PDX - MKE

$150 Find Cheap Flights from Portland to Milwaukee

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Milwaukee departing on 2/18. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Milwaukee

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Milwaukee, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Milwaukee, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$266
Overall average: $338
Delta
Tue 1/6Tue 1/13
PDX - MKE • 2 stops
Cheapest one-way
$150
Typical prices: $325-$370
Alaska Airlines
Wed 2/18
PDX - MKE • 1 stop
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 23% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Milwaukee (PDX-MKE)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Milwaukee 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 Portland to Milwaukee

Tue, Jan 6 - Tue, Jan 13
Delta Logo
7:37 pm - 8:53 am
PDX
-
MKE
11h 16m2 stops
Delta Logo
3:59 pm - 12:17 am
MKE
-
PDX
10h 18m2 stops
$266Delta
Tue, Jan 6 - Fri, Jan 9
Alaska Airlines Logo
5:10 am - 2:09 pm
PDX
-
MKE
6h 59m1 stop
Alaska Airlines Logo
3:53 pm - 9:23 am
MKE
-
PDX
19h 30m1 stop
$275Alaska Airlines
Wed, Jan 7 - Sat, Jan 10
Delta Logo
11:10 am - 9:15 pm
PDX
-
MKE
8h 05m2 stops
Delta Logo
6:40 am - 8:59 pm
MKE
-
PDX
16h 19m2 stops
$276Delta
Thu, Feb 12 - Mon, Feb 16
Alaska Airlines Logo
8:30 am - 2:51 pm
PDX
-
MKE
28h 21m1 stop
Alaska Airlines Logo
3:47 pm - 10:46 am
MKE
-
PDX
20h 59m1 stop
$285Alaska Airlines
Tue, Jan 6 - Mon, Jan 12
Alaska Airlines Logo
5:10 am - 2:09 pm
PDX
-
MKE
6h 59m1 stop
Alaska Airlines Logo
3:53 pm - 8:47 pm
MKE
-
PDX
6h 54m1 stop
$294Alaska Airlines
Fri, Feb 27 - Thu, Mar 5
Alaska Airlines Logo
6:00 am - 2:51 pm
PDX
-
MKE
6h 51m1 stop
Alaska Airlines Logo
3:47 pm - 10:46 am
MKE
-
PDX
20h 59m1 stop
$303Alaska Airlines
Mon, Jan 5 - Fri, Jan 9
Alaska Airlines Logo
5:10 am - 11:59 pm
PDX
-
MKE
16h 49m1 stop
Alaska Airlines Logo
3:53 pm - 9:23 am
MKE
-
PDX
19h 30m1 stop
$304Alaska Airlines
Thu, Jan 1 - Wed, Jan 14
United Airlines Logo
5:00 am - 3:00 pm
PDX
-
MKE
8h 00m1 stop
United Airlines Logo
4:05 pm - 9:12 pm
MKE
-
PDX
7h 07m1 stop
$306United Airlines
Tue, Jan 6 - Tue, Jan 13
Delta Logo
6:00 am - 3:19 pm
PDX
-
MKE
7h 19m1 stop
Delta Logo
3:59 pm - 12:17 am
MKE
-
PDX
10h 18m2 stops
$308Delta
Tue, Jan 6 - Tue, Jan 13
American Airlines Logo
6:00 am - 3:57 pm
PDX
-
MKE
7h 57m1 stop
American Airlines Logo
12:07 pm - 6:51 pm
MKE
-
PDX
8h 44m1 stop
$311American Airlines
Booking Insights

KAYAK's insights & trends for Portland to Milwaukee flights

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

What’s the cheapest day of the week to fly from Portland to Milwaukee?

The average price of all round-trip flights from Portland to Milwaukee clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Portland to Milwaukee, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Milwaukee, Wednesday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Milwaukee, 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 Portland to Milwaukee is January, where tickets cost $338 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $528 and $492 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Milwaukee, 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 Portland to Milwaukee, you should book around 4 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$150
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Portland to Milwaukee

When to book flights from Portland to Milwaukee

Are your dates flexible? Find out the best times to travel from Portland to Milwaukee based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Portland to Milwaukee

  • Which eco-friendly airline can I consider for my Portland to Milwaukee flight?

    United Airlines is one of the green airlines to consider for your travel from Portland to Milwaukee. The airline has made investments in sustainable practices and places a high priority on fuel efficiency and carbon emission reduction. Additionally, United Airlines is dedicated to eco-friendly ground operations, recycling, and waste minimization.

  • Which airline can I consider for my flight from Portland to Milwaukee with my kids?

    American Airlines is one of the family-friendly airlines to consider for the flight from Portland to Milwaukee. Under the “Kids Fly Free” program, American Airlines may offer discounts or free flights for children aged 2 to 14 in some flights, including Portland to Milwaukee flights. However, these minors have to be accompanied by an adult.

