PDX - MKE

$159 Find Cheap Flights from Portland to Milwaukee - Compare and Save

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 9/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$310
Typical prices: $322-$497
Alaska Airlines
Thu 11/12Mon 11/16
PDX - MKE • 1 stop
Cheapest one-way
$159
Typical prices: $268-$325
American Airlines
Thu 9/24
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 $305 (round-trip)
Shortest trip • 5h 48m (one-way)
Insights
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When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 48% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
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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, Nov 12 - Mon, Nov 16
Alaska Airlines Logo
8:05 am - 3:48 pm
PDX
-
MKE
5h 43m
1 stop
Alaska Airlines Logo
4:44 pm - 9:50 am
MKE
-
PDX
19h 06m
2 stops
$310Alaska Airlines
Tue, Oct 6 - Tue, Oct 20
American Airlines Logo
7:30 am - 4:57 pm
PDX
-
MKE
7h 27m
1 stop
American Airlines Logo
7:14 am - 1:32 pm
MKE
-
PDX
8h 18m
1 stop
$317American Airlines
Wed, Sep 16 - Tue, Sep 29
Southwest Logo
5:50 am - 4:40 pm
PDX
-
MKE
8h 50m
1 stop
Southwest Logo
6:20 am - 10:50 am
MKE
-
PDX
6h 30m
1 stop
$317Southwest
Wed, Dec 16 - Wed, Jan 6
Southwest Logo
1:00 pm - 11:05 pm
PDX
-
MKE
8h 05m
1 stop
Southwest Logo
6:00 am - 12:40 pm
MKE
-
PDX
8h 40m
1 stop
$317Southwest
Mon, Oct 26 - Thu, Nov 5
Delta Logo
11:00 pm - 9:11 am
PDX
-
MKE
8h 11m
1 stop
Delta Logo
5:30 am - 1:38 pm
MKE
-
PDX
10h 08m
1 stop
$317Delta
Tue, Aug 25 - Wed, Sep 2
Delta Logo
12:35 am - 8:40 am
PDX
-
MKE
6h 05m
1 stop
Delta Logo
5:34 am - 12:58 pm
MKE
-
PDX
9h 24m
1 stop
$317Delta
Thu, Aug 27 - Thu, Sep 3
United Airlines Logo
2:27 pm - 10:36 pm
PDX
-
MKE
6h 09m
1 stop
United Airlines Logo
5:00 am - 9:29 am
MKE
-
PDX
6h 29m
1 stop
$317United Airlines
Thu, Oct 1 - Tue, Oct 6
United Airlines Logo
11:59 pm - 10:05 am
PDX
-
MKE
8h 06m
1 stop
United Airlines Logo
5:00 am - 9:31 am
MKE
-
PDX
6h 31m
1 stop
$317United Airlines
Thu, Sep 17 - Tue, Sep 22
American Airlines Logo
11:08 pm - 8:01 am
PDX
-
MKE
6h 53m
1 stop
American Airlines Logo
5:43 pm - 11:23 pm
MKE
-
PDX
7h 40m
1 stop
$317American Airlines
Tue, Oct 27 - Tue, Nov 3
Alaska Airlines Logo
6:09 am - 4:19 pm
PDX
-
MKE
8h 10m
1 stop
Alaska Airlines Logo
4:44 pm - 9:50 am
MKE
-
PDX
19h 06m
2 stops
$325Alaska 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 November.

Flight prices are below average for this route right now.

Flights to Milwaukee from Portland usually cost between $344 and $536 in November.
The lowest price found in the past 5 days was $310 on Alaska Airlines (Nov 12-Nov 16).

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 June and February, where the average cost of round-trip tickets is $576 and $570 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 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low season

February

Cheapest flight

$159
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 23% 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 5 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 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 $544 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 $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 4228 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

8.0 ExcellentSean, Jul 2026
HOU - LGB
Read more Southwest reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

Slow boarding, limited food and drink portions. Bad delays and turbulence

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was really nice! I appreciate the gate attendant allowing families with small children to board early on in the process… that was very helpful! The internet service didn’t work with the app I was trying to use even though I paid the $8… other than that it was great! Oh and I should’ve asked for the whole cranberry cocktail can. That cup was about 2 sips…

I liked the boarding process with our loading group and numbers. I disliked that I couldn't guarantee our seats together. I didn't like that the Internet costs $8/ flight, but did love all the inflight options available through their app. I disliked no charging station at my seat for a 3+ hour flight.

