$176 Find Cheap Flights from Madison to Oregon - Compare and Save

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Cheap Flights from Madison to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Portland
Portland1 stop$326
Eugene
Eugene1 stop$359
Redmond
Redmond1 stop$359
Medford
Medford1 stop$359
Boise
Boise1 stop$339
Portland
Portland1 stop$326
Eugene
Eugene1 stop$359
Redmond
Redmond1 stop$359
Medford
Medford1 stop$359
Boise
Boise1 stop$339
Booking Insights

KAYAK's insights & trends for Madison to Oregon flights

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

How much is a round-trip flight from Madison to Oregon?

Flight prices are below average for this route right now.

Flights to Oregon from Madison usually cost between $348 and $499 in October.
The lowest price found in the past 5 days was $326 on United Airlines (Oct 27-Oct 31).

What is the cheapest Madison to Oregon flight route?

The cheapest ticket to Oregon from Madison found in the last 5 days was to Portland, at $424 round-trip. The most popular route is from Madison (MSN) to Eugene (EUG), and the cheapest round-trip airline ticket found on this route in the last 5 days was $469.

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

The cheapest time of day to fly to Oregon is generally in the morning, when round-trip flights cost $424 on average. The most expensive time of day to fly to Oregon is generally in the morning, which is peak travel time and where the average cost of a ticket is $424.

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

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $574 on average.

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

The cheapest month for flights from Madison to Oregon is January, when tickets cost $403 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $573 and $511 respectively.

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

To get a below average price on the flight from Madison to Oregon, you should book around 3 weeks before departure, which saves you about 1% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

February

Cheapest flight

$176
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Madison to Portland

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Madison 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 Madison to Oregon.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison 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 Madison 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 Madison 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 Madison 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 Madison to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Madison to Oregon

 
Need help choosing which airline to fly with from Madison 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.
7.8
DeltaOverall score based on 8499 reviews
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
7.8Comfort
Airline reviews

The Delta assistsed services were awesome for my aunt. So very helpful.

10.0 ExcellentBrian, Jun 2026
Read more Delta reviews

The Delta assistsed services were awesome for my aunt. So very helpful.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The Pilot was one of the best I've had, very informative about turbulence and got us to our destination early

Friendly boarding crew. Better could have been a bit more substantial food for this 3 plus hour flight.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Pilot Erika DeLong made us feel safe and at ease in a frankly scary time to be flying. Her warm smile and greeting and excellent command of the aircraft in foggy bumpy weather helped us all to calm our nerves and get us home safely.

Not enough room between rows and food was gross. $160 baggage charge?! Never again.

East Lounge in Denver was terrible. Turning away active military on orders? Really? Sad.

Clean and plenty of room for handbaggage. Leg room was cramped compared with the 777 from Frankfurt.

they made me check my carryon. There was space in the overhead bins.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

Cramped and uncomfortable seats. Not enough room for 6’2” person such as myself.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

Boarding was relatively fast and easy and the crew was attentive throughout.

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

Information on your arrival and departure airports