cheapflights users on 11/23. 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.
Mon 12/811:59 pmPDX - BOS
2 stops9h 34mUnited Airlines
Sat 12/136:00 amBOS - PDX
1 stop8h 48mUnited Airlines
Deal found 11/23$264
This Delta deal was found by Cheapflights users on 11/24. 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 12/2412:16 pmPDX - BOS
1 stop6h 46mDelta
Wed 1/74:25 pmBOS - PDX
1 stop9h 29mDelta
Deal found 11/24$268
This Southwest deal was found by Cheapflights users on 11/23. 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.
Fri 12/126:30 amPDX - BOS
1 stop8h 10mSouthwest
Tue 12/161:35 pmBOS - PDX
1 stop8h 45mSouthwest
Deal found 11/23$272
This Delta deal was found by Cheapflights users on 11/24. 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.
Sun 12/712:32 amPDX - BOS
1 stop7h 28mDelta
Thu 12/116:10 amBOS - PDX
1 stop9h 30mDelta
Deal found 11/24$285
This United Airlines deal was found by Cheapflights users on 11/25. 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.
Fri 12/1211:59 pmPDX - BOS
1 stop7h 51mUnited Airlines
Sun 12/146:00 amBOS - PDX
1 stop8h 48mUnited Airlines
Deal found 11/25$289
This American Airlines deal was found by Cheapflights users on 11/24. 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.
Thu 12/111:28 pmPDX - BOS
1 stop7h 45mAmerican Airlines
Mon 12/156:00 amBOS - PDX
1 stop9h 38mAmerican Airlines
Deal found 11/24$293
This United Airlines deal was found by Cheapflights users on 11/24. 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 12/108:30 amPDX - BOS
2 stops10h 03mUnited Airlines
Sun 12/146:00 amBOS - PDX
1 stop8h 48mUnited Airlines
Deal found 11/24$294
This Delta deal was found by Cheapflights users on 11/24. 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 12/255:30 amPDX - BOS
1 stop7h 33mDelta
Sun 1/47:55 pmBOS - PDX
1 stop15h 38mDelta
Deal found 11/24$296
This Alaska Airlines deal was found by Cheapflights users on 11/24. 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 12/249:42 pmPDX - BOS
Nonstop5h 28mAlaska Airlines
Wed 1/75:20 pmBOS - PDX
Nonstop6h 28mAlaska Airlines
Deal found 11/24$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 November 26, 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

Thu 1/8

6:20 am-4:50 pm

1 stop7h 30m

Boston Logan Intl

Sun 1/11

5:20 am-10:45 am

1 stop8h 25m

$208

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/5

9:45 pm-10:02 am

1 stop9h 17m

Boston Logan Intl

Wed 1/14

5:20 pm-12:17 am

1 stop9h 57m

$228

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/5

9:45 pm-10:02 am

1 stop9h 17m

Boston Logan Intl

Fri 1/9

5:35 pm-10:54 pm

1 stop8h 19m

$228

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/5

9:45 pm-10:02 am

1 stop9h 17m

Boston Logan Intl

Tue 1/13

5:50 am-12:46 pm

1 stop9h 56m

$228

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 1/6

7:37 pm-6:50 am

1 stop8h 13m

Boston Logan Intl

Thu 1/8

5:35 pm-10:54 pm

1 stop8h 19m

$228

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/5

9:45 pm-10:02 am

1 stop9h 17m

Boston Logan Intl

Thu 1/8

7:15 am-12:44 pm

1 stop8h 29m

$259

PortlandHartford

PDX - BDL

PDXBDL

Portland

Thu 2/12

11:46 am-10:19 pm

1 stop7h 33m

Hartford Bradley Intl

Sat 2/21

1:59 pm-9:22 pm

1 stop10h 23m

$327

PortlandHartford

PDX - BDL

PDXBDL

Portland

Tue 2/24

10:56 am-9:45 pm

1 stop7h 49m

Hartford Bradley Intl

Tue 3/3

7:35 am-1:44 pm

1 stop9h 09m

$327

PortlandHartford

PDX - BDL

PDXBDL

Portland

Tue 2/17

10:40 pm-10:37 am

1 stop8h 57m

Hartford Bradley Intl

Tue 2/24

8:45 am-6:09 pm

2 stops12h 24m

$360

PortlandHartford

PDX - BDL

PDXBDL

Portland

Sat 12/13

11:20 pm-8:48 am

1 stop6h 28m

Hartford Bradley Intl

Tue 12/16

2:12 pm-10:19 pm

1 stop11h 07m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 52 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 $228). 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 November 26, 2025.

It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 58% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Portland to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Portland to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Portland to Massachusetts?

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 November 26, 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
11,354 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
Alaska Airlines
8.0
Very good
11,354 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
Delta
7.9
Good
7,998 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
Hawaiian Airlines
7.8
Good
2,814 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
United Airlines
7.4
Good
9,046 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
JetBlue
7.2
Good
2,905 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

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 Southwest, Delta, and American Airlines fly from Portland to Massachusetts in about 7h 30m. The time it takes to get you to your destination can typically vary by up to 1h 47m. 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 United Airlines, which is currently one of the cheapest options available, starting at $119. Delta flights start at $120 while deals on American Airlines start at $169 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 Condor (100%), Qatar Airways (76%) or Alaska Airlines (76%) 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 $626 for a flight from Portland to Massachusetts. The cheapest flight overall is $168 while the most popular route, (Portland - Boston Logan Intl) is currently priced at $179.

  • 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 $228). 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$122Average$360FlexibilityNo cancel feeOn-time85%
DeltaCheapest$128Average$300FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$297FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$280FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$208Average$414FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$399FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$254Average$481FlexibilityNo cancel feeOn-time75%

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