$108 Find Cheap Flights from Boston to Oregon

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Oregon departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Oregon.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Oregon.
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Cheap Flights from Boston to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$237
Eugene
Eugene2 stops$323
Redmond
Redmond1 stop$323
Medford
Medford1 stop$363
North Bend
North Bend1 stop$582
Boise
Boise1 stop$310
Portland
Portland1 stop$237
Eugene
Eugene2 stops$323
Redmond
Redmond1 stop$323
Medford
Medford1 stop$363
North Bend
North Bend1 stop$582
Boise
Boise1 stop$310

Book Cheap Boston to Oregon Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Oregon that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Oregon

Tue, Oct 21 - Sat, Oct 25
Delta Logo
5:45 am - 12:50 pmBOS-PDX
10h 05m1 stop
Delta Logo
2:10 pm - 1:13 amPDX-BOS
8h 03m1 stop
$237Delta
Find Deal
Sat, Nov 8 - Mon, Nov 17
Delta Logo
5:34 pm - 10:42 pmBOS-PDX
8h 08m1 stop
Delta Logo
12:35 am - 10:57 amPDX-BOS
7h 22m1 stop
$239Delta
Find Deal
Fri, Oct 17 - Sat, Oct 25
United Airlines Logo
4:15 pm - 10:45 pmBOS-PDX
9h 30m1 stop
United Airlines Logo
2:15 pm - 12:50 amPDX-BOS
7h 35m1 stop
$273United Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
United Airlines Logo
4:15 pm - 9:49 pmBOS-PDX
8h 34m1 stop
United Airlines Logo
11:59 pm - 1:13 pmPDX-BOS
10h 14m2 stops
$276United Airlines
Find Deal
Fri, Oct 31 - Sat, Nov 1
American Airlines Logo
2:18 pm - 8:17 pmBOS-PDX
8h 59m1 stop
American Airlines Logo
12:45 am - 11:35 amPDX-BOS
8h 50m1 stop
$292American Airlines
Find Deal
Thu, Nov 6 - Wed, Nov 12
Hawaiian Airlines Logo
7:00 am - 3:12 pmBOS-BOI
10h 12m1 stop
Hawaiian Airlines Logo
6:28 am - 12:20 amBOI-BOS
15h 52m1 stop
$310Hawaiian Airlines
Find Deal
Thu, Dec 11 - Sun, Jan 18
American Airlines Logo
5:33 am - 12:34 pmBOS-BOI
9h 01m1 stop
American Airlines Logo
7:32 am - 7:00 pmBOI-BOS
9h 28m1 stop
$312American Airlines
Find Deal
Fri, Oct 24 - Sat, Nov 8
Hawaiian Airlines Logo
6:15 am - 9:37 amBOS-PDX
6h 22mnonstop
Hawaiian Airlines Logo
1:38 pm - 12:20 amPDX-BOS
7h 42m1 stop
$320Hawaiian Airlines
Find Deal
Sun, Nov 23 - Fri, Nov 28
Alaska Airlines Logo
6:30 am - 9:50 amBOS-PDX
6h 20mnonstop
Alaska Airlines Logo
9:30 pm - 5:51 amPDX-BOS
5h 21mnonstop
$321Alaska Airlines
Find Deal
Thu, Nov 6 - Wed, Nov 12
Alaska Airlines Logo
7:00 am - 3:12 pmBOS-BOI
10h 12m1 stop
Alaska Airlines Logo
6:45 pm - 7:29 amBOI-BOS
10h 44m2 stops
$335Alaska Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Boston to Oregon flights

Get data-powered insights and trends into flights from Boston to Oregon to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Boston to Oregon flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Oregon from Boston found in the last 72 hours was to Portland, at $281 round-trip. The most popular route is from Boston (BOS) to Portland (PDX), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $281.

Can I save money by flying with a layover from Boston to Oregon?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $376, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Boston to Oregon?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Oregon, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Oregon is May, when tickets cost $289 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $511 and $429 respectively.

What’s the cheapest day of the week to fly from Boston to Oregon?

The average price of all round-trip flights from Boston to Oregon clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Oregon on a Thursday and more expensive on a Sunday. On your return trip to Boston, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

How far in advance should I book a flight from Boston to Oregon?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Oregon, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Oregon, you should book around 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$108
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Boston to Boise

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Boston to Oregon?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Oregon.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Oregon?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to Oregon is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Oregon?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Boston to Oregon with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Oregon?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Boston to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Oregon?

    The cheapest time of day to fly to Oregon is generally in the afternoon, when round-trip flights cost $371 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Oregon is generally at night, which is peak travel time and where the average cost of a ticket is $431.

Reviews of the top 5 airlines serving from Boston to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Boston to Oregon. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Oregon? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 10000 reviews
8.5Crew
8.1Boarding
7.0Entertainment
7.1Food
7.8Comfort
Airline reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

10.0 ExcellentAnonymous, Sep 2025ONT - PDX
Read more Alaska Airlines reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

It was a good experience! Thank you:) No sparkling mineral water… 🥲

Planes were on time. Pilot kept everyone updated. Crew was friendly and helpful

Flight was switched to a different airline. Caused scheduling issues. Flight delayed an hour, but arrived only 20 minutes late thanks to tail winds.

Upon arrival I was disappointed that the assist I requested to get to the baggage claim wasn't provided. The entire baggage area was not clearly marked and I wanted to store my baggage overnight, that wasn't available. I had to take it on the shuttle to the hotel!

The staff was extremely pleasant, and the ride was uneventful… If I were going to a place they serviced, I would take Alaska again

You no longer give receipts for baggage at the counter. And it is next to impossible to get it on your webpage. Spent 20 min trying and gave up... I need receipt to submit for reimbursement and don't have time to waste on your poor webpage Disappointing .....

The flight attendants were unkempt and show no customer service skills. They avoided eye contact. There were no smiles and they were dismissive and snarky.

Complete flight rebooked and 6 hours delayed. Zero accountability from the airline or Kayak for the issues and I’m injured which is why I opted to pay more to fly than drive because it’s painful to sit or stand too long. What was supposed to be a 3ish hour travel day turned into a 9 hour excruciatingly painful experience that has left me in worse pain than when I initially started.

I don’t like it stuff not friendly and no one help for my mom she 82 years old lady I requested wheel chair but no one provided and no one help.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

They we able to seat my companion and I next to each other. Plane’s temperature was very cool. Willl be more prepared on return trip.

All was good and they were able to seat my travel companion next to me. Thank you.

Like the ample leg room. May as well not bother with snacks if it's only a two ounce bag of pretzels. Didn't use the entertainment option. Was there one?

What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.

Kayak sold me a ticket after check in time. Could not check in. Could not get on flight.

Love you guys are so friendly and kind and wonderful

Agents talk too fast over intercom. I know it’s memorized and we’ve all heard it before. Just slow down a little. Stop charging for checked bags. I was pleased to get my bags promptly at each end of my flight.

Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.

It was clean and the crew was great. I wish the chairs could recline just a little more and you would provide small pillows for people with bad backs. My back is fused and a little support would be great.

I accidentally made this purchase and they wouldn’t refund me even though I called immediately to cancel it.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

Everything you need to know for your flight from Boston to Oregon

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