PDX - MKE

$157 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 10/5. 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

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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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, Oct 23 - Mon, Oct 27
Frontier Logo
12:43 pm - 7:18 pmPDX-MKE
28h 35m1 stop
Frontier Logo
8:04 pm - 11:56 amMKE-PDX
17h 52m1 stop
$164Frontier
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Thu, Nov 13 - Mon, Nov 17
Frontier Logo
12:52 pm - 7:19 pmPDX-MKE
28h 27m1 stop
Frontier Logo
8:04 pm - 11:56 amMKE-PDX
17h 52m1 stop
$167Frontier
Find Deal
Mon, Sep 29 - Fri, Oct 3
Frontier Logo
6:05 am - 7:19 pmPDX-MKE
11h 14m1 stop
Frontier Logo
7:36 pm - 12:12 amMKE-PDX
6h 36m1 stop
$242Frontier
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Tue, Nov 11 - Wed, Nov 19
Delta Logo
7:59 pm - 8:15 amPDX-MKE
10h 16m2 stops
Delta Logo
9:10 am - 7:19 pmMKE-PDX
12h 09m2 stops
$312Delta
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Mon, Nov 10 - Tue, Nov 18
Delta Logo
12:35 am - 8:15 amPDX-MKE
5h 40m1 stop
Delta Logo
12:12 pm - 10:41 pmMKE-PDX
12h 29m2 stops
$314Delta
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Wed, Dec 3 - Wed, Dec 10
United Airlines Logo
5:00 am - 1:34 pmPDX-MKE
6h 34m1 stop
United Airlines Logo
3:15 pm - 10:52 pmMKE-PDX
9h 37m2 stops
$322United Airlines
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Sat, Oct 4 - Sat, Oct 11
American Airlines Logo
5:16 am - 2:20 pmPDX-MKE
7h 04m1 stop
American Airlines Logo
5:25 am - 9:31 amMKE-PDX
6h 06m1 stop
$337American Airlines
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Fri, Oct 10 - Tue, Oct 14
United Airlines Logo
4:07 pm - 11:59 pmPDX-MKE
5h 52m1 stop
United Airlines Logo
10:50 am - 3:30 pmMKE-PDX
6h 40m1 stop
$348United Airlines
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Fri, Nov 7 - Tue, Nov 11
Southwest Logo
12:45 pm - 12:05 amPDX-MKE
9h 20m1 stop
Southwest Logo
5:40 am - 11:25 amMKE-PDX
7h 45m1 stop
$353Southwest
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Fri, Nov 7 - Tue, Nov 11
Southwest Logo
12:50 pm - 12:05 amPDX-MKE
9h 15m2 stops
Southwest Logo
5:40 am - 11:25 amMKE-PDX
7h 45m1 stop
$382Southwest
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $164 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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
April
Cheapest • 20% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$164
Overall average: $521
Frontier
Thu 10/23Mon 10/27
PDX - MKE • 1 stop
Cheapest one-way
$157
Typical prices: $170-289
Frontier
Sun 10/5
PDX - MKE • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Milwaukee!
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 April, where tickets cost $361 (return) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $530 and $521 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 seasonFebruary
Cheapest flight$157
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 9% 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 $157 for a one-way ticket and $164 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?

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

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

    The two airlines most popular with KAYAK users for flights from Portland to Milwaukee are Southwest and Alaska Airlines. With an average price for the route of $534 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $439 and an overall rating of 8.0.

  • 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 10000 reviews
8.5Crew
7.0Entertainment
7.1Food
8.1Boarding
7.8Comfort
Airline reviews

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

10.0 ExcellentAnonymous, Sep 2025PDX - MCI
Read more Alaska Airlines reviews

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

Staff inside Portland terminal were rude, made us fell rushed and not at all accommodating to seniors. For this alone I will probably never booked from them again.

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

I booked a round trip. I ordered a lunch going and a lunch for the return but got both lunches going. Could have been my error. Both lunches were good.

Well the flight being delayed multiple time really was frustrating. But the crew and flight was good.

generally good. No snacks or drinks on the flight 3379 from Portland to San Jose, CA. Sad.

Everything except for the lack of a choice of the snack provided was great.

I like the friendliness of the staff. The food choices were OK. I wish there was more options. The entertainment through the movie portal was alright.

First time flying with Alaska, and it went great. Thank you for a great experience flying to PDX.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

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

Information on your arrival and departure airports

Compare transportation modes for Portland to Milwaukee

Transportation modeAverage priceAverage duration
Flights5h 40m
Trains$50644h 12m

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