PDX - MKE

$136 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 4/23. 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
$239
Overall average: $375
Frontier
Thu 4/23Mon 4/27
PDX - MKE • 1 stop
Cheapest one-way
$136
Typical prices: $199-$325
Frontier
Thu 4/23
PDX - MKE • 1 stop
Top airlines
Cheapest • from $239 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Milwaukee. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $304 (round-trip)
Shortest trip • 5h 57m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 27% price drop
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

Thu, Apr 23 - Mon, Apr 27
Frontier Logo
11:48 am - 5:34 pm
PDX
-
MKE
27h 46m
1 stop
Frontier Logo
5:05 pm - 11:52 am
MKE
-
PDX
20h 47m
1 stop
$239Frontier
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
11:48 am - 5:34 pm
PDX
-
MKE
27h 46m
1 stop
Frontier Logo
5:05 pm - 11:52 am
MKE
-
PDX
20h 47m
1 stop
$241Frontier
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
11:48 am - 5:34 pm
PDX
-
MKE
27h 46m
1 stop
Frontier Logo
5:05 pm - 11:52 am
MKE
-
PDX
20h 47m
1 stop
$242Frontier
Wed, May 13 - Sat, May 16
Delta Logo
6:00 am - 3:09 pm
PDX
-
MKE
7h 09m
1 stop
Delta Logo
5:00 pm - 10:02 pm
MKE
-
PDX
7h 02m
1 stop
$277Delta
Sat, Apr 11 - Sat, Apr 18
United Airlines Logo
5:00 am - 2:28 pm
PDX
-
MKE
7h 28m
1 stop
United Airlines Logo
10:45 am - 5:45 pm
MKE
-
PDX
9h 00m
2 stops
$282United Airlines
Sat, May 2 - Tue, May 5
Southwest Logo
9:35 am - 9:50 pm
PDX
-
MKE
10h 15m
2 stops
Southwest Logo
4:05 pm - 11:00 pm
MKE
-
PDX
8h 55m
2 stops
$287Southwest
Fri, Apr 3 - Sat, May 2
Delta Logo
12:30 am - 10:11 am
PDX
-
MKE
7h 41m
1 stop
Delta Logo
5:05 pm - 9:42 pm
MKE
-
PDX
6h 37m
1 stop
$297Delta
Thu, May 14 - Sat, May 16
Delta Logo
6:15 am - 4:51 pm
PDX
-
MKE
8h 36m
1 stop
Delta Logo
5:00 pm - 10:02 pm
MKE
-
PDX
7h 02m
1 stop
$305Delta
Tue, Apr 7 - Tue, Apr 21
Southwest Logo
11:55 pm - 10:55 am
PDX
-
MKE
9h 00m
1 stop
Southwest Logo
5:50 am - 12:55 pm
MKE
-
PDX
9h 05m
2 stops
$308Southwest
Tue, Apr 14 - Thu, Apr 16
Southwest Logo
5:30 am - 5:25 pm
PDX
-
MKE
9h 55m
2 stops
Southwest Logo
4:50 pm - 12:10 am
MKE
-
PDX
9h 20m
1 stop
$316Southwest
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 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 $567 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 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$136
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 4% 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 $136 for a one-way ticket and $239 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 $509 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 $427 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 4320 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
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 ?

Never got on because first part of trip was cancelled and we have no idea when we will get rebooked…

Wonderful as always! Pleasant staff, smooth ride, and timely departure.

Everything ran like it should. Staff was professional. Looking forward to flying with them again.

Liked the attention and speed when getting wheelchair..........Was assured by phone that my needs would be taken care of and they were with my name.

The seats were spacious and comfortable. Even in basic economy. However, the flight boarded 30 minutes late.

Alaska used to be a top notch airline. With it's growth it is now in line with the big airlines. Not bad, not great.

Great. I did have a little issue getting into the Lounge, which is likely more an American Airlines issue. I did not carry my physical AAdvantage Executive credit card with me on this trip, which Admirals Club membership is a part of the benefits of having this card. The instructions on the AA website and the Citi cards website make it seem like you don't need the physical card, as both sites state you can enter with your boarding pass and driver's license. But both lounges said you were required to present the physical card (and not the digital version, via Apple Pay), as only the physical card says "Admirals Club" on the back.I also do not have a physical Admirals Club membership card, so while both lounges eventually let me in, both denied me entrance initially for this reason.

Everything from the time I booked my flight through to the end when I got home was smooth and wonderful. Service was great, the flight attendants were attentive and there were no outstanding delays.

Delayed and no entertainment? I also forgot my headphones and immediately reported it and have not heard back yet.

The crew was very friendly. Boarding was quick and efficient.

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 Portland to Milwaukee

Information on your arrival and departure airports