$109 Find Cheap Flights from Oregon to Maine

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Low seasonJanuary
High seasonJuly
Cheapest flight$109
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Portland to Boston

FAQs for booking flights from Oregon to Maine

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

    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 Oregon to Maine.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oregon to Maine 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 Oregon to Maine?

    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 Oregon to Maine 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 Oregon to Maine?

    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 Oregon to Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Maine?

    Based on KAYAK data, the cheapest day to fly to Maine is Saturday where round-trip tickets can be as cheap as $589. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $728 on average.

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

    The cheapest time of day to fly to Maine is generally in the evening, when round-trip flights cost $525 on average. Morning departures are around 30% more expensive than evening flights, on average. The most expensive time of day to fly to Maine is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $977.

  • What is the cheapest month to fly from Oregon to Maine?

    The cheapest month for flights from Oregon to Maine is February, when tickets cost $338 (return) on average. On the other hand, the most expensive months are May and June, when the average cost of round-trip tickets is $823 and $728 respectively.

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

    To get a below average price on the flight from Oregon to Maine, you should book around 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

  • How long is the flight to Maine?

    An average nonstop flight from Oregon to Maine takes 8h 55m, covering a distance of 2502 miles. The shortest route is Portland (PDX) to Boston (BOS) with an average flight time of 5h 20m.

  • What are the most popular destinations in Maine?

    Based on KAYAK flight searches, the most popular destination is Boston (88% of total searches to Maine). The next most popular destinations are Portland (8%) and Bangor (3%). Searches for flights to Augusta (0%) and to Rockland (0%) are also popular.

Reviews of the top 5 airlines serving from Oregon to Maine

 
Need help choosing which airline to fly with from Oregon to Maine? 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
SouthwestOverall score based on 4278 reviews
8.2Boarding
7.6Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

My flight was delayed a very short period of time but they did not hold my connecting flight to San Diego, also through United. So they closed the doors before we got off our plane. They would only have to help the door open for another five to ten minutes. So I missed a court deadline for a manditory mediation settlement conference for my client. I had to get an associate to be there in person and be on the phone with him relaying what he needs to do the entire time. The court was very upset with me and so was my client. United cannot be trusted.

Very rough getting into denver. my kid threw up it was so rough.

We were given vouchers we couldn’t use with a 5.5 hour delay

Cramped seat even in economy plus seat 10A. Over booked flight, no space for the bags

Why wasn't this flight departure scheduled eith another crew so that it could leave on time? When we arrived in Denver we had so little time between flights we had run to the connecting flight. We should received some credit for the inconvenience.

Really good 😊 the woman at the gate entrance was a little rude checking in our carry-on but i dont think she worked for the airline, she worked for the airport at sacramento, other than that amazing.

Gate agent did not hold flight for connection, provided no assistance to get new flight

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

This was a horrible experience. For a first class experience, my chair was held together by 3M tape - and I have a photo. The crew weren’t very attentive, somewhat dismissive and forgot my drink and snack, the chair reclined about 3 inches on a 6-hour cross country flight. I was also not informed that there was no lounge available in Newark airport because of renovations, so all around this was one of the worst experiences and I would actively avoid both American and Alaska Air going forward.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

They are still charging me after taking 466 and 833 for round trip from AR to to Bradley airport from 19 to 21. Then poor experience. Am hurt and I will say it on social media. Please stay away from this airline. I see in my bank account they are still taking 644. Am trying to stop it. I used to fly United airlines and I suggest that if you don't want extra charges and good service you go back there. American airlines delayed my flight again and I was late for my meeting, no recompensation but charging me over and over.

Pretty bad gate mgmt upon arrival. No open gates and we had to wait at midnight. Shouldn’t be a surprise that an aircraft is coming in.

The Wi-Fi was off, the arm rests are hard plastic.

The assistance with the wheel chairs was fabulous. All the people were so very friendly and helpful. I want to thank them all.

We almost missed our return flight. We got to the gate one minute from closing the cabin door, and the agent got us aboard the plane! We are so very grateful!!!!!

Flight was delayed in phoenix by 1 hour. When Kenny got to minneapolis st paul, Kenny missed his connecting flight to Duluth on Sun country air. Sun country customer service did nothing to help Kenny get home to Duluth. We will not fly with sun country ever again.

When we landed in Minneapolis from Providence, the ground crew was unable to move the jet bridge to meet our plane because the wheels were frozen. We waited patiently on the plane for about 45 minutes while they tried to solve this problem. It was mind boggling that this would not be more quickly resolved, or anticipated, in a place where sever winter weather is the norm. We stressed about meeting our connecting flight to Portland, which we assumed would be our only option for that day. Fortunately, when we finally raced from our gate to the next one, that Sun Country flight had been delayed so we didn't miss it. We decided not to take anything but direct flights from now on, no matter how much cheaper.

No line to check my bag. Reasonable overweight fee. When the connection was late due to weather, the gate agent opened the door and let me on the second flight. The plane waited for my luggage transfer. My bag arrived on time at my final destination:)

I had paid for a seat assignment at the time of reservation but when I checked in the night before it wasn’t there. Had to purchase another seat.

