HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$109+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$197
(JetBlue)

One-way from

$109
(Hawaiian Airlines)

Popular in

December

Cheapest in

September

Average price

$408

Good round-trip deal

$226 or less

Good one-way deal

$153 or less
From Portland to Massachusetts
Search Deals
One-way flight from Portland to Massachusetts
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals
Price to beat on a round-trip flight from Portland to Massachusetts.
Search Deals
Price to beat on a one-way flight from Portland to Massachusetts.
Search Deals

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 June 12, 2025.

This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1511:40 pmPDX - BOS
Nonstop5h 20mJetBlue
Tue 7/226:55 pmBOS - PDX
Nonstop6h 20mJetBlue
Deal found 6/10$197
This Delta deal was found by Cheapflights users on 6/12. 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 9/101:46 pmPDX - BOS
1 stop7h 33mDelta
Sat 9/138:05 amBOS - PDX
1 stop11h 02mDelta
Deal found 6/12$217
This Southwest deal was found by Cheapflights users on 6/9. 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 7/35:30 amPDX - BOS
1 stop12h 40mSouthwest
Wed 7/95:20 pmBOS - PDX
1 stop9h 35mSouthwest
Deal found 6/9$222
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/255:30 pmPDX - BOS
1 stop11h 00mAlaska Airlines
Wed 7/306:32 pmBOS - PDX
1 stop8h 27mAlaska Airlines
Deal found 6/10$226
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Sun 8/1711:59 pmPDX - BOS
1 stop8h 00mUnited Airlines
Wed 8/205:05 pmBOS - PDX
1 stop8h 37mUnited Airlines
Deal found 6/10$237
This Hawaiian Airlines deal was found by Cheapflights users on 6/9. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/129:37 pmPDX - BOS
Nonstop5h 23mHawaiian Airlines
Tue 8/198:40 amBOS - PDX
1 stop11h 09mHawaiian Airlines
Deal found 6/9$267
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/25:29 pmPDX - BOS
1 stop9h 12mAmerican Airlines
Mon 8/185:29 amBOS - PDX
1 stop12h 00mAmerican Airlines
Deal found 6/10$269
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/811:07 pmPDX - MVY
1 stop10h 23mAmerican Airlines
Fri 7/111:00 pmMVY - PDX
2 stops12h 14mAmerican Airlines
Deal found 6/10$274
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/812:12 pmPDX - BOS
2 stops28h 22mSpirit Airlines
Sat 7/126:00 amBOS - PDX
2 stops30h 18mSpirit Airlines
Deal found 6/12$284
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1911:59 pmPDX - ACK
2 stops13h 37mAmerican Airlines
Tue 8/264:25 pmACK - PDX
1 stop8h 39mAmerican Airlines
Deal found 6/12$290
This Expedia deal was found by Cheapflights users on 6/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/89:37 pmPDX - BOS
Nonstop5h 23mMultiple Airlines
Sat 7/126:00 amBOS - PDX
2 stops30h 18mMultiple Airlines
Deal found 6/12$294
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/139:52 pmPDX - BDL
1 stop8h 08mAmerican Airlines
Wed 8/277:10 amBDL - PDX
1 stop10h 19mAmerican Airlines
Deal found 6/12$297

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 June 12, 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 7/15

