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$109+ Cheap flights from Massachusetts to Portland (PDX)

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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PDX
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Massachusetts to Portland

Keep the following information in mind while searching for Massachusetts to Portland flight deals. Data was last updated August 20, 2025.

Round-trip from

$217
(Southwest)

One-way from

$109
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$367

Good round-trip deal

$262 or less

Good one-way deal

$158 or less
From Massachusetts to Portland
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One-way flight from Massachusetts to Portland
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Highest demand for flights based on searches. 11% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% 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 Massachusetts to Portland.
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Price to beat on a one-way flight from Massachusetts to Portland.
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Find flight deals from Massachusetts to Portland

Cheapest flights from Massachusetts to Portland
Explore the most affordable flight options available from Massachusetts to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/265:00 amBOS - PDX
1 stop8h 28mAmerican Airlines
Mon 9/296:07 amPDX - BOS
1 stop9h 27mAmerican Airlines
Deal found 8/19$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.
Sat 9/137:00 pmBOS - PDX
1 stop8h 05mAmerican Airlines
Fri 9/191:09 pmPDX - BOS
1 stop7h 44mAmerican Airlines
Deal found 8/18$218
This Southwest deal was found by Cheapflights users on 8/20. 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 12/31:35 pmBOS - PDX
1 stop8h 45mSouthwest
Sun 12/76:30 amPDX - BOS
1 stop13h 00mSouthwest
Deal found 8/20$222
This United Airlines deal was found by Cheapflights users on 8/19. 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 10/293:15 pmBOS - PDX
1 stop10h 41mUnited Airlines
Sun 11/27:10 pmPDX - BOS
1 stop7h 46mUnited Airlines
Deal found 8/19$232
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.
Fri 9/126:45 pmBOS - PDX
1 stop8h 07mDelta
Sat 9/205:10 pmPDX - BOS
1 stop10h 15mDelta
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.
Sat 9/137:05 amBOS - PDX
1 stop8h 30mDelta
Fri 9/197:05 pmPDX - BOS
1 stop8h 20mDelta
Deal found 8/18$238
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/21:40 pmBOS - PDX
1 stop10h 07mAmerican Airlines
Tue 9/911:18 amPDX - BOS
1 stop9h 35mAmerican Airlines
Deal found 8/19$252
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:50 pmBOS - PDX
1 stop8h 05mSouthwest
Thu 10/305:00 amPDX - BOS
1 stop7h 00mSouthwest
Deal found 8/18$257
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.
Tue 9/26:10 amBOS - PDX
1 stop9h 02mDelta
Mon 9/225:01 pmPDX - BOS
1 stop9h 34mDelta
Deal found 8/18$262
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:45 amBOS - PDX
1 stop9h 45mSouthwest
Sun 11/236:30 amPDX - BOS
1 stop13h 00mSouthwest
Deal found 8/18$263
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/96:10 amBOS - PDX
1 stop8h 39mUnited Airlines
Thu 9/1110:06 amPDX - BOS
1 stop7h 32mUnited Airlines
Deal found 8/19$267
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.
Wed 11/191:35 pmBOS - PDX
1 stop8h 45mSouthwest
Thu 11/2010:50 amPDX - BOS
1 stop8h 55mSouthwest
Deal found 8/17$268

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Portland 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 20, 2025.
Use the filters below to find and compare flights from Massachusetts to Portland that are best for you.

