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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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
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 October 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$254
(Southwest)

One-way from

$119
(Southwest)

Popular in

December

Cheapest in

February

Average price

$427

Good round-trip deal

$427 or less

Good one-way deal

$243 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. 13% potential increase in price ($60 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 October 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 October 10, 2025.

This Southwest deal was found by Cheapflights users on 10/9. 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 11/310:50 amPDX - BOS
1 stop8h 55mSouthwest
Fri 11/76:20 pmBOS - PDX
1 stop8h 55mSouthwest
Deal found 10/9$253
This Southwest deal was found by Cheapflights users on 10/9. 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.
Thu 11/276:30 amPDX - BOS
1 stop7h 25mSouthwest
Wed 12/312:20 pmBOS - PDX
2 stops12h 40mSouthwest
Deal found 10/9$254
This Southwest deal was found by Cheapflights users on 10/9. 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.
Wed 12/36:55 pmPDX - BOS
2 stops10h 20mSouthwest
Sun 12/76:20 pmBOS - PDX
1 stop8h 55mSouthwest
Deal found 10/9$258
This Delta deal was found by Cheapflights users on 10/7. 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 11/1312:35 amPDX - BOS
1 stop7h 22mDelta
Sun 11/167:15 amBOS - PDX
1 stop11h 18mDelta
Deal found 10/7$259
This Southwest deal was found by Cheapflights users on 10/9. 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.
Wed 11/1210:50 amPDX - BOS
1 stop8h 55mSouthwest
Sat 11/226:40 pmBOS - PDX
1 stop9h 00mSouthwest
Deal found 10/9$264
This Southwest deal was found by Cheapflights users on 10/9. 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.
Thu 12/46:55 pmPDX - BOS
2 stops10h 20mSouthwest
Fri 12/1212:05 pmBOS - PDX
1 stop9h 15mSouthwest
Deal found 10/9$268
This Southwest deal was found by Cheapflights users on 10/9. 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 12/98:00 amPDX - BOS
2 stops10h 35mSouthwest
Thu 12/186:55 pmBOS - PDX
1 stop8h 25mSouthwest
Deal found 10/9$269
This Delta deal was found by Cheapflights users on 10/7. 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.
Tue 12/212:32 amPDX - BOS
1 stop7h 28mDelta
Sat 12/136:55 pmBOS - PDX
1 stop16h 33mDelta
Deal found 10/7$271
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/267:10 pmPDX - BOS
1 stop7h 46mUnited Airlines
Thu 11/279:00 amBOS - PDX
1 stop11h 12mUnited Airlines
Deal found 10/9$272
This United Airlines deal was found by Cheapflights users on 10/9. 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 12/3111:45 pmPDX - BOS
1 stop9h 58mUnited Airlines
Wed 1/712:45 pmBOS - PDX
1 stop9h 11mUnited Airlines
Deal found 10/9$274
This Southwest deal was found by Cheapflights users on 10/9. 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 11/410:05 amPDX - BOS
2 stops9h 40mSouthwest
Tue 11/116:45 amBOS - PDX
1 stop15h 05mSouthwest
Deal found 10/9$275
This United Airlines deal was found by Cheapflights users on 10/9. 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 12/111:59 pmPDX - BOS
1 stop9h 44mUnited Airlines
Mon 12/86:00 amBOS - PDX
1 stop11h 47mUnited Airlines
Deal found 10/9$278

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 October 10, 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

Wed 1/14

6:45 am-10:05 pm

2 stops12h 20m

Boston Logan Intl

Mon 1/19

5:20 am-10:45 am

1 stop8h 25m

$254

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 11/19

5:05 pm-6:30 am

1 stop10h 25m

Boston Logan Intl

Sun 11/23

5:50 am-12:48 pm

1 stop9h 58m

$258

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 4/1

10:56 pm-10:39 am

1 stop8h 43m

Boston Logan Intl

Wed 4/22

12:30 pm-7:31 pm

1 stop10h 01m

$303

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 1/24

10:30 am-11:59 pm

1 stop10h 29m

Boston Logan Intl

Thu 1/29

5:20 pm-8:48 pm

Nonstop6h 28m

$312

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 12/13

12:32 am-11:00 am

1 stop7h 28m

Boston Logan Intl

Thu 12/25

5:45 am-11:05 am

1 stop8h 20m

$328

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 12/15

7:04 am-3:24 pm

Nonstop5h 20m

Boston Logan Intl

Thu 1/1

6:00 am-9:28 am

Nonstop6h 28m

$337

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 1/8

6:45 am-10:05 pm

2 stops12h 20m

Boston Logan Intl

Sat 1/10

12:55 pm-8:30 pm

2 stops10h 35m

$337

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 2/26

7:20 am-3:47 pm

Nonstop5h 27m

Boston Logan Intl

Sun 3/1

4:50 pm-8:15 pm

Nonstop6h 25m

$337

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 11/19

7:00 am-3:24 pm

Nonstop5h 24m

Boston Logan Intl

Sun 11/23

6:30 am-9:50 am

Nonstop6h 20m

$337

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 11/27

5:30 am-3:59 pm

1 stop7h 29m

Boston Logan Intl

Wed 12/31

5:30 am-10:49 am

1 stop8h 19m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

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 December is currently the most expensive (average of $255). 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 October 10, 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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 10, 2025.

The most flights from PDX to USMA are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 October 10, 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
11,049 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,049 reviews
Alaska Airlines
8.0
Very good
11,049 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
8.0
Very good
7,970 reviews
Alaska Airlines
8.0
Very good
11,049 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,775 reviews
Alaska Airlines
8.0
Very good
11,049 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,966 reviews
Alaska Airlines
8.0
Very good
11,049 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
JetBlue
7.2
Good
2,908 reviews
Alaska Airlines
8.0
Very good
11,049 reviews

Comfort

7.8

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 United Airlines fly from Portland to Massachusetts in about 8h 43m. The time it takes to get you to your destination can typically vary by up to 3h 37m. 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 Frontier start at $175 one-way.

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

    While some choose either Portland - Albany Intl or Portland - Hartford Bradley 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 (78%), Alaska Airlines (78%) 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 $419 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 December is currently the most expensive (average of $255). 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 October 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$122Average$360FlexibilityNo cancel feeOn-time85%
DeltaCheapest$129Average$315FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$302FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$310FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$222Average$414FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$398FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$256Average$484FlexibilityNo cancel feeOn-time75%

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