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$157+ Cheap flights from Milwaukee to Portland (MKE - PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
1 adult, Economy
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Cheap flight deals from Milwaukee to Portland

Cheapest flights from Milwaukee to Portland
Explore the most affordable flight options available from Milwaukee to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.

This Frontier deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:29 pm
MKE
-
PDX
1 stop19h 13m
Frontier
Thu 4/2311:48 am
PDX
-
MKE
1 stop27h 46m
Frontier
Deal found 3/18$273
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:37 pm
MKE
-
PDX
1 stop6h 57m
United Airlines
Wed 5/62:41 pm
PDX
-
MKE
1 stop5h 52m
United Airlines
Deal found 3/17$317
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:45 am
MKE
-
PDX
2 stops8h 59m
United Airlines
Tue 4/215:00 am
PDX
-
MKE
1 stop7h 28m
United Airlines
Deal found 3/17$322
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:25 pm
MKE
-
PDX
1 stop9h 10m
United Airlines
Sat 5/162:41 pm
PDX
-
MKE
1 stop5h 49m
United Airlines
Deal found 3/17$325
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:10 am
MKE
-
PDX
2 stops9h 30m
Southwest
Tue 4/215:30 am
PDX
-
MKE
2 stops9h 55m
Southwest
Deal found 3/17$327
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:05 pm
MKE
-
PDX
2 stops8h 55m
Southwest
Wed 5/66:30 am
PDX
-
MKE
1 stop11h 00m
Southwest
Deal found 3/18$328
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/284:05 pm
MKE
-
PDX
1 stop9h 05m
Southwest
Sat 5/29:35 am
PDX
-
MKE
2 stops10h 15m
Southwest
Deal found 3/18$330
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:48 pm
MKE
-
PDX
1 stop7h 05m
Delta
Sun 4/1212:30 am
PDX
-
MKE
1 stop7h 43m
Delta
Deal found 3/17$333
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/274:50 pm
MKE
-
PDX
2 stops10h 05m
Southwest
Wed 4/296:30 am
PDX
-
MKE
1 stop11h 00m
Southwest
Deal found 3/18$336
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:37 pm
MKE
-
PDX
1 stop6h 57m
United Airlines
Sat 5/27:45 pm
PDX
-
MKE
2 stops10h 04m
United Airlines
Deal found 3/19$338
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:40 pm
MKE
-
PDX
1 stop7h 17m
American Airlines
Sat 4/253:16 pm
PDX
-
MKE
1 stop6h 24m
American Airlines
Deal found 3/19$349

Find flight deals from Milwaukee to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$273
(Frontier)

One-way from

$157
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$506
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
Search Deals
From Milwaukee-Mitchell to Portland
Search Deals
One-way flight from Milwaukee-Mitchell to Portland
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 22, 2026.
Use the filters below to find and compare flights from Milwaukee to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 4/29

5:37 pm-10:34 pm

1 stop6h 57m

Portland

Wed 5/6

2:41 pm-10:33 pm

1 stop5h 52m

$317

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Sat 4/11

4:48 pm-9:53 pm

1 stop7h 05m

Portland

Tue 4/14

11:15 pm-8:49 am

1 stop7h 34m

$325

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 5/13

3:51 pm-10:59 pm

1 stop9h 08m

Portland

Sat 5/16

2:41 pm-10:30 pm

1 stop5h 49m

$325

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Sat 4/11

4:48 pm-9:53 pm

1 stop7h 05m

Portland

Sun 4/12

12:30 am-10:13 am

1 stop7h 43m

$333

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 5/13

2:40 pm-9:00 pm

1 stop8h 20m

Portland

Sat 5/16

11:15 am-11:15 pm

2 stops10h 00m

$370

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Mon 4/27

4:50 pm-12:55 am

2 stops10h 05m

Portland

Wed 4/29

11:15 am-9:45 pm

2 stops8h 30m

$375

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 4/8

6:30 am-12:48 pm

1 stop8h 18m

Portland

Wed 5/13

8:11 pm-8:49 am

2 stops10h 38m

$375

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Mon 6/8

5:55 pm-11:34 pm

1 stop7h 39m

Portland

Fri 6/12

10:55 pm-8:41 am

1 stop7h 46m

$405

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Sat 5/2

2:38 pm-9:09 pm

1 stop8h 31m

Portland

Tue 5/5

2:41 pm-10:30 pm

1 stop5h 49m

$415

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 7/22

5:29 pm-12:02 am

1 stop8h 33m

Portland

Wed 7/29

2:25 pm-10:39 pm

1 stop6h 14m

$417

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Compare providers for flights from Milwaukee to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milwaukee to Portland in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Milwaukee-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Milwaukee-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Milwaukee to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Milwaukee with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Milwaukee to Portland?

Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Portland. Price data was last updated on March 13, 2026.

The best time to book flights from Milwaukee to Portland is 77 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Milwaukee to Portland?

Currently, January is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $133). Flying from Milwaukee to Portland in December is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated March 22, 2026.
Read through reviews of airlines operating flights from Milwaukee to Portland, such as Southwest,Alaska Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,091 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,314 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,455 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,489 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Milwaukee to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Milwaukee to Portland?

    United Airlines can get you from Milwaukee to Portland in just under 6h 57m. Your travel time can differ by up to . Milwaukee and Portland are separated by a distance of 1712 mi.

  • What are the cheapest airlines flying from Milwaukee to Portland round-trip?

    Currently priced at $139, Hawaiian Airlines will fly you from Milwaukee to Portland and back. In addition to Hawaiian Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Alaska Airlines - these airlines can fly you to your destination from $236 and $276, respectively. Users have found that Hawaiian Airlines is 67% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Milwaukee to Portland one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $95. Users have also found prices from $98 and $111 on Alaska Airlines and Southwest, respectively.

  • Can I find deals for flights from Milwaukee to Portland that include hotel bookings?

    Yes. In addition to deals on Milwaukee to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Milwaukee to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Milwaukee to Portland.

  • Can I find deals for business class flights from Milwaukee to Portland?

    Yes. Cheapflights offers flight deals from Milwaukee to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Milwaukee to Portland?

    Currently, January is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $133). Flying from Milwaukee to Portland in December is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Beaverton
Depoe Bay
Wilsonville
Stevenson
Tillamook
Pacific City
Astoria

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 6 airlines flying from Milwaukee to Portland

Discover the top 6 airlines that operate flights from Milwaukee to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$139Average$287FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$236Average$383FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$276Average$435FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$278Average$454FlexibilityNo cancel feeOn-time69%
DeltaCheapest$278Average$420FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$319Average$436FlexibilityNo cancel feeOn-time63%

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