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$102+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Oregon to Massachusetts

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

Round-trip from

$233
(Delta)

One-way from

$102
(Delta)

Popular in

December

Cheapest in

February

Average price

$362

Good round-trip deal

$384 or less

Good one-way deal

$216 or less
From Oregon to Massachusetts
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One-way flight from Oregon to Massachusetts
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Highest demand for flights based on searches. 11% potential increase in price ($48 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 September 2025
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Price to beat on a round-trip flight from Oregon to Massachusetts.
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Price to beat on a one-way flight from Oregon to Massachusetts.
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Find 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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/13. 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 10/251:00 pmBOI - BOS
1 stop8h 48mDelta
Wed 10/295:45 amBOS - BOI
1 stop10h 17mDelta
Deal found 9/13$233
This Southwest deal was found by Cheapflights users on 9/12. 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 10/2212:40 pmPDX - BOS
1 stop7h 45mSouthwest
Tue 10/285:15 amBOS - PDX
1 stop7h 45mSouthwest
Deal found 9/12$235
This Delta deal was found by Cheapflights users on 9/12. 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.
Fri 11/1412:35 amPDX - BOS
1 stop7h 22mDelta
Wed 11/194:42 pmBOS - PDX
1 stop8h 23mDelta
Deal found 9/12$237
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Sat 10/117:35 pmPDX - ALB
2 stops12h 11mUnited Airlines
Sat 10/184:50 pmALB - PDX
1 stop8h 40mUnited Airlines
Deal found 9/12$238
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1011:59 pmPDX - ALB
2 stops9h 47mAmerican Airlines
Wed 11/192:05 pmALB - PDX
1 stop9h 13mAmerican Airlines
Deal found 9/13$239
This Southwest deal was found by Cheapflights users on 9/13. 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.
Fri 11/145:45 amPDX - BOS
1 stop9h 55mSouthwest
Wed 11/199:05 amBOS - PDX
2 stops12h 35mSouthwest
Deal found 9/13$242
This Delta deal was found by Cheapflights users on 9/13. 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 11/1011:15 pmPDX - ALB
2 stops10h 55mDelta
Wed 11/196:00 amALB - PDX
2 stops9h 48mDelta
Deal found 9/13$244
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Fri 10/2411:48 pmPDX - BDL
1 stop8h 49mAmerican Airlines
Tue 10/285:44 pmBDL - PDX
1 stop8h 22mAmerican Airlines
Deal found 9/12$249
This Southwest deal was found by Cheapflights users on 9/12. 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.
Mon 10/207:35 pmPDX - BOS
2 stops9h 50mSouthwest
Wed 10/295:05 pmBOS - PDX
1 stop8h 45mSouthwest
Deal found 9/12$253
This Southwest deal was found by Cheapflights users on 9/11. 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.
Mon 10/277:35 pmPDX - BOS
2 stops9h 50mSouthwest
Thu 10/305:15 amBOS - PDX
1 stop7h 55mSouthwest
Deal found 9/11$256
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 9/307:31 pmPDX - BOS
1 stop8h 04mDelta
Fri 10/311:13 amBOS - PDX
1 stop10h 38mDelta
Deal found 9/11$258
This Southwest deal was found by Cheapflights users on 9/13. 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 10/277:35 pmPDX - BOS
2 stops9h 50mSouthwest
Sat 11/16:30 amBOS - PDX
1 stop11h 10mSouthwest
Deal found 9/13$262

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 September 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

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Sat 10/25

1:00 pm-11:48 pm

1 stop8h 48m

Boston Logan Intl

Wed 10/29

5:45 am-2:02 pm

1 stop10h 17m

$233

BoiseBoston

BOI - BOS

BOIBOS

Boise Air Term. Gowen Fld

Tue 10/28

5:42 am-1:53 pm

1 stop6h 11m

Boston Logan Intl

Thu 10/30

6:15 am-3:05 pm

1 stop10h 50m

$233

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 10/27

10:10 pm-9:36 am

1 stop8h 26m

Boston Logan Intl

Sat 11/1

6:15 am-12:25 pm

1 stop9h 10m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Mon 10/20

7:59 pm-6:35 am

1 stop7h 36m

Boston Logan Intl

Wed 10/29

5:45 am-11:01 am

1 stop8h 16m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Sun 10/19

7:59 pm-6:35 am

1 stop7h 36m

Boston Logan Intl

Sat 10/25

5:34 am-10:29 am

1 stop7h 55m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 10/28

5:30 am-4:22 pm

1 stop7h 52m

Boston Logan Intl

Tue 11/4

6:15 am-12:20 pm

1 stop9h 05m

$237

PortlandBoston

PDX - BOS

PDXBOS

Portland

Tue 10/21

5:07 pm-5:35 am

1 stop9h 28m

Boston Logan Intl

Sat 10/25

6:15 am-12:25 pm

1 stop9h 10m

$237

PortlandAlbany

PDX - ALB

PDXALB

Portland

Sat 10/11

7:35 pm-10:46 am

2 stops12h 11m

Albany Intl

Sat 10/18

4:50 pm-10:30 pm

1 stop8h 40m

$238

PortlandBoston

PDX - BOS

PDXBOS

Portland

Fri 11/14

5:45 am-6:40 pm

1 stop9h 55m

Boston Logan Intl

Wed 11/19

9:05 am-6:40 pm

2 stops12h 35m

$242

EugeneBoston

EUG - BOS

EUGBOS

Eugene

Tue 2/24

1:25 pm-11:59 pm

1 stop7h 34m

Boston Logan Intl

Wed 2/25

5:55 pm-12:17 am

1 stop9h 22m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results
1
2
3
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6

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, January is the cheapest month in which you can book a flight from Oregon to Massachusetts (average of $218). Flying from Oregon to Massachusetts in July is currently the most expensive (average of $311). 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 September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Massachusetts as you normally would.

Weekly flight availability from Oregon to Massachusetts

Explore weekly flight availability from Oregon 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 September 15, 2025.

The most flights from USOR to USMA are scheduled on a Friday (7 on average). You will have fewer flight options on Monday, 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 September 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
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,956 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,931 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
JetBlue
7.2
Good
2,912 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 4 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 Delta, United Airlines, and Alaska Airlines fly from Oregon to Massachusetts in about 6h 11m. The time it takes to get you to your destination can typically vary by up to 8h 39m. Airlines will cover a distance of 2257 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 Delta ($102), American Airlines ($107), and Alaska Airlines ($168).

  • 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, January is the cheapest month in which you can book a flight from Oregon to Massachusetts (average of $218). Flying from Oregon to Massachusetts in July is currently the most expensive (average of $311). 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 Oregon to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Oregon to Massachusetts

Discover the top 9 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$115Average$458FlexibilityNo cancel feeOn-time85%
Spirit AirlinesCheapest$118Average$345FlexibilityNo cancel feeOn-time65%
DeltaCheapest$129Average$470FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$142Average$309FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$158Average$553FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$158Average$620FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$407FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$545FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$258Average$533FlexibilityNo cancel feeOn-time75%

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