Fly from

Massachusetts

Fly to

Portland

Route

Depart

Return

Price

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Thu 11/6

6:20 pm-12:15 am

1 stop8h 55m

Portland

Wed 11/12

6:15 am-4:45 pm

1 stop7h 30m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Wed 9/24

5:36 pm-12:05 am

1 stop9h 29m

Portland

Sat 9/27

6:07 am-6:53 pm

1 stop9h 46m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Tue 11/4

1:35 pm-7:20 pm

1 stop8h 45m

Portland

Mon 11/10

5:45 am-6:40 pm

1 stop9h 55m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Fri 9/12

5:00 am-10:28 am

1 stop8h 28m

Portland

Tue 9/16

6:07 am-4:46 pm

1 stop7h 39m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Fri 11/7

6:20 pm-12:15 am

1 stop8h 55m

Portland

Mon 11/10

5:45 am-6:40 pm

1 stop9h 55m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Fri 9/26

5:00 am-10:28 am

1 stop8h 28m

Portland

Sun 10/5

11:58 pm-10:21 am

1 stop7h 23m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Wed 11/5

1:35 pm-7:20 pm

1 stop8h 45m

Portland

Mon 11/10

5:45 am-6:40 pm

1 stop9h 55m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Thu 10/30

2:18 pm-8:17 pm

1 stop8h 59m

Portland

Mon 11/3

10:15 pm-10:29 am

1 stop9h 14m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Wed 11/5

1:35 pm-7:20 pm

1 stop8h 45m

Portland

Tue 11/11

6:15 am-4:45 pm

1 stop7h 30m

$217

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Wed 10/29

2:47 pm-9:47 pm

1 stop10h 00m

Portland

Mon 11/3

10:15 pm-10:29 am

1 stop9h 14m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Massachusetts 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 Massachusetts to Portland

What is the cheapest month to book a flight from Massachusetts to Portland?

Currently, November is the cheapest month in which you can book a flight from Massachusetts to Portland (average of $277). Flying from Massachusetts to Portland in March is currently the most expensive (average of $368). 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 MA to PDX?

Find hourly flight availability from Massachusetts to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

When flying from Massachusetts to Portland, 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 Massachusetts to Portland

Explore weekly flight availability from Massachusetts to Portland. 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 20, 2025.

The most flights from USMA to PDX are scheduled on a Wednesday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Portland. 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 into for flights to Portland from Massachusetts?

    Most people fly into Portland (PDX) if they book a flight to Portland from Massachusetts. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • How popular is this Massachusetts to Portland flight route?

    Within the past month, 10 users have taken a look at flights from Massachusetts to Portland.

  • How long is the flight from Massachusetts to Portland?

    For as low as $297, Southwest can have you in Portland from Massachusetts in 7h 19m. Airlines will cover a distance of 2387 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Massachusetts to Portland one-way?

    One-way options have recently been found by users for as low as $109 on American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $131 and Frontier from $141 one-way.

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

    The most popular route from Massachusetts to Portland is Boston Logan Intl - Portland. You may also consider Hartford Bradley Intl - Portland or New Bedford Regional - Portland.

  • What are the most reliable airlines from Massachusetts to Portland?

    Before booking your flight to Portland from Massachusetts, check out the most reliable airlines to get you to your destination on time: Alaska Airlines (93%), Qatar Airways (90%), Condor( 90%).

  • What are the cheapest flights from Massachusetts to Portland?

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Boston Logan Intl - Portland) can be booked for $217 on average our data indicates $609 when flying from Massachusetts to Portland.

  • Can I find deals for flights from Massachusetts to Portland that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Portland.

  • Can I find deals for business class flights from Massachusetts to Portland?

    Yes. Cheapflights offers flight deals from Massachusetts to Portland 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 Massachusetts to Portland?

    Currently, November is the cheapest month in which you can book a flight from Massachusetts to Portland (average of $277). Flying from Massachusetts to Portland in March is currently the most expensive (average of $368). 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.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Beaverton
Clackamas
McMinnville
Lake Oswego
Hillsboro
Cannon Beach
Long Beach
Longview
Tigard
Depoe Bay
Stevenson
Wilsonville
Pacific City
Troutdale
Tillamook
Gresham
Lincoln City
Silverton

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Top 9 airlines flying from Massachusetts to Portland

Discover the top 9 airlines that operate flights from Massachusetts to Portland. 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$133Average$339FlexibilityNo cancel feeOn-time85%
DeltaCheapest$165Average$326FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$176Average$323FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$181Average$410FlexibilityNo cancel feeOn-time83%
Spirit AirlinesCheapest$200Average$256FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$216Average$357FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$420FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$410FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$246Average$444FlexibilityNo cancel feeOn-time75%

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