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$134+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PDX
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$235
(Southwest)

One-way from

$134
(Alaska Airlines)

Popular in

December

Cheapest in

May

Average price

$387

Good round-trip deal

$408 or less

Good one-way deal

$228 or less
Provider with most accurate pricing for Boston Logan Intl-Portland flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Portland flights.
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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. 10% potential increase in price ($43 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 October 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 October 14, 2025.

This Southwest deal was found by Cheapflights users on 10/11. 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.
Sat 11/226:40 pmBOS - PDX
1 stop9h 00mSouthwest
Wed 12/36:15 amPDX - BOS
1 stop7h 30mSouthwest
Deal found 10/11$235
This United Airlines deal was found by Cheapflights users on 10/11. 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 12/86:00 amBOS - PDX
1 stop8h 48mUnited Airlines
Tue 12/3011:45 pmPDX - BOS
1 stop9h 58mUnited Airlines
Deal found 10/11$237
This United Airlines deal was found by Cheapflights users on 10/11. 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 10/314:26 pmBOS - PDX
1 stop8h 44mUnited Airlines
Sat 11/811:59 pmPDX - BOS
1 stop7h 35mUnited Airlines
Deal found 10/11$238
This Delta deal was found by Cheapflights users on 10/13. 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 10/285:45 amBOS - PDX
1 stop10h 05mDelta
Thu 10/305:30 amPDX - BOS
1 stop7h 52mDelta
Deal found 10/13$239
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Thu 11/206:00 amBOS - PDX
1 stop8h 48mUnited Airlines
Tue 12/211:59 pmPDX - BOS
2 stops9h 34mUnited Airlines
Deal found 10/13$242
This Southwest deal was found by Cheapflights users on 10/11. 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 10/305:25 pmBOS - PDX
1 stop9h 40mSouthwest
Mon 11/38:00 amPDX - BOS
1 stop11h 45mSouthwest
Deal found 10/11$243
This United Airlines deal was found by Cheapflights users on 10/12. 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 10/286:00 amBOS - PDX
2 stops10h 47mUnited Airlines
Fri 10/3111:59 pmPDX - BOS
1 stop7h 35mUnited Airlines
Deal found 10/12$244
This United Airlines deal was found by Cheapflights users on 10/10. 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 11/186:00 amBOS - PDX
2 stops10h 47mUnited Airlines
Tue 11/1811:59 pmPDX - BOS
2 stops9h 29mUnited Airlines
Deal found 10/10$247
This Southwest deal was found by Cheapflights users on 10/11. 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 10/295:15 amBOS - PDX
2 stops10h 25mSouthwest
Mon 11/36:55 pmPDX - BOS
2 stops10h 20mSouthwest
Deal found 10/11$248
This Delta deal was found by Cheapflights users on 10/13. 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 11/146:52 pmBOS - PDX
1 stop8h 06mDelta
Sat 11/225:30 amPDX - BOS
1 stop22h 05mDelta
Deal found 10/13$249
This Delta deal was found by Cheapflights users on 10/12. 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 11/237:00 pmBOS - PDX
1 stop16h 31mDelta
Tue 12/212:32 amPDX - BOS
1 stop7h 28mDelta
Deal found 10/12$251
This Southwest deal was found by Cheapflights users on 10/12. 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 12/312:20 pmBOS - PDX
2 stops12h 40mSouthwest
Mon 12/86:15 amPDX - BOS
1 stop7h 30mSouthwest
Deal found 10/12$254

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 October 14, 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

Wed 10/29

7:25 am-1:47 pm

1 stop9h 22m

Portland

Fri 10/31

12:55 pm-11:39 pm

1 stop7h 44m

$239

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Wed 12/3

2:10 pm-10:00 pm

2 stops10h 50m

Portland

Mon 12/8

10:50 am-10:45 pm

1 stop8h 55m

$254

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Thu 10/30

7:20 am-2:38 pm

1 stop10h 18m

Portland

Sun 11/2

12:40 am-10:48 am

1 stop7h 08m

$258

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Wed 12/3

2:10 pm-10:00 pm

2 stops10h 50m

Portland

Wed 12/10

6:15 am-4:45 pm

1 stop7h 30m

$258

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Sat 2/21

4:50 pm-8:15 pm

Nonstop6h 25m

Portland

Sat 2/28

7:20 am-3:47 pm

Nonstop5h 27m

$267

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Thu 1/29

5:20 pm-8:48 pm

Nonstop6h 28m

Portland

Tue 2/3

7:05 am-3:25 pm

Nonstop5h 20m

$302

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Wed 11/12

3:15 pm-10:56 pm

1 stop10h 41m

Portland

Sun 11/16

7:10 pm-5:56 am

1 stop7h 46m

$303

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Thu 1/8

5:20 pm-8:48 pm

Nonstop6h 28m

Portland

Tue 1/13

9:10 am-11:59 pm

1 stop11h 49m

$312

AlbanyPortland

ALB - PDX

ALBPDX

Albany Intl

Fri 10/31

12:57 pm-8:17 pm

1 stop10h 20m

Portland

Thu 11/6

12:00 pm-10:48 pm

1 stop7h 48m

$315

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

Sat 10/25

5:34 am-10:29 am

1 stop7h 55m

Portland

Tue 11/4

12:40 am-10:48 am

1 stop7h 08m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

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, May is the cheapest month in which you can book a flight from Massachusetts to Portland (average of $113). Flying from Massachusetts to Portland in December is currently the most expensive (average of $263). 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 October 14, 2025.

One of the essential ways to save on airfare from Massachusetts to Portland is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 59% on airfare.

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

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

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

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 October 14, 2025.

The most flights from USMA to PDX are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, 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 $239, United Airlines can have you in Portland from Massachusetts in 9h 22m. Airlines will cover a distance of 2528 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 $143 on Frontier. Other airlines that offer cheap prices include Southwest from $144 and Delta from $160 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 Albany Intl - 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%), Condor (92%), Qatar Airways( 90%).

  • What are the cheapest flights from Massachusetts to Portland?

    Looking at all options, your cheapest flight can be booked for $168. While the most popular route (Boston Logan Intl - Portland) can be booked for $179 on average, our data indicates $748 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, May is the cheapest month in which you can book a flight from Massachusetts to Portland (average of $113). Flying from Massachusetts to Portland in December is currently the most expensive (average of $263). 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
Clackamas
Lincoln City
Lake Oswego
Beaverton
Hillsboro
McMinnville
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham
Troutdale

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Alternative routes for Massachusetts to Portland

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Top 8 airlines flying from Massachusetts to Portland

Discover the top 8 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Sun Country AirCheapest$136Average$401FlexibilityNo cancel feeOn-time83%
Hawaiian AirlinesCheapest$138Average$346FlexibilityNo cancel feeOn-time85%
DeltaCheapest$160Average$318FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$176Average$333FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$207Average$322FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$400FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$406FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$246Average$453FlexibilityNo cancel feeOn-time75%

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