PDX - MKE

$159 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 5/19. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$317
Typical prices: $606-$419
Delta
Wed 5/20Tue 5/26
PDX - MKE • 1 stop
Cheapest one-way
$159
Typical prices: $174-$325
American Airlines
Tue 5/19
PDX - MKE • 1 stop
Top airlines
Cheapest • from $317 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Portland and Milwaukee. You'll need at least 1 connection.
Insights
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Top layover airports
Cheapest • Avg $304 (round-trip)
Shortest trip • 6h 07m (one-way)
Insights
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When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 39% compared to booking last minute.
Insights
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Insights
When to travel
Cheapest • 28% price drop
Most popular
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

Wed, May 20 - Tue, May 26
Delta Logo
11:12 pm - 8:49 am
PDX
-
MKE
7h 37m
1 stop
Delta Logo
5:01 pm - 10:02 pm
MKE
-
PDX
7h 01m
1 stop
$317Delta
Tue, Aug 25 - Tue, Sep 1
United Airlines Logo
7:00 am - 3:04 pm
PDX
-
MKE
6h 04m
1 stop
United Airlines Logo
10:45 am - 5:43 pm
MKE
-
PDX
8h 58m
2 stops
$322United Airlines
Wed, Jun 3 - Sat, Jun 6
United Airlines Logo
11:40 pm - 9:57 am
PDX
-
MKE
8h 17m
1 stop
United Airlines Logo
7:00 pm - 11:53 pm
MKE
-
PDX
6h 53m
1 stop
$325United Airlines
Tue, May 19 - Wed, May 20
United Airlines Logo
2:38 pm - 10:33 pm
PDX
-
MKE
5h 55m
1 stop
United Airlines Logo
2:38 pm - 9:09 pm
MKE
-
PDX
8h 31m
1 stop
$328United Airlines
Sat, May 23 - Thu, May 28
Alaska Airlines Logo
9:44 am - 11:59 pm
PDX
-
MKE
12h 15m
1 stop
Alaska Airlines Logo
4:40 pm - 9:28 pm
MKE
-
PDX
6h 48m
1 stop
$333Alaska Airlines
Tue, Jun 16 - Tue, Jun 23
Southwest Logo
3:40 pm - 12:55 am
PDX
-
MKE
7h 15m
1 stop
Southwest Logo
6:55 pm - 11:50 pm
MKE
-
PDX
6h 55m
1 stop
$348Southwest
Wed, Jun 17 - Wed, Jun 24
American Airlines Logo
10:59 pm - 7:42 am
PDX
-
MKE
6h 43m
1 stop
American Airlines Logo
6:50 pm - 11:47 pm
MKE
-
PDX
6h 57m
1 stop
$357American Airlines
Tue, May 26 - Tue, Jun 2
Southwest Logo
11:55 pm - 10:55 am
PDX
-
MKE
9h 00m
1 stop
Southwest Logo
6:10 am - 1:40 pm
MKE
-
PDX
9h 30m
2 stops
$358Southwest
Tue, Aug 25 - Tue, Sep 1
Southwest Logo
11:30 pm - 11:05 am
PDX
-
MKE
9h 35m
1 stop
Southwest Logo
12:40 pm - 7:50 pm
MKE
-
PDX
9h 10m
2 stops
$359Southwest
Wed, Jun 17 - Wed, Jun 24
American Airlines Logo
10:59 pm - 7:42 am
PDX
-
MKE
6h 43m
1 stop
American Airlines Logo
6:50 pm - 11:47 pm
MKE
-
PDX
6h 57m
1 stop
$363American 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.

How much is a round-trip flight from Portland to Milwaukee?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Milwaukee departing in May.

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 $324 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $570 and $554 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 5 weeks before departure, which saves you about 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$159
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly with an average 15% 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 $159 for a one-way ticket and $317 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Portland to Milwaukee are Southwest and Delta. With an average price for the route of $493 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $436 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
SouthwestOverall score based on 4314 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

very nice blankets and comfortable seats. great service. Great flights.

great experience just at the end, we got in early and there wasn't anyone at the gate for 30 min so we had to just sit on the tarmac

Generally Good. Outbound flight was marred by a continuously s creaming baby. Fortunately the flight was only 90 mins long it would be nice if people traveling with small childres could be centered in one part of the plane. Also, you need to adapt your servey to include a "not applicable " option for things like food and entertainment, which are not offered on shorter flights. I fily Alaska by choice as given all the cirumstances, I fel\el you do a good job.

I was seating in 26A and the children in 27A and B were kicking me non-stop. They kicked me for hours nonstop and the parents refused to get off their phones or correct them. I kindly asked multiple times and got screamed at by the mom that her son is disabled. I told her I get it, but that I matter too and she is responsible for her child. He then kicked me so hard my drink spilled. Not one crew member or other passenger said or did a thing. It was so horrible.

Birding was slow. extremely slow; please do experiments on efficient plane boarding experiences; especially regarding passengers that pass their seat number…

Pretty smooth ride!… a little tight in the back and would’ve loved to had a movie screen… couldn’t beat the price to the West Coast!

I like not much people. Could tell the kids to be quiet.

I liked everything except, I left a brand new Switch 2 on the plane and talking to anybody about it is nearly impossible. I had to fill out a form and hope they get back to me in the next 2 weeks. I really hope they contact me. I saved for that thing for over a year and my son is heart broken.

Fight attendant excellent Food very good, not great Seats were stiff and uncomfortable Flight was overall very nice. Last three flights were burdened with miserably uncomfortable seats. Hard stiff no padding.

The ground crew was very good. They communicated clearly and continued updating. The flight crew was fine. The flight crew on the March 20th flight from MCI to Portland was excellent.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

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

Information on your arrival and departure airports