$301 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$381
Eugene
Eugene1 stop$436
Redmond
Redmond1 stop$409
Medford
Medford1 stop$399
Boise
Boise1 stop$369
Portland
Portland1 stop$381
Eugene
Eugene1 stop$436
Redmond
Redmond1 stop$409
Medford
Medford1 stop$399
Boise
Boise1 stop$369
Booking Insights

Price, demand and travel trends for Madison to Oregon flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Madison to Oregon recently?

The cheapest fare from Madison to Oregon in the last week was $381 round-trip, to Portland (PDX).

How do fares into airports in Oregon compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Oregon from Madison are:

• Portland (PDX) (avg. price $454)
• Eugene (EUG) (avg. price $514)
• Bend/Redmond (RDM) (avg. price $597)

What's the cheapest month to fly from Madison to Oregon?

February is typically the cheapest month to fly from Madison to Oregon, with round-trip fares averaging $402. December and November are usually the most expensive, averaging $569 and $550, respectively.

How do fares from Madison to Oregon vary by day of the week?

On average, Saturday is the cheapest day to fly from Madison to Oregon and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 48% more expensive to fly on a Sunday compared to Saturday.

What's the best time of day to fly from Madison to Oregon?

It's cheapest to fly to Oregon in the evening with average prices of $414. The morning is the most expensive time to fly, with average prices of $517.

What's the best time to book a flight from Madison to Oregon?

Book your flights 22 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 39% compared to booking at the last minute (within 2 weeks of departure).

Key details for Madison to Oregon flights

Low season

February

Cheapest flight

$301
Beat the crowds with an average 41% drop in travelers.
The most popular month to fly with an average 57% increase in travelers.
One-way flight from Madison to Portland

Your Madison to Oregon flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Madison to Oregon?

    Yes. Fares from Madison to Oregon are low right now. As a rule of thumb, a round-trip under $382 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Madison to Oregon?

    Over the past 12 months, round-trip fares from Madison to Oregon have typically cost between $382 and $613.

  • What are the main airports serving Oregon?

    There are 10 airports in Oregon. 68% of KAYAK users choose Portland (PDX) as their arrival airport, while 15% choose Eugene (EUG).

  • Which airlines fly nonstop from Madison to Oregon?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Madison to Oregon. One-stop options include:

    • United Airlines
    • Delta
    • American Airlines

  • Which destinations in Oregon can I fly nonstop from Madison?

    Based on the flight schedule for the next 3 months, there are no nonstop flights from Madison to Oregon. The most popular destination you can reach with one stop is Portland.

  • Which cabin classes are available from Madison to Oregon?

    On flights from Madison to Oregon you can book Economy Class or First Class.

  • What are some popular landmarks around Oregon?

    Oregon is home to many popular sights. KAYAK travelers' favorites include:

    • Moda Center
    • Oregon Convention Center
    • Tom McCall Waterfront Park
    • Keller Auditorium

Your guide to booking Madison to Oregon flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 22 weeks before your trip. KAYAK data shows fares in this window are around 39% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in February to save some money. It's typically the cheapest month on this route, while flights in December will cost you the most.
  • Fly out on a Saturday to get the cheapest fares. Avoid Sunday flights, which are about 48% more expensive.
  • If you're watching your budget, fly into Portland (PDX) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Portland, the most popular destination in Oregon. From there, it's easy to continue on to other popular spots such as Seaside, Cannon Beach and Lincoln City.

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 8719 reviews
7.8Comfort
8.5Crew
7.8Entertainment
8.1Boarding
7.2Food
Airline reviews

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

8.0 ExcellentCARMEN, Aug 2026
Read more Delta reviews

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

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.

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.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

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.

We were delayed a long time. We waited for “catering”. We didn’t get any food or accommodation for our wait. It made us land well after dinner time at our destination.

It was my first time flying with Alaska Airlines and it was a pleasure!

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.

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.

More options for your flight from Madison to Oregon

Complete your trip to Oregon with a hotel stay or car rental