  • Which cities can I visit after deplaning from my Portland to Milwaukee flight at Milwaukee-Mitchell (MKE)?

    Besides being the major gateway to Milwaukee, MKE is also the destination airport for travelers connecting to nearby cities and towns. Among these cities are Madison, Racine, Chicago, and Green Bay. To connect to any of these cities, you can consider renting a car, taxi, or ride-share or Lyft services.

  • Can I rent a car after deplaning from my Portland to Milwaukee flight at Milwaukee-Mitchell (MKE)?

    Provided you have a valid driver's license, credit card, and reservation confirmation voucher, you can rent a car from any of the onsite car rentals. These car rentals include Avis, Budget, Enterprise, Hertz, and National. These car rentals are accessible from the car rental center located within a 10-minute ride from MKE terminals via a courtesy shuttle.

  • What is the cheapest flight from Portland to Milwaukee?

    In the last 3 days, the lowest price for a flight from Portland to Milwaukee was $150 for a one-way ticket and $266 for a round-trip.

  • Do I need a passport to fly between Portland and Milwaukee?

    No

  • Which airports will I be using when flying from Portland to Milwaukee?

    When flying out of Portland you will be using Portland. You will be landing at Milwaukee, also known as Milwaukee-Mitchell.

  • Which aircraft models fly most regularly from Portland to Milwaukee?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Portland to Milwaukee?

    Star Alliance, oneworld, and SkyTeam are the airline alliances operating flights between Portland and Milwaukee, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Portland to Milwaukee, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Portland to Milwaukee are Alaska Airlines and Delta. With an average price for the route of $422 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $441 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Portland to Milwaukee?

    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 Portland to Milwaukee.

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

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

    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 to Milwaukee with an airline and back to Portland with another airline. Booking your flights between Portland and MKE can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Milwaukee?

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

KAYAK’s top tips for finding a cheap flight from Portland to Milwaukee

  • You may need to factor in your layovers when planning or making a flight budget because most airlines provide indirect flights from Portland to Milwaukee. Some common layovers for this route are Salt Lake City (SLC), Atlanta Hartsfield-Jackson (ATL), and Las Vegas Harry Reid International Airport (LAS).
  • One of the benefits of considering Delta Air Lines when flying from Portland to Milwaukee is its ticket upgrade service. The airline allows travelers to upgrade their ticket from economy to First Class, especially during their layover, mostly through Atlanta Hartsfield-Jackson (ATL). You will typically have to wait for the airline's notification through email. The email informs you of the available discounted First-Class slots to be filled.
  • To connect from the city center to Portland (PDX) for your flight to Milwaukee, you will either board a taxi, a ride-share service such as Uber and Lyft, or the public means of transport, including buses and trains. The TriMet MAX Light Rail and the TriMet-operated Line 272 buses.
  • After deplaning from your Portland to Milwaukee flight at Milwaukee-Mitchell (MKE), you will use GreenLine (Route 55) bus, a taxi, or ride-shares like Uber and Lyft to connect to the city center. Among these options, buses offer a pocket-friendly and reliable option to the quicker taxis.
  • Portland (PDX) serves as the hub and the operating base for Alaska Airlines. The airline is therefore rated among the airlines with the highest number of flights from PDX. To book a flight that fits your schedule, you should consider using Alaska Airlines.

Reviews of the top 5 airlines serving from Portland to Milwaukee

 
See real verified KAYAK customer reviews for airlines flying from Portland to Milwaukee. 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 Portland to Milwaukee? 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
Alaska AirlinesOverall score based on 11469 reviews
7.8Comfort
7.1Food
8.5Crew
8.1Boarding
7.0Entertainment
Airline reviews

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

8.0 Excellentjanelle, Dec 2025
PDX - LAX
Read more Alaska Airlines reviews

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

The food selections were not good, and entertainment was non existent.

I would have liked if the flight existed. To be fair the federal government canceled it. But, since it WAS canceled, I would have liked it if Alaska Airlines had moved a finger to assist me rather then abandoning me with my luggage, unable to check it, for 14 hours in Portland. So federal regulations forbid them from storing my bag? Then at least help me find storage or SOMETHING.

It was all good, no delays which was a worry. All great

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

This was more with the third party booking through Kayak but my KTN for Pre-TSA, even though I entered it, wasn't assigned to my ticket when I got to the airport. I had to go through regular security. Also the Alaska app had trouble loading my ticket in the first place and I had to ask for it to be printed. Alaska Airlines was great but wanted you to know about this hiccup in the ticketing interface.

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

When I bought my tickets I up great my seats for extra $104 each seats 8A and 8B in the way back from Portland to Palm Springs they gave me the seats 15. I thought it was for round trip same seats . So I was very disappointed ☹️

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

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

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

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

Information on your arrival and departure airports