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$148+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PDX
jan 18 — jan 251
dom 1/18
dom 1/25
1 adult, Economy
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Cheap 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 dezembro 19, 2025.

This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 12/225:45 amBOS - PDX
1 stop8h 20mDelta
qua 1/76:00 amPDX - BOS
1 stop10h 10mDelta
Deal found 12/17$432
This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 12/1812:15 pmBOS - PDX
1 stop12h 09mAmerican Airlines
seg 1/2610:15 pmPDX - BOS
1 stop9h 14mAmerican Airlines
Deal found 12/17$439
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 12/2212:20 pmBOS - PDX
1 stop9h 28mUnited Airlines
qua 1/711:05 pmPDX - BOS
1 stop9h 07mUnited Airlines
Deal found 12/17$448
This Southwest deal was found by Cheapflights users on 12/17. 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.
seg 12/223:35 pmBOS - PDX
2 stops11h 55mSouthwest
qua 1/76:30 amPDX - BOS
1 stop7h 40mSouthwest
Deal found 12/17$457
This Delta deal was found by Cheapflights users on 12/18. 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.
ter 12/236:35 pmBOS - PDX
1 stop8h 20mDelta
sex 1/96:00 amPDX - BOS
1 stop10h 10mDelta
Deal found 12/18$458
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 12/2212:20 pmBOS - PDX
1 stop9h 28mUnited Airlines
dom 1/410:52 pmPDX - BOS
1 stop8h 45mUnited Airlines
Deal found 12/17$459
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 12/2212:20 pmBOS - PDX
1 stop9h 28mUnited Airlines
seg 1/511:55 pmPDX - BOS
2 stops10h 18mUnited Airlines
Deal found 12/17$464
This Southwest deal was found by Cheapflights users on 12/17. 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.
qui 12/181:45 pmBOS - PDX
2 stops10h 00mSouthwest
seg 1/266:20 amPDX - BOS
1 stop7h 30mSouthwest
Deal found 12/17$473
This Delta deal was found by Cheapflights users on 12/18. 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.
qua 12/316:05 amBOS - PDX
1 stop20h 16mDelta
seg 1/127:37 pmPDX - BOS
1 stop8h 13mDelta
Deal found 12/18$495
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 12/1811:49 amBOS - PDX
1 stop8h 37mMultiple Airlines
seg 1/267:00 amPDX - BOS
Nonstop5h 20mMultiple Airlines
Deal found 12/17$496
This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 12/2511:57 amBDL - PDX
2 stops14h 09mAmerican Airlines
qua 12/313:02 pmPDX - BDL
1 stop18h 04mAmerican Airlines
Deal found 12/17$572
This Delta deal was found by Cheapflights users on 12/18. 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.
qui 12/256:09 amBDL - PDX
1 stop7h 56mDelta
sex 1/27:15 amPDX - BDL
1 stop7h 45mDelta
Deal found 12/18$579

Find flight deals from Massachusetts to Portland

Keep the following information in mind while searching for Massachusetts to Portland flight deals. Data was last updated dezembro 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$148
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$557

Good round-trip deal

$379 or less

Good one-way deal

$206 or less
Provider with most accurate pricing for Boston Logan Intl-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Portland flights.
Search Deals
From Massachusetts to Portland
Search Deals
One-way flight from Massachusetts to Portland
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Portland.
Search Deals
Price to beat on a one-way flight from Massachusetts to Portland.
Search Deals

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 dezembro 19, 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

ter 1/13

1:20 pm-10:15 pm

2 stops11h 55m

Portland

ter 1/20

6:20 am-10:30 pm

1 stop13h 10m

$230

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

qua 1/21

6:00 am-1:45 pm

2 stops10h 45m

Portland

dom 1/25

11:59 pm-10:52 am

1 stop7h 53m

$242

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

qua 1/21

5:20 pm-8:48 pm

Nonstop6h 28m

Portland

dom 1/25

7:00 am-3:20 pm

Nonstop5h 20m

$257

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

sex 2/27

7:15 am-3:11 pm

1 stop10h 56m

Portland

dom 3/8

5:36 pm-6:49 am

1 stop10h 13m

$258

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

ter 1/27

5:20 pm-8:48 pm

Nonstop6h 28m

Portland

qui 1/29

1:38 pm-11:54 pm

1 stop7h 16m

$267

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

ter 1/13

5:20 pm-8:48 pm

Nonstop6h 28m

Portland

ter 1/20

7:00 am-3:20 pm

Nonstop5h 20m

$267

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

qui 1/22

9:30 am-6:10 pm

2 stops11h 40m

Portland

qui 1/22

11:59 pm-1:13 pm

2 stops10h 14m

$269

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

qua 3/25

5:45 am-12:33 pm

1 stop9h 48m

Portland

qua 4/1

8:37 am-7:58 pm

1 stop8h 21m

$276

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

dom 4/26

7:05 am-3:06 pm

1 stop11h 01m

Portland

ter 5/5

7:14 pm-6:09 am

1 stop7h 55m

$278

BostonPortland

BOS - PDX

BOSPDX

Boston Logan Intl

sex 1/16

4:16 pm-10:32 pm

1 stop9h 16m

Portland

sex 1/23

10:47 am-11:49 pm

2 stops10h 02m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 52 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 October is currently the most expensive (average of $208). 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 dezembro 19, 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 60% 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. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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, 11 users have taken a look at flights from Massachusetts to Portland.

  • How long is the flight from Massachusetts to Portland?

    For as low as $257, Southwest can have you in Portland from Massachusetts in 6h 28m. 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 $89 on American Airlines. Other airlines that offer cheap prices include JetBlue from $98 and Southwest from $99 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: Qatar Airways (83%), Hawaiian Airlines (83%), Alaska Airlines( 82%).

  • What are the cheapest flights from Massachusetts to Portland?

    Looking at all options, your cheapest flight can be booked for $158. While the most popular route (Boston Logan Intl - Portland) can be booked for $184 on average, our data indicates $882 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 October is currently the most expensive (average of $208). 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
Longview
Lake Oswego
Beaverton
McMinnville
Hillsboro
Troutdale
Cannon Beach
Long Beach
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham

Browse thousands of different options on Cheapflights for your next trip

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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 dezembro 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Sun Country AirCheapest$136Average$401FlexibilityNo cancel feeOn-time83%
Hawaiian AirlinesCheapest$138Average$346FlexibilityNo cancel feeOn-time85%
DeltaCheapest$144Average$305FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$172Average$329FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$178Average$307FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$391FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$393FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$243Average$460FlexibilityNo cancel feeOn-time75%

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