So unprofessional. They changed my connecting flight to a time that made it literally impossible to make the flight with no way to contact them or reject the changes. When I missed the flight as expected, there was no one to be found at their ticketing counter and the phone support put me on hold for an indefinite time. Since they didn't have another flight that day, all sun country air personell had left the airport (this was at 7pm) and my only options were to get a hotel for the night and come back the next afternoon to hopefully get rescheduled or buy a flight with another airline.

I purchased an aisle seat but was put in the middle seat surrounded by families with small sick children (3). That can happen anytime and I was prepared. The ticket agent questioned why I hadn’t paid for my luggage and had to explain that 2 pieces were included with my ticket. I hate that nickel and diming attitude. Please inform your staff better.

I know the airline has been open for 40 years and the flight crew looked just as old. The flight attendants were not friendly and rude. They should think of retiring this crew.

Book cheap flights from Oregon to Maine

Recent round-trip flight deals

8/11Mon
nonstopHawaiian Airlines
5h 23mPDX-BOS
8/19Tue
nonstopHawaiian Airlines
6h 17mBOS-PDX
$208
7/21Mon
nonstopHawaiian Airlines
5h 23mPDX-BOS
7/29Tue
nonstopHawaiian Airlines
6h 17mBOS-PDX
$209
8/19Tue
2 stopsSouthwest
11h 10mPDX-BOS
9/20Sat
1 stopSouthwest
7h 45mBOS-PDX
$222
8/8Fri
1 stopSouthwest
10h 50mPDX-BOS
8/12Tue
2 stopsSouthwest
10h 30mBOS-PDX
$228
8/16Sat
1 stopDelta
10h 40mPDX-BOS
9/19Fri
1 stopDelta
8h 07mBOS-PDX
$237
8/23Sat
1 stopDelta
8h 32mPDX-BOS
8/31Sun
1 stopDelta
9h 03mBOS-PDX
$258
9/29Mon
1 stopAmerican Airlines
7h 57mBOI-BOS
10/7Tue
2 stopsAmerican Airlines
11h 12mBOS-BOI
$319
9/9Tue
2 stopsAmerican Airlines
14h 13mRDM-PWM
9/13Sat
2 stopsAmerican Airlines
12h 59mPWM-RDM
$319
9/4Thu
1 stopUnited Airlines
10h 38mPDX-BGR
9/11Thu
1 stopUnited Airlines
9h 11mBGR-PDX
$339
9/4Thu
1 stopUnited Airlines
10h 38mPDX-BGR
9/11Thu
2 stopsUnited Airlines
11h 49mBGR-PDX
$344

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Recent one-way flight deals

8/4Mon
nonstopHawaiian Airlines
5h 23mPDX-BOS
$109
7/28Mon
1 stopAmerican Airlines
8h 07mPDX-BOS
$110
8/12Tue
2 stopsSouthwest
11h 10mPDX-BOS
$114
7/21Mon
1 stopDelta
6h 40mPDX-BOS
$119
7/26Sat
1 stopSouthwest
7h 30mPDX-BOS
$140
7/29Tue
1 stopDelta
10h 20mEUG-BOS
$145
8/31Sun
1 stopSun Country Air
8h 45mPDX-PWM
$163
8/12Tue
1 stopUnited Airlines
10h 15mPDX-PWM
$171
8/17Sun
1 stopSun Country Air
8h 46mPDX-PWM
$173
10/2Thu
1 stopUnited Airlines
10h 18mPDX-PWM
$195

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Last minute flights from Oregon to Maine

Last minute flight, train and bus deals

7/3Thu
multi-stopSun Country Air
7h 38mPDX-BOS
7/14Mon
multi-stopSun Country Air
19h 16mBOS-PDX
$435
7/2Wed
multi-stop
13h 02mPDX-BOS
7/9Wed
multi-stop
30h 18mBOS-PDX
$470
7/5Sat
multi-stopAmerican Airlines
11h 26mPDX-BOS
7/12Sat
multi-stopAmerican Airlines
9h 14mBOS-PDX
$482
7/5Sat
multi-stopSouthwest
10h 05mPDX-BOS
7/12Sat
multi-stopSouthwest
8h 05mBOS-PDX
$527
7/2Wed
multi-stopAmerican Airlines
8h 24mPDX-BOS
7/14Mon
multi-stopAmerican Airlines
11h 09mBOS-PDX
$552
7/4Fri
multi-stopDelta
7h 15mPDX-BOS
7/12Sat
multi-stopDelta
8h 19mBOS-PDX
$573
7/1Tue
multi-stopDelta
13h 51mRDM-BOS
7/15Tue
multi-stopDelta
10h 25mBOS-RDM
$599
7/4Fri
multi-stopUnited Airlines
7h 55mMFR-BOS
7/14Mon
multi-stopUnited Airlines
8h 40mBOS-MFR
$627
7/3Thu
multi-stopUnited Airlines
12h 53mPDX-BOS
7/14Mon
multi-stopUnited Airlines
9h 43mBOS-PDX
$657
7/1Tue
multi-stopSouthwest
10h 05mPDX-BOS
7/8Tue
multi-stopSouthwest
8h 30mBOS-PDX
$667

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Everything you need to know for your flight to Maine

Cabin class types available on flights to Oregon

Cabin classes available on flights to Oregon. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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