11:40 pm-8:00 am

Nonstop5h 20m

Boston Logan Intl

Wed 7/23

6:55 pm-10:15 pm

Nonstop6h 20m

$197

PortlandBoston

PDX - BOS

PDXBOS

Portland

Wed 9/10

1:46 pm-12:19 am

1 stop7h 33m

Boston Logan Intl

Sat 9/13

8:05 am-4:07 pm

1 stop11h 02m

$217

PortlandBoston

PDX - BOS

PDXBOS

Portland

Thu 7/3

5:30 am-9:10 pm

1 stop12h 40m

Boston Logan Intl

Wed 7/9

5:20 pm-11:55 pm

1 stop9h 35m

$222

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 7/25

5:30 pm-7:30 am

1 stop11h 00m

Boston Logan Intl

Wed 7/30

6:32 pm-11:59 pm

1 stop8h 27m

$226

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sun 8/17

11:59 pm-10:59 am

1 stop8h 00m

Boston Logan Intl

Wed 8/20

5:05 pm-10:42 pm

1 stop8h 37m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 8/12

9:37 pm-6:00 am

Nonstop5h 23m

Boston Logan Intl

Tue 8/19

8:40 am-4:49 pm

1 stop11h 09m

$267

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sat 8/2

5:29 pm-5:41 am

1 stop9h 12m

Boston Logan Intl

Mon 8/18

5:29 am-2:29 pm

1 stop12h 00m

$269

PortlandWest Tisbury

PDX - MVY

PDXMVY

Portland

Tue 7/8

11:07 pm-12:30 pm

1 stop10h 23m

West Tisbury Martha's Vineyard

Fri 7/11

1:00 pm-10:14 pm

2 stops12h 14m

$274

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 7/8

12:12 pm-7:34 pm

2 stops28h 22m

Boston Logan Intl

Sat 7/12

6:00 am-9:18 am

2 stops30h 18m

$284

PortlandNantucket

PDX - ACK

PDXACK

Portland

Tue 8/19

11:59 pm-4:36 pm

2 stops13h 37m

Nantucket Memorial

Tue 8/26

4:25 pm-10:04 pm

1 stop8h 39m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 60 results
1
2
3
...
6

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, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $218). Flying from Portland to Massachusetts in June is currently the most expensive (average of $306). 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 June 12, 2025.

When flying from Portland to Massachusetts, 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 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 June 12, 2025.

The most flights from PDX to USMA are scheduled on a Thursday (11 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Portland to Massachusetts by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    To fly one-way, consider booking your trip with Hawaiian Airlines, which is currently one of the cheapest options available, starting at $109. Spirit Airlines flights start at $111 while deals on Southwest start at $114 one-way.

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

    While some choose either Portland - Albany Intl or Portland - Hartford Bradley 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 JetBlue (56%), Hawaiian Airlines (52%) or Condor (50%) 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 $650 for a flight from Portland to Massachusetts. The cheapest flight overall is $108 while the most popular route, (Portland - Boston Logan Intl) is currently priced at $197.

  • 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, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $218). Flying from Portland to Massachusetts in June is currently the most expensive (average of $306). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Los Angeles flights
Portland to John F Kennedy Intl flights
Portland to Las Vegas flights
Portland to Newark flights
Portland to Denver flights
Portland to O'Hare Intl flights
Portland to Santa Ana flights
Portland to San Francisco flights
Portland to Honolulu flights
Portland to Dallas/Fort Worth flights
Portland to Burbank flights
Portland to Ontario flights
Portland to Sky Harbor Intl flights
Portland to LaGuardia flights
Portland to Kahului flights
Portland to San Diego flights
Portland to Boston flights
Portland to Orlando flights
Portland to Reagan-National flights
Portland to Detroit flights
Portland to Salt Lake City flights
Portland to Minneapolis flights
Portland to San Jose flights
Portland to Dulles Intl flights
Portland to Atlanta flights
Boise to Seattle flights
Portland to Kailua-Kona flights
Portland to Omaha flights
Portland to Nashville flights
Portland to Austin flights
Boise to Las Vegas flights
Portland to Hobby flights
Boise to Los Angeles flights
Portland to Sacramento flights
Portland to Midway flights
Portland to Baltimore flights
Portland to George Bush Intcntl flights
Boise to O'Hare Intl flights
Portland to Anchorage flights
Portland to Reno flights
Boise to Denver flights
Portland to Palm Springs flights
Portland to New Orleans flights
Portland to Kansas City flights
Boise to San Diego flights
Portland to Lihue flights
Portland to Oakland flights
Portland to Albuquerque flights
Boise to Dallas/Fort Worth flights
Portland to Philadelphia flights

Top 9 airlines flying from Portland to Massachusetts

Discover the top 9 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$79Average$223FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$118Average$345FlexibilityNo cancel feeOn-time85%
DeltaCheapest$134Average$332FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$157Average$312FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$216Average$426FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$222Average$450FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$435FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$256Average$484FlexibilityNo cancel feeOn-time75%
Sun Country AirCheapest$333Average$453FlexibilityNo cancel feeOn-time83%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.