PWM - MKE

$183 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 4/9. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$340
Overall average: $547
United Airlines
Wed 4/22Tue 4/28
PWM - MKE • 1 stop
Cheapest one-way
$183
Typical prices: $166-$255
Delta
Thu 4/9
PWM - MKE • 1 stop
Top airlines
Cheapest • from $340 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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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
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Insights
Top layover airports
Cheapest • Avg $341 (round-trip)
Shortest trip • 4h 29m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 37% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Milwaukee (PWM-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, Apr 22 - Tue, Apr 28
United Airlines Logo
4:28 pm - 9:23 pm
PWM
-
MKE
5h 55m
1 stop
United Airlines Logo
9:43 am - 6:37 pm
MKE
-
PWM
7h 54m
2 stops
$340United Airlines
Wed, Apr 22 - Tue, Apr 28
American Airlines Logo
6:00 am - 12:32 pm
PWM
-
MKE
7h 32m
1 stop
American Airlines Logo
4:26 pm - 12:13 am
MKE
-
PWM
6h 47m
1 stop
$343American Airlines
Mon, May 18 - Sun, May 24
Delta Logo
2:38 pm - 9:52 pm
PWM
-
MKE
8h 14m
1 stop
Delta Logo
7:00 am - 12:00 pm
MKE
-
PWM
4h 00m
1 stop
$386Delta
Thu, May 7 - Sun, May 10
Southwest Logo
4:50 pm - 11:10 pm
PWM
-
MKE
7h 20m
1 stop
Southwest Logo
4:45 pm - 12:05 am
MKE
-
PWM
6h 20m
2 stops
$391Southwest
Tue, Apr 7 - Wed, Apr 8
United Airlines Logo
4:28 pm - 9:49 pm
PWM
-
MKE
6h 21m
1 stop
United Airlines Logo
8:30 am - 2:20 pm
MKE
-
PWM
4h 50m
1 stop
$405United Airlines
Fri, Apr 24 - Mon, Apr 27
Delta Logo
5:26 pm - 9:30 pm
PWM
-
MKE
5h 04m
1 stop
Delta Logo
5:56 pm - 11:24 pm
MKE
-
PWM
4h 28m
1 stop
$407Delta
Tue, Apr 7 - Wed, Apr 8
United Airlines Logo
6:33 pm - 10:30 pm
PWM
-
MKE
4h 57m
1 stop
United Airlines Logo
7:50 am - 6:37 pm
MKE
-
PWM
9h 47m
2 stops
$410United Airlines
Thu, Jul 9 - Wed, Jul 15
United Airlines Logo
6:00 am - 11:08 am
PWM
-
MKE
6h 08m
1 stop
United Airlines Logo
1:30 pm - 11:51 pm
MKE
-
PWM
9h 21m
2 stops
$412United Airlines
Sun, Apr 12 - Fri, Apr 17
Delta Logo
5:23 am - 11:03 am
PWM
-
MKE
6h 40m
1 stop
Delta Logo
2:50 pm - 11:23 pm
MKE
-
PWM
7h 33m
1 stop
$417Delta
Mon, May 11 - Fri, May 15
Southwest Logo
2:50 pm - 10:15 pm
PWM
-
MKE
8h 25m
2 stops
Southwest Logo
3:30 pm - 11:25 pm
MKE
-
PWM
6h 55m
1 stop
$422Southwest
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 November, where tickets cost $312 (return) on average. On the other hand, the most expensive months are September and August, where the average cost of round-trip tickets is $756 and $672 respectively.

Good to know

Low seasonFebruary
Cheapest flight$183
Best time to beat the crowds with an average 31% drop 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

  • 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 $183 for a one-way ticket and $340 for a round-trip.

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

    No, a passport isn't needed to fly from Portland to Milwaukee. However, local authorities might ask for an official ID.

  • 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, SkyTeam, and oneworld 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 $431 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 $487 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.

Reviews of the top 4 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 4319 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

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 had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

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

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

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.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

They put me on an earlier and I got home sooner

Not good. One of my luggage is missing. And until now they can’t find it

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

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

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

Information on your arrival and departure airports