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Massachusetts

$118+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$213
(Southwest)

One-way from

$118
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$466

Good round-trip deal

$427 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
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($56 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 6, 2025.

This Southwest deal was found by Cheapflights users on 11/4. 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 12/48:00 amPDX - BOS
1 stop11h 45mSouthwest
Mon 12/81:35 pmBOS - PDX
1 stop8h 45mSouthwest
Deal found 11/4$213
This Southwest deal was found by Cheapflights users on 11/5. 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 12/310:50 amPDX - BOS
1 stop8h 55mSouthwest
Tue 12/91:35 pmBOS - PDX
2 stops12h 00mSouthwest
Deal found 11/5$224
This Southwest deal was found by Cheapflights users on 11/5. 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 12/48:00 amPDX - BOS
1 stop11h 45mSouthwest
Tue 12/92:10 pmBOS - PDX
2 stops10h 50mSouthwest
Deal found 11/5$230
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/45:59 pmPDX - BOS
1 stop10h 15mAmerican Airlines
Mon 12/82:24 pmBOS - PDX
1 stop8h 53mAmerican Airlines
Deal found 11/5$235
This American Airlines deal was found by Cheapflights users on 11/4. 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 12/25:59 pmPDX - BOS
1 stop9h 19mAmerican Airlines
Sun 12/76:00 amBOS - PDX
1 stop9h 38mAmerican Airlines
Deal found 11/4$236
This Delta deal was found by Cheapflights users on 11/5. 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
Wed 12/34:46 pmBOS - PDX
1 stop8h 24mDelta
Deal found 11/5$237
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Tue 12/211:59 pmPDX - BOS
2 stops9h 34mUnited Airlines
Sun 12/76:00 amBOS - PDX
1 stop8h 48mUnited Airlines
Deal found 11/4$242
This Southwest deal was found by Cheapflights users on 11/5. 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 11/196:15 amPDX - BOS
1 stop7h 30mSouthwest
Mon 12/81:35 pmBOS - PDX
1 stop8h 45mSouthwest
Deal found 11/5$248
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/197:10 pmPDX - BOS
2 stops9h 24mUnited Airlines
Mon 12/84:20 pmBOS - PDX
1 stop8h 55mUnited Airlines
Deal found 11/5$253
This American Airlines deal was found by Cheapflights users on 11/4. 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 11/1811:43 amPDX - BOS
1 stop9h 00mAmerican Airlines
Thu 11/2012:05 pmBOS - PDX
1 stop12h 10mAmerican Airlines
Deal found 11/4$259
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:04 amPDX - BOS
Nonstop5h 20mAlaska Airlines
Wed 12/104:40 pmBOS - PDX
Nonstop6h 30mAlaska Airlines
Deal found 11/4$264
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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.
Sat 12/67:04 amPDX - BOS
Nonstop5h 20mAlaska Airlines
Tue 12/94:40 pmBOS - PDX
Nonstop6h 30mAlaska Airlines
Deal found 11/5$267

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 6, 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

Tue 1/13

1:53 pm-11:52 pm

1 stop6h 59m

Boston Logan Intl

Sat 1/17

7:15 am-12:44 pm

1 stop8h 29m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 3/13

6:59 pm-5:50 am

1 stop7h 51m

Boston Logan Intl

Mon 3/16

5:45 am-12:37 pm

1 stop9h 52m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/14

5:30 pm-6:14 am

1 stop9h 44m

Boston Logan Intl

Wed 1/21

4:20 pm-11:55 pm

1 stop10h 35m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 3/9

12:55 am-11:06 am

1 stop7h 11m

Boston Logan Intl

Wed 3/11

11:00 am-7:11 pm

1 stop11h 11m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 12/11

5:30 am-4:03 pm

1 stop7h 33m

Boston Logan Intl

Sun 12/14

8:05 am-12:54 pm

1 stop7h 49m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/14

7:37 pm-6:50 am

1 stop8h 13m

Boston Logan Intl

Fri 1/16

6:45 pm-12:17 am

1 stop8h 32m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 1/13

1:38 pm-11:54 pm

1 stop7h 16m

Boston Logan Intl

Wed 1/21

5:20 pm-8:48 pm

Nonstop6h 28m

$277

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/14

7:00 am-3:20 pm

Nonstop5h 20m

Boston Logan Intl

Sat 1/17

7:00 am-12:38 pm

1 stop8h 38m

$277

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 12/3

7:04 am-3:37 pm

1 stop29h 33m

Boston Logan Intl

Tue 12/9

4:40 pm-8:10 pm

Nonstop6h 30m

$288

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 12/25

11:45 pm-12:43 pm

1 stop9h 58m

Boston Logan Intl

Thu 1/1

6:01 am-11:58 am

1 stop8h 57m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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 $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 6, 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.

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 6, 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
11,243 reviews

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

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
11,243 reviews
Alaska Airlines
8.0
Very good
11,243 reviews

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

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
7.9
Good
8,001 reviews
Alaska Airlines
8.0
Very good
11,243 reviews

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

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
2,804 reviews
Alaska Airlines
8.0
Very good
11,243 reviews

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

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
9,004 reviews
Alaska Airlines
8.0
Very good
11,243 reviews

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

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
2,907 reviews
Alaska Airlines
8.0
Very good
11,243 reviews

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

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 Delta, United Airlines, and Southwest fly from Portland to Massachusetts in about 6h 59m. The time it takes to get you to your destination can typically vary by up to 6h 01m. 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 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 (83%), Qatar Airways (72%) or Alaska Airlines (72%) 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 $464 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 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$122Average$360FlexibilityNo cancel feeOn-time85%
DeltaCheapest$129Average$307FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$299FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$284FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$208Average$414FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$399FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$254Average$487FlexibilityNo cancel feeOn-time75%

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