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$118+ Cheap flights from Oregon 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Oregon to Massachusetts

Cheapest flights from Oregon to Massachusetts
Explore the most affordable flight options available from Oregon to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This Delta deal was found by Cheapflights users on 12/13. 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.
Mon 12/295:30 amPDX - BOS
1 stop7h 38mDelta
Wed 1/75:20 pmBOS - PDX
1 stop9h 57mDelta
Deal found 12/13$241
This Delta deal was found by Cheapflights users on 12/13. 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 12/265:30 amPDX - BOS
1 stop7h 38mDelta
Thu 1/85:35 pmBOS - PDX
1 stop8h 19mDelta
Deal found 12/13$337
This Alaska Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/241:36 pmMFR - BOS
1 stop7h 47mAlaska Airlines
Tue 1/66:30 amBOS - MFR
1 stop9h 26mAlaska Airlines
Deal found 12/14$352
This Delta deal was found by Cheapflights users on 12/13. 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.
Sat 12/277:10 pmPDX - BOS
1 stop8h 32mDelta
Tue 1/66:10 amBOS - PDX
1 stop9h 22mDelta
Deal found 12/13$358
This Delta deal was found by Cheapflights users on 12/13. 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.
Mon 12/295:30 amPDX - BOS
1 stop7h 38mDelta
Tue 1/69:25 amBOS - PDX
2 stops17h 52mDelta
Deal found 12/13$364
This Alaska Airlines deal was found by Cheapflights users on 12/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:14 amPDX - BOS
Nonstop5h 31mAlaska Airlines
Tue 1/66:00 amBOS - PDX
Nonstop6h 28mAlaska Airlines
Deal found 12/13$377
This Delta deal was found by Cheapflights users on 12/13. 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.
Mon 12/295:30 amPDX - BOS
1 stop7h 38mDelta
Thu 1/89:25 amBOS - PDX
2 stops15h 50mDelta
Deal found 12/13$384
This Alaska Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/241:36 pmMFR - BOS
1 stop7h 47mAlaska Airlines
Fri 1/97:00 amBOS - MFR
1 stop8h 43mAlaska Airlines
Deal found 12/14$402
This Alaska Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/241:36 pmMFR - BOS
1 stop7h 47mAlaska Airlines
Wed 1/77:00 amBOS - MFR
2 stops12h 08mAlaska Airlines
Deal found 12/14$416
This Alaska Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/241:36 pmMFR - BOS
1 stop7h 47mAlaska Airlines
Thu 1/87:00 amBOS - MFR
2 stops12h 08mAlaska Airlines
Deal found 12/14$417
This Delta deal was found by Cheapflights users on 12/13. 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.
Mon 12/295:30 amPDX - BOS
1 stop7h 38mDelta
Mon 1/56:45 pmBOS - PDX
1 stop16h 48mDelta
Deal found 12/13$425
This Southwest deal was found by Cheapflights users on 12/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:10 amPDX - BOS
2 stops10h 15mSouthwest
Wed 1/74:50 pmBOS - PDX
1 stop8h 25mSouthwest
Deal found 12/13$432

Find flight deals from Oregon to Massachusetts

Keep the following information in mind while searching for Oregon to Massachusetts flight deals. Data was last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$203
(United Airlines)

One-way from

$118
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$556

Good round-trip deal

$417 or less

Good one-way deal

$193 or less
Provider with most accurate pricing for Portland-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Boston Logan Intl flights.
Search Deals
From Oregon to Massachusetts
Search Deals
One-way flight from Oregon to Massachusetts
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 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 Oregon to Massachusetts.
Search Deals
Price to beat on a one-way flight from Oregon to Massachusetts.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon 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 December 15, 2025.
Use the filters below to find and compare flights from Oregon to Massachusetts that are best for you.