Great! Although the flight was about 40 minutes delayed, the crew did a good job getting everything boarded quickly and efficiently.

I would love it if Alaska Airlines brought back the complimentary beverage service on short flights

the flight was fine, But I paid extra for an Aisle seat both planes and did not get what I paid for when you pay an extra almost $80 and do not get the desired seats it was frustrating I don't fly much because of my legs need more room. thank you for your attention to this

Flight was delayed hour and a half. Gate was changed 3 times. After boarding, sat in airplane for another hour while mechanic checked windshield. Total of 2 1/2 hrs behind schedule. Very tiring since I had ben up since 4 am to complete the flight from Honolulu to Milwaukee.

Our seat assignments were mysteriously changed such that our boarding was delayed when they tried to fix it, but to no avail. It took more than 15 min. before we sat down. Then the catering delayed our plane for 35 min.

The flight was delayed by over an hour with no explanation.

Alaska is a great airline, consistent, on time and friendly employees

Food was just ok..had snack box :( Crew was very nice

Boarding took longer, to shuttle to plane. Crew/pilot were great.

I was a little hesitant at first because I never flew on Alaska Airlines before. However at the time of me booking; this airline was one of few that were affordable & had a much needed direct flight option. I was more relieved when I got to the airport & saw that my local relatives chose the same flights. Also, on the flight to Seattle I chatted with a gentleman who flies more frequently than I do & gave Alaska Airlines a higher rating over competing airlines.

The Alaska employees in Milwaukee and MKE to SEA were top notch, very nice and polite. Seattle and SEA to MKE, not so much. I spent a lot to upgrade to 1st, and other than a little more seat width, it was a waste of money. Both legs of the flight, the seat bottom cushion sloped forward and I kept sliding out of my seat with every little bump, so I got no rest at all. MKE to SEA, the food was awful. If I had known that I was going to get a bowl of sawdust and dried rotten fruit for a meal. I would have stayed coach and saved a bundle of money. The cabin crew was excellent however. Alaska needs to enforce the rule that the seats at the gate stay open for passengers. I can't blame Alaska for the rude treatment of TSA swine, but they can make sure a hundred people get seats to wait an hour for their flights because a hundred jerks need to take every available seat for their bags and water bottles. The food from SEA to MKE was much better, but the cabin crew was not very pleasant. To top it all off, I found out that the woman seated next to me paid a lot less for the upgrade than I did. After arriving at MKE, everyone waited at least forty five minutes for our bags to arrive in a completely empty airport. So much for the promise of twenty minutes to get bags. In summary, the upgrade to first class wasn't worth the high price on Alaska. When I pay that much, I expect better service and treatment.

We got stuck on the tarmac taxiing after landing early so we didn’t get off the plane until an hour later than we thought we would

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

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

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

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.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

We had a 90 minute delay due to equipment failure that was detected just before we took off. United rebooked my connecting flight.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

Poor seating comfort, seat cushion too thin, very uncomfortable. My luggage didi not make the flight due to equipment change. At least. United had it delivered the next day. I was without my toilet items for one day.

Flight cancelled because of the grounded 737s. United was good about it and got us onto a later Alaska Airlines flight to Oakland (not San Francisco as originally intended). Had to go through security again and my wife dropped her MacBook Pro, which broke, a $2,500 whoopsie. But we made it home.

Luggage took too long go get off plane in Knoxville. Was almost 45 minutes after the flight landed.

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

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

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

Very poor delay in dfw was really bad n long

I didn't like that my paid for seat was changed 2 hours before my flight.

The gate changed over 6 times in the 4 hours before this flight having us walking all over and back again. The agent told me that the American app and the airport monitors are not reliable and I should Google the flight number for accurate flight information! Shocking tip but the gate still kept changing anyway and then the flight was delayed an hour because of another maintenance issue. Not a great experience.

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

Information on your arrival and departure airports