HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$142+ 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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Milwaukee to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Milwaukee-Mitchell to Portland are usually found in September or October, booked 60 days in advance, depart on a Wednesday or Friday and return on a Tuesday

Find 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 November 13, 2025.

This Delta deal was found by Cheapflights users on 11/12. 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.
Thu 12/44:52 pmMKE - PDX
2 stops9h 24mDelta
Mon 12/87:30 pmPDX - MKE
2 stops13h 04mDelta
Deal found 11/12$274
This Alaska Airlines deal was found by Cheapflights users on 11/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:51 pmMKE - PDX
1 stop19h 41mAlaska Airlines
Mon 12/88:44 pmPDX - MKE
1 stop16h 11mAlaska Airlines
Deal found 11/11$304
This Delta deal was found by Cheapflights users on 11/10. 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.
Tue 12/94:52 pmMKE - PDX
1 stop7h 18mDelta
Tue 12/165:30 amPDX - MKE
2 stops11h 21mDelta
Deal found 11/10$315
This Alaska Airlines deal was found by Cheapflights users on 11/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:51 pmMKE - PDX
1 stop23h 59mAlaska Airlines
Mon 12/155:49 pmPDX - MKE
1 stop19h 06mAlaska Airlines
Deal found 11/12$333
This Delta deal was found by Cheapflights users on 11/12. 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.
Thu 12/111:12 pmMKE - PDX
2 stops11h 28mDelta
Sun 12/1412:32 amPDX - MKE
1 stop8h 02mDelta
Deal found 11/12$335
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/43:11 pmMKE - PDX
1 stop8h 10mAmerican Airlines
Mon 12/81:28 pmPDX - MKE
1 stop7h 37mAmerican Airlines
Deal found 11/12$336
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:51 pmMKE - PDX
1 stop23h 59mAlaska Airlines
Sun 12/145:49 pmPDX - MKE
1 stop19h 06mAlaska Airlines
Deal found 11/13$343
This Delta deal was found by Cheapflights users on 11/13. 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.
Thu 12/114:52 pmMKE - PDX
2 stops9h 23mDelta
Sat 12/1312:32 amPDX - MKE
1 stop8h 02mDelta
Deal found 11/13$348

Cheap 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$274
(Delta)

One-way from

$142
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$421
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. 6% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 13, 2025.
Use the filters below to find and compare flights from Milwaukee to Portland that are best for you.

Fly from

Milwaukee

Fly to

Portland

Route

Depart

Return

Price

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 12/4

4:52 pm-12:16 am

2 stops9h 24m

Portland

Mon 12/8

7:30 pm-10:34 am

2 stops13h 04m

$274

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Tue 12/9

6:00 am-1:13 pm

2 stops9h 13m

Portland

Tue 12/16

7:30 pm-8:45 am

2 stops11h 15m

$274

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 1/29

3:53 pm-8:47 pm

1 stop6h 54m

Portland

Sun 2/1

7:10 am-3:07 pm

1 stop5h 57m

$304

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 1/9

3:53 pm-2:00 pm

1 stop24h 07m

Portland

Fri 1/16

7:10 am-2:57 pm

1 stop5h 47m

$304

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 12/4

3:51 pm-9:32 am

1 stop19h 41m

Portland

Mon 12/8

8:44 pm-2:55 pm

1 stop16h 11m

$304

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 1/9

3:59 pm-12:17 am

2 stops10h 18m

Portland

Fri 1/16

7:37 pm-8:48 am

2 stops11h 11m

$316

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 12/11

11:29 am-5:43 pm

1 stop8h 14m

Portland

Mon 12/15

7:30 pm-8:45 am

2 stops11h 15m

$325

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 12/19

6:27 pm-10:53 pm

1 stop6h 26m

$142

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 12/12

4:52 pm-12:15 am

2 stops9h 23m

$157

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 12/11

1:12 pm-10:40 pm

2 stops11h 28m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 14 results
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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-Portland flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 7, 2025.

The best time to book flights from Milwaukee to Portland is 60 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, April is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $144). Flying from Milwaukee to Portland in May is currently the most expensive (average of $199). 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.

What is the cheapest time of day to fly from MKE to PDX?

Find hourly flight availability from Milwaukee to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 34% on flights from Milwaukee to Portland by exploring options for tickets in the evening.

What is the cheapest day to fly from Milwaukee to Portland?

Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Portland. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Milwaukee to Portland flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 13, 2025.
Read through reviews of airlines operating flights from Milwaukee to Portland, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,288 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Boarding

8.1

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,288 reviews
Alaska Airlines
8.0
Very good
11,288 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Boarding

8.1

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
11,288 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Boarding

8.1

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
8,007 reviews
Alaska Airlines
8.0
Very good
11,288 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Boarding

8.1

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,017 reviews
Alaska Airlines
8.0
Very good
11,288 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Boarding

8.1

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,051 reviews
Alaska Airlines
8.0
Very good
11,288 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Boarding

8.1

Food

7.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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?

    Delta and Alaska Airlines can get you from Milwaukee to Portland in just under 6h 54m. Your travel time can differ by up to 2h 30m. Milwaukee and Portland are separated by a distance of 1712 mi. This flight may include one or multiple stops.

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

    Currently priced at $110, Frontier will fly you from Milwaukee to Portland and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Hawaiian Airlines - these airlines can fly you to your destination from $269 and $278, respectively. Users have found that Frontier is 74% cheaper than the other options available to this destination.

  • 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, April is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $144). Flying from Milwaukee to Portland in May is currently the most expensive (average of $199). 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
Lake Oswego
Beaverton
McMinnville
Hillsboro
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham
Troutdale

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.

Alternative routes for Milwaukee to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Portland flights
Minneapolis to Portland flights
Minneapolis to Boise flights
O'Hare Intl to Boise flights
O'Hare Intl to Eugene flights
Minneapolis to Redmond flights
O'Hare Intl to Redmond flights
Appleton to Portland flights
Madison to Portland flights
Madison to Boise flights
Minneapolis to Eugene flights
Green Bay to Portland flights
Milwaukee to Redmond flights
O'Hare Intl to Medford flights
Milwaukee to Boise flights
Minneapolis to Medford flights
O'Hare Intl to North Bend flights
Wausau to Portland flights
Madison to Eugene flights
Eau Claire to Portland flights
Duluth to Portland flights
Madison to Redmond flights
Milwaukee to Eugene flights
Appleton to Medford flights
Madison to Medford flights
O'Hare Intl to Yakima flights
Milwaukee to Medford flights
Minneapolis to Yakima flights
Minneapolis to North Bend flights
Appleton to Boise flights
Appleton to Eugene flights
La Crosse to Portland flights
Rhinelander to Boise flights
Minneapolis to Pendleton flights
Milwaukee to Yakima flights
Green Bay to Boise flights
Madison to Yakima flights
La Crosse to Redmond flights
Dubuque to Portland flights

Top 7 airlines flying from Milwaukee to Portland

Discover the top 7 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$110Average$250FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$269Average$415FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$278Average$287FlexibilityNo cancel feeOn-time85%
DeltaCheapest$278Average$435FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$291Average$421FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$306Average$465FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$328Average$446FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.