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$100+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(American Airlines)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$457

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. 13% potential increase in price ($58 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 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/11. 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 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
Fri 12/1211:44 amBOS - PDX
1 stop11h 33mAmerican Airlines
Deal found 11/11$208
This Delta deal was found by Cheapflights users on 11/12. 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.
Wed 12/312:32 amPDX - BOS
1 stop7h 28mDelta
Sun 12/75:45 amBOS - PDX
1 stop10h 09mDelta
Deal found 11/12$218
This Southwest deal was found by Cheapflights users on 11/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:55 amPDX - BOS
1 stop7h 10mSouthwest
Tue 12/161:35 pmBOS - PDX
1 stop8h 45mSouthwest
Deal found 11/10$219
This Southwest deal was found by Cheapflights users on 11/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:15 amPDX - BOS
1 stop7h 35mSouthwest
Tue 12/92:10 pmBOS - PDX
2 stops11h 25mSouthwest
Deal found 11/10$224
This Delta deal was found by Cheapflights users on 11/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:32 amPDX - BOS
1 stop7h 28mDelta
Thu 12/46:55 pmBOS - PDX
1 stop8h 21mDelta
Deal found 11/10$237
This Delta deal was found by Cheapflights users on 11/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2611:35 amPDX - BOS
1 stop9h 19mDelta
Wed 12/37:15 amBOS - PDX
1 stop11h 18mDelta
Deal found 11/11$239
This Delta deal was found by Cheapflights users on 11/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2611:35 amPDX - BOS
1 stop9h 19mDelta
Thu 12/410:15 amBOS - PDX
1 stop8h 53mDelta
Deal found 11/11$241
This United Airlines deal was found by Cheapflights users on 11/12. 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.
Fri 12/55:00 amPDX - BOS
1 stop7h 42mUnited Airlines
Sat 12/610:30 amBOS - PDX
2 stops11h 15mUnited Airlines
Deal found 11/12$242
This Delta deal was found by Cheapflights users on 11/12. 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.
Thu 12/186:15 amPDX - BOS
1 stop8h 03mDelta
Wed 1/75:20 pmBOS - PDX
1 stop9h 57mDelta
Deal found 11/12$248
This Southwest deal was found by Cheapflights users on 11/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:55 pmPDX - BOS
2 stops10h 20mSouthwest
Fri 12/1212:05 pmBOS - PDX
1 stop9h 15mSouthwest
Deal found 11/10$253
This United Airlines deal was found by Cheapflights users on 11/10. 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.
Wed 12/101:14 pmPDX - BDL
1 stop7h 16mUnited Airlines
Wed 12/176:10 amBDL - PDX
1 stop8h 38mUnited Airlines
Deal found 11/10$354
This Delta deal was found by Cheapflights users on 11/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:20 pmPDX - ALB
1 stop6h 37mDelta
Tue 12/94:58 pmALB - PDX
1 stop8h 12mDelta
Deal found 11/11$359

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 13, 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

Fri 12/12

5:45 am-6:40 pm

1 stop9h 55m

Boston Logan Intl

Sun 12/14

6:55 pm-12:20 am

1 stop8h 25m

$219

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/19

12:40 am-10:51 am

1 stop7h 11m

Boston Logan Intl

Sun 1/25

12:45 pm-10:24 pm

1 stop12h 39m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 12/11

6:15 am-4:45 pm

1 stop7h 30m

Boston Logan Intl

Wed 12/17

1:35 pm-7:20 pm

1 stop8h 45m

$277

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/7

7:00 am-3:20 pm

Nonstop5h 20m

Boston Logan Intl

Tue 1/13

5:20 pm-8:48 pm

Nonstop6h 28m

$297

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sun 12/7

11:59 pm-12:33 pm

2 stops9h 34m

Boston Logan Intl

Mon 12/15

6:00 am-11:48 am

1 stop8h 48m

$300

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 12/10

12:32 am-11:00 am

1 stop7h 28m

Boston Logan Intl

Wed 12/17

5:45 am-12:54 pm

1 stop10h 09m

$308

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 1/5

9:10 am-12:05 am

1 stop11h 55m

Boston Logan Intl

Tue 1/13

6:50 am-3:45 pm

2 stops11h 55m

$314

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 1/9

7:00 am-3:20 pm

Nonstop5h 20m

Boston Logan Intl

Tue 1/13

5:20 pm-8:48 pm

Nonstop6h 28m

$317

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 1/7

7:00 am-3:20 pm

Nonstop5h 20m

Boston Logan Intl

Sun 1/11

5:20 pm-8:48 pm

Nonstop6h 28m

$317

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 12/6

7:04 am-3:24 pm

Nonstop5h 20m

Boston Logan Intl

Sun 12/7

4:40 pm-8:10 pm

Nonstop6h 30m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 58 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 $227). 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 13, 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.

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 November 13, 2025.

The most flights from PDX to USMA are scheduled on a Monday (6 on average). You will have fewer flight options on Wednesday, 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 November 13, 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
11,281 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

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
11,281 reviews
Alaska Airlines
8.0
Very good
11,281 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

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
8,007 reviews
Alaska Airlines
8.0
Very good
11,281 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

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
2,809 reviews
Alaska Airlines
8.0
Very good
11,281 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

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
9,015 reviews
Alaska Airlines
8.0
Very good
11,281 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

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
11,281 reviews

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

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 Alaska Airlines fly from Portland to Massachusetts in about 5h 20m. The time it takes to get you to your destination can typically vary by up to 4h 35m. 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 Delta, which is currently one of the cheapest options available, starting at $119. United Airlines flights start at $124 while deals on American Airlines start at $184 one-way.

  • 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 $227). 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 13, 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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