Fly from

Oregon

Fly to

Massachusetts

Route

Depart

Return

Price

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 2/17

5:35 am-4:30 pm

1 stop7h 55m

Boston Logan Intl

Tue 2/24

1:20 pm-10:15 pm

2 stops11h 55m

$224

EugeneBoston

EUG - BOS

EUGBOS

Eugene

Mon 1/5

3:55 pm-6:10 am

1 stop11h 15m

Boston Logan Intl

Mon 1/12

4:20 pm-8:16 pm

1 stop30h 56m

$256

EugeneBoston

EUG - BOS

EUGBOS

Eugene

Wed 1/14

5:00 am-3:37 pm

1 stop7h 37m

Boston Logan Intl

Wed 1/21

7:25 am-1:07 pm

1 stop8h 42m

$257

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Fri 1/9

1:58 pm-11:30 pm

1 stop7h 32m

Boston Logan Intl

Mon 1/12

9:45 am-7:25 pm

1 stop11h 40m

$257

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Thu 1/15

3:01 pm-11:52 pm

1 stop6h 51m

Boston Logan Intl

Mon 1/19

12:45 pm-10:18 pm

1 stop11h 33m

$257

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Thu 1/15

5:30 am-2:05 pm

1 stop6h 35m

Boston Logan Intl

Tue 1/20

5:50 am-1:34 pm

1 stop9h 44m

$257

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Fri 1/16

2:37 pm-11:46 pm

1 stop7h 09m

Boston Logan Intl

Tue 1/20

3:15 pm-9:52 pm

1 stop8h 37m

$257

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Fri 1/16

3:01 pm-11:52 pm

1 stop6h 51m

Boston Logan Intl

Tue 1/20

5:50 am-1:34 pm

1 stop9h 44m

$257

EugeneBoston

EUG - BOS

EUGBOS

Eugene

Tue 1/13

6:36 am-10:22 pm

2 stops12h 46m

Boston Logan Intl

Sat 1/17

6:00 am-2:31 pm

1 stop11h 31m

$262

EugeneBoston

EUG - BOS

EUGBOS

Eugene

Wed 1/7

6:36 am-8:32 pm

1 stop10h 56m

Boston Logan Intl

Wed 1/14

9:51 am-9:01 pm

2 stops14h 10m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

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

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

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

Currently, April is the cheapest month in which you can book a flight from Oregon to Massachusetts (average of $103). Flying from Oregon to Massachusetts in March is currently the most expensive (average of $228). 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 OR to MA?

Find hourly flight availability from Oregon 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 December 15, 2025.

It’s typically best to fly out from Oregon to Massachusetts in the afternoon. Doing so could potentially save you 12% on the flight price compared to flying at noon, which is usually more expensive.

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

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

Travelers seeking maximum savings on their Oregon 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.

How much does it cost to fly round-trip from Oregon to Massachusetts?

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 December 15, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Oregon to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,452 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,008 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Hawaiian Airlines
7.8
Good
2,819 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,092 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
JetBlue
7.2
Good
2,895 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Oregon to Massachusetts flight route?

    The Oregon to Massachusetts flight path was viewed by 3 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Oregon to Massachusetts?

    Airlines like Southwest, Alaska Airlines, and United Airlines fly from Oregon to Massachusetts in about 7h 37m. The time it takes to get you to your destination can typically vary by up to 3h 38m. Airlines will cover a distance of 2584 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Oregon to Massachusetts are American Airlines ($83), Delta ($98), and JetBlue ($98).

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Oregon to Massachusetts (average of $103). Flying from Oregon to Massachusetts in March is currently the most expensive (average of $228). 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

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Alternative routes for Oregon to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Oregon to Massachusetts

Discover the top 8 airlines that operate flights from Oregon 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$122Average$427FlexibilityNo cancel feeOn-time85%
DeltaCheapest$124Average$436FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$128Average$295FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$158Average$453FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$158Average$478FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$425FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$521FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$255Average$527FlexibilityNo cancel feeOn-time75%

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