$137 Find Cheap Flights from Milwaukee 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 Milwaukee to Oregon departing on 4/29. 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, 0 bags

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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$219
Eugene
Eugene1 stop$277
Redmond
Redmond1 stop$277
Medford
Medford1 stop$305
Boise
Boise1 stop$346
Portland
Portland1 stop$219
Eugene
Eugene1 stop$277
Redmond
Redmond1 stop$277
Medford
Medford1 stop$305
Boise
Boise1 stop$346

Book Cheap Milwaukee 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 Milwaukee 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 Milwaukee to Oregon

Fri, Apr 24 - Sun, Apr 26
Frontier Logo
6:29 pm - 11:42 am
MKE
-
PDX
19h 13m
1 stop
Frontier Logo
11:15 am - 4:10 pm
PDX
-
MKE
26h 55m
1 stop
$219Frontier
Tue, Apr 28 - Sat, May 2
Alaska Airlines Logo
7:00 am - 12:58 pm
MKE
-
RDM
7h 58m
1 stop
Alaska Airlines Logo
1:52 pm - 2:13 pm
RDM
-
MKE
22h 21m
1 stop
$277Alaska Airlines
Sat, Apr 25 - Sat, May 2
Southwest Logo
6:10 am - 12:00 pm
MKE
-
PDX
7h 50m
1 stop
Southwest Logo
9:35 am - 9:50 pm
PDX
-
MKE
10h 15m
2 stops
$282Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
4:05 pm - 11:00 pm
MKE
-
PDX
8h 55m
2 stops
Southwest Logo
5:30 am - 5:25 pm
PDX
-
MKE
9h 55m
2 stops
$287Southwest
Sat, Apr 11 - Wed, Apr 15
Delta Logo
4:48 pm - 9:53 pm
MKE
-
PDX
7h 05m
1 stop
Delta Logo
11:15 pm - 8:49 am
PDX
-
MKE
7h 34m
1 stop
$297Delta
Thu, Apr 23 - Sat, Apr 25
American Airlines Logo
6:40 pm - 11:57 pm
MKE
-
PDX
7h 17m
1 stop
American Airlines Logo
11:47 pm - 7:41 am
PDX
-
MKE
5h 54m
1 stop
$305American Airlines
Thu, Apr 2 - Sat, Apr 11
United Airlines Logo
7:41 pm - 11:59 pm
MKE
-
PDX
6h 18m
1 stop
United Airlines Logo
12:50 pm - 9:21 pm
PDX
-
MKE
6h 31m
1 stop
$306United Airlines
Sat, May 2 - Sat, May 16
Delta Logo
4:00 pm - 11:20 pm
MKE
-
MFR
9h 20m
2 stops
Delta Logo
5:15 am - 8:28 pm
MFR
-
MKE
13h 13m
2 stops
$307Delta
Sat, Apr 18 - Mon, Apr 27
United Airlines Logo
10:45 am - 5:45 pm
MKE
-
PDX
9h 00m
2 stops
United Airlines Logo
11:59 pm - 10:00 am
PDX
-
MKE
8h 01m
1 stop
$311United Airlines
Sat, May 9 - Wed, Aug 19
American Airlines Logo
7:01 am - 12:49 pm
MKE
-
BOI
6h 48m
1 stop
American Airlines Logo
1:14 pm - 7:57 pm
BOI
-
MKE
5h 43m
1 stop
$346American Airlines
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.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee 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 Milwaukee to Oregon is September, when tickets cost $358 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $506 and $497 respectively.

How far in advance should I book a flight from Milwaukee 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 Milwaukee 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 Milwaukee to Oregon, you should book around 5 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$137
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 12% 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

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee 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 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.
8.0
SouthwestOverall score based on 4320 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

My only complaint was how far it was from plane to baggage claim

I had a problem with my reservation and no one could help me understand what happened. I booked my flight months ago and received a confirmation email. In the confirmation email, it said that the flight would depart at 3:15 p.m. A few hours before the flight, I tried to go online and check in, and suddenly it said that the flight was leaving an hour earlier. I had to rush to get to the airport and almost didn't make it. No one could help me understand why this happened, and I'm really concerned that it might happen in the future. I would appreciate some support in this matter.

Cancelled the flight cuz they sent the WRONG plane and then they promised to rebook us and let us know within the hour what our next flight was. I have heard nothing after 12 hours and can’t get ahold of anyone.

nothing for delays and refuse service.when asked for the second flight. the first is good though

Not bad. Due to not buying a seat, on the way back, my seat was not assigned till 2 hrs before the flight left. Got me worried I wouldn’t have a seat.

It was not a good experience, the flight was delayed 3 hours, the gate staff were super pushy to get bags checked claiming it was a full flight, there were about a dozen open seats from what I could tell. The intercom from the pilot seemed to be broken, it sounded like the pilot was speaking with a mouth full of marbles.

There was an issue with the plane and it was late getting in. This caused me to miss my connecting flight from PDX to BOI. I had to ask if they would provide me with a food voucher and they did but didn’t seem to concerned about my delay.

The flight was delayed by 2 hours for “routine maintenance”and because of that I arrived much later iso my Uber ride home was $100 when it’s normally $50.

More or less, this seemed like a mismanaged group of great people who would crush at this job, if only they were given the resources to do so.

Plane destination at the Gates were mixed up at Spokane airport. Text from website didn't match rithet

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

Flights were constantly delayed. CRW took 50 minutes to get bags

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

Information on your arrival and departure airports