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$92+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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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

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 December 4, 2025.

This United Airlines deal was found by Cheapflights users on 12/4. 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.
Thu 12/254:11 pmMKE - PDX
1 stop8h 48mUnited Airlines
Mon 1/121:24 pmPDX - MKE
1 stop5h 57mUnited Airlines
Deal found 12/4$384
This Southwest deal was found by Cheapflights users on 12/4. 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 12/2510:30 amMKE - PDX
2 stops9h 20mSouthwest
Mon 1/126:45 amPDX - MKE
2 stops9h 50mSouthwest
Deal found 12/4$411
This Southwest deal was found by Cheapflights users on 12/2. 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 12/246:10 pmMKE - PDX
1 stop6h 25mSouthwest
Mon 12/299:00 pmPDX - MKE
1 stop12h 10mSouthwest
Deal found 12/2$426
This Delta deal was found by Cheapflights users on 12/3. 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 12/2411:08 amMKE - PDX
2 stops11h 28mDelta
Tue 12/306:15 amPDX - MKE
1 stop8h 28mDelta
Deal found 12/3$429
This United Airlines deal was found by Cheapflights users on 12/3. 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 12/244:11 pmMKE - PDX
1 stop6h 56mUnited Airlines
Tue 12/3012:54 pmPDX - MKE
1 stop7h 21mUnited Airlines
Deal found 12/3$431
This Southwest deal was found by Cheapflights users on 12/4. 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 12/2510:30 amMKE - PDX
2 stops9h 20mSouthwest
Wed 12/312:35 pmPDX - MKE
1 stop5h 25mSouthwest
Deal found 12/4$446
This Expedia deal was found by Cheapflights users on 12/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:27 pmMKE - PDX
1 stop6h 26mMultiple Airlines
Tue 12/233:59 pmPDX - MKE
1 stop6h 00mMultiple Airlines
Deal found 12/3$455
This Southwest deal was found by Cheapflights users on 12/4. 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 12/2510:30 amMKE - PDX
2 stops9h 20mSouthwest
Thu 1/15:00 amPDX - MKE
1 stop6h 55mSouthwest
Deal found 12/4$456
This Southwest deal was found by Cheapflights users on 12/2. 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 12/175:05 pmMKE - PDX
1 stop7h 25mSouthwest
Tue 12/239:00 pmPDX - MKE
1 stop12h 20mSouthwest
Deal found 12/2$467
This Southwest deal was found by Cheapflights users on 12/3. 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.
Fri 12/268:15 pmMKE - PDX
1 stop6h 10mSouthwest
Wed 1/146:20 amPDX - MKE
1 stop5h 40mSouthwest
Deal found 12/3$472

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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$183
(Alaska Airlines)

One-way from

$92
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$460
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 ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 4, 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

Tue 1/13

7:45 am-12:32 pm

1 stop6h 47m

Portland

Wed 1/14

1:53 pm-9:30 pm

1 stop5h 37m

$207

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 1/29

3:53 pm-11:32 pm

1 stop9h 39m

Portland

Wed 2/4

6:00 am-3:57 pm

1 stop7h 57m

$210

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 2/5

7:45 am-6:50 pm

2 stops13h 05m

Portland

Wed 2/11

7:10 am-9:30 pm

2 stops12h 20m

$236

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 1/29

8:00 am-1:45 pm

1 stop7h 45m

Portland

Wed 2/4

1:24 pm-10:56 pm

2 stops7h 32m

$242

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 1/29

5:40 pm-10:15 pm

1 stop6h 35m

Portland

Wed 2/4

6:20 am-6:25 pm

2 stops10h 05m

$250

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 1/9

3:53 pm-10:46 pm

1 stop8h 53m

Portland

Mon 1/12

7:10 am-2:57 pm

1 stop5h 47m

$262

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Mon 1/5

3:05 pm-9:50 am

1 stop20h 45m

Portland

Wed 1/7

5:35 pm-2:57 pm

1 stop19h 22m

$274

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 1/29

3:53 pm-4:50 pm

2 stops26h 57m

Portland

Thu 2/5

7:10 am-2:57 pm

1 stop5h 47m

$278

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 1/21

1:04 pm-8:27 pm

1 stop9h 23m

Portland

Sun 1/25

12:35 pm-9:59 pm

1 stop7h 24m

$283

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 1/29

6:40 am-6:50 pm

2 stops14h 10m

Portland

Thu 2/5

7:37 pm-8:48 am

2 stops11h 11m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 16 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 December.
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 28, 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 $145). 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 December 4, 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 December 4, 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
11,402 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Alaska Airlines
8.0
Very good
11,402 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Southwest
8.0
Very good
4,250 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Delta
7.9
Good
8,011 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
United Airlines
7.4
Good
9,066 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
American Airlines
7.2
Good
11,047 reviews
Alaska Airlines
8.0
Very good
11,402 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.

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, American Airlines, and United Airlines can get you from Milwaukee to Portland in just under 6h 47m. Your travel time can differ by up to 2h 52m. 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 Hawaiian Airlines and American Airlines - these airlines can fly you to your destination from $139 and $269, respectively. Users have found that Frontier is 74% 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, April is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $145). 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
Troutdale
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Milwaukee to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$110Average$250FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$269Average$413FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$276Average$420FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$278Average$287FlexibilityNo cancel feeOn-time85%
DeltaCheapest$302Average$440FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$306Average$465FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$328Average$439FlexibilityNo cancel feeOn-time63%

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