$140 Find Cheap Flights from Milwaukee to Oregon - Compare and Save

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Cheap Flights from Milwaukee to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Portland
Portland1 stop$279
Eugene
Eugene1 stop$362
Redmond
Redmond1 stop$459
Medford
Medford1 stop$479
Boise
Boise1 stop$319
Portland
Portland1 stop$279
Eugene
Eugene1 stop$362
Redmond
Redmond1 stop$459
Medford
Medford1 stop$479
Boise
Boise1 stop$319
Booking Insights

KAYAK's insights & trends for Milwaukee to Oregon flights

Get data-powered insights and trends into flights from Milwaukee 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 Milwaukee to Oregon?

Flight prices are below average for this route right now.

Flights to Oregon from Milwaukee usually cost between $454 and $646 in December.
The lowest price found in the past 5 days was $279 on Delta (Dec 5-Dec 12).

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

The cheapest month for flights from Milwaukee to Oregon is May, when tickets cost $385 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $565 and $523 respectively.

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

To get a below average price on the flight from Milwaukee 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 25 weeks before departure.

Good to know

Low season

January

Cheapest flight

$140
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Milwaukee to Portland

FAQs - booking Oregon flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee 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 Milwaukee 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 Milwaukee 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 Milwaukee 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 Milwaukee 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 5 airlines serving from Milwaukee to Oregon

 
Need help choosing which airline to fly with from Milwaukee 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.
7.9
Alaska AirlinesOverall score based on 13135 reviews
7.0Food
7.0Entertainment
7.8Comfort
8.1Boarding
8.5Crew
Airline reviews

Liked the flight was on time. Seats and leg room need major imptovement

8.0 ExcellentLori, Oct 2026
Read more Alaska Airlines reviews

Liked the flight was on time. Seats and leg room need major imptovement

Good. But these constant surveys are becoming wearing. Buy a clue.

It was good. Too long for older people. Service and support was great! Friendly crew!

Check in went smooth, flight was on time and our checked bag was delivered in a timely fashion.

Full, attentive service from the fist class cabin flight attendant was superb. Really exceeded expectations.

Direct and non stop. We were late checking in but had paid for our luggage to be checked and they easily took the bags at the gate for us. We unfortunately had to take our bags through TSA and lost a few items...

Oh the days of yore when there was some space. Wedged in by an extremely overweight passenger and sitting cramped for 4 hours is no one’s dream trip. One shouldn’t have to pay more for 1st class just to survive the trip. Literally the 1 day is ruined with recovery. Hugely obese need more room and should pay more for the required space. Staff were very nice, no hitches with baggage. I really dread flying., related to comfort.

My TSA precheck did not appear on my boarding pass, even though I entered my TTN at time of purchase and verified it was on the Alaska Airlines website under my reservation.

Very friendly staff, very responsive to complaints about the cabin temperature. 😁

First class only upgrades seat width. The bottom cushion of the seat sloped forward so much that I was constantly sliding out of my seat. The meal was awful, granola and dried fruit? Seriously, for what I paid to upgrade? I can bring my own sawdust and rotten fruit for a whole lot less. Priority boarding is great except when you have a hundred economy passengers stranding in the aisle slamming you in the face with their enormous carry ons and smelly asses right under your nose. I want my money back for that leg of my trip. It wasn’t worth the money for such a minimal upgrade.

Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

Flight time kept changing and so did the gate. It was very frustrating

It was as expected and I was grateful for the wheel chair help and ease of use.

Tight seats. Be prepared to sit in the middle if you are in boarding group C.

This was a connecting flight for me and I had already traveled for 7 hours. First, the Pilot didn’t show up and then the gate changed twice, after which the flight was rescheduled for 2 hours later. This made me late and I had to make other transportation arrangements to get home to Astoria another 1 hour & 45 minutes away. This cost me $250 more than it should have. Will not fly southwest again.

Long layover in Chicago. Wish that could have been lessened.

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

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!

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.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

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.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

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.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

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.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

All good except paid for wifi that did not work

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.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

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.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

We were told we had no flights before our flight was continually delayed then cancelled.

More options for your flight from Milwaukee to Oregon

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