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$120+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Portland are usually found in September or November, 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 October 23, 2025.

This Delta deal was found by Cheapflights users on 10/21. 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.
Fri 12/54:52 pmMKE - PDX
2 stops9h 24mDelta
Mon 12/811:35 amPDX - MKE
2 stops8h 11mDelta
Deal found 10/21$236
This Southwest deal was found by Cheapflights users on 10/21. 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.
Thu 12/45:05 pmMKE - PDX
1 stop7h 25mSouthwest
Tue 12/95:00 amPDX - MKE
1 stop6h 55mSouthwest
Deal found 10/21$272
This Delta deal was found by Cheapflights users on 10/21. 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 12/411:29 amMKE - PDX
2 stops9h 21mDelta
Mon 12/812:32 amPDX - MKE
1 stop8h 02mDelta
Deal found 10/21$278
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/53:51 pmMKE - PDX
1 stop22h 51mHawaiian Airlines
Fri 12/122:37 pmPDX - MKE
1 stop22h 18mHawaiian Airlines
Deal found 10/20$293
This Alaska Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 12/53:51 pmMKE - PDX
1 stop20h 59mAlaska Airlines
Mon 12/81:34 pmPDX - MKE
1 stop23h 21mAlaska Airlines
Deal found 10/21$294
This Delta deal was found by Cheapflights users on 10/22. 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.
Wed 11/192:42 pmMKE - PDX
2 stops11h 32mDelta
Sun 11/2312:35 amPDX - MKE
1 stop5h 40mDelta
Deal found 10/22$296
This Delta deal was found by Cheapflights users on 10/22. 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 12/116:00 amMKE - PDX
1 stop8h 54mDelta
Sun 12/147:30 pmPDX - MKE
2 stops11h 15mDelta
Deal found 10/22$299
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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 10/22$304
This Delta deal was found by Cheapflights users on 10/21. 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.
Sun 11/236:10 amMKE - PDX
2 stops11h 23mDelta
Fri 11/287:59 pmPDX - MKE
2 stops10h 16mDelta
Deal found 10/21$306

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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$236
(Delta)

One-way from

$120
(Southwest)

Popular in

March

Cheapest in

September

Average price

$408
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. 7% potential increase in price ($32 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 October 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 October 23, 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

5:05 pm-10:30 pm

1 stop7h 25m

Portland

Tue 12/9

5:00 am-1:55 pm

1 stop6h 55m

$272

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Sun 11/23

6:10 am-3:33 pm

2 stops11h 23m

Portland

Fri 11/28

7:59 pm-8:15 am

2 stops10h 16m

$306

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Mon 11/17

1:22 pm-10:41 pm

2 stops11h 19m

Portland

Tue 11/18

7:59 pm-8:41 am

2 stops10h 42m

$314

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 12/19

6:27 pm-10:53 pm

1 stop6h 26m

Portland

Tue 12/23

6:14 pm-6:15 pm

1 stop22h 01m

$315

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 12/5

1:12 pm-10:40 pm

2 stops11h 28m

Portland

Fri 12/12

10:10 pm-10:46 am

1 stop10h 36m

$325

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 11/20

5:45 am-12:49 pm

1 stop9h 04m

Portland

Thu 11/27

5:30 am-4:55 pm

2 stops9h 25m

$332

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Mon 11/17

3:56 pm-8:37 pm

1 stop6h 41m

Portland

Tue 11/18

6:00 am-3:00 pm

1 stop7h 00m

$336

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 11/12

10:16 am-7:35 pm

1 stop11h 19m

Portland

Fri 11/14

7:59 pm-9:45 pm

2 stops23h 46m

$346

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 12/24

7:00 am-12:12 am

1 stop19h 12m

Portland

Sat 1/3

1:51 pm-11:59 pm

1 stop8h 08m

$352

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Tue 12/16

5:40 am-11:25 am

1 stop7h 45m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 18 results
1
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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 October 17, 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, October is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $137). 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 October 23, 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 October 23, 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
11,161 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

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
11,161 reviews
Alaska Airlines
8.0
Very good
11,161 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

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
4,236 reviews
Alaska Airlines
8.0
Very good
11,161 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

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
7,982 reviews
Alaska Airlines
8.0
Very good
11,161 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

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
8,995 reviews
Alaska Airlines
8.0
Very good
11,161 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

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
11,033 reviews
Alaska Airlines
8.0
Very good
11,161 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

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?

    Southwest, Delta, and Sun Country Air can get you from Milwaukee to Portland in just under 6h 26m. Your travel time can differ by up to 4h 57m. 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, October is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $137). 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

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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$110Average$231FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$269Average$413FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$278Average$287FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$278Average$421FlexibilityNo cancel feeOn-time75%
DeltaCheapest$278Average$422FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$306Average$466FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$328Average$447FlexibilityNo cancel feeOn-time63%

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