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$149+ Cheap flights from Milwaukee (MKE) to Oregon

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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Milwaukee to Oregon

Cheapest flights from Milwaukee to Oregon
Explore the most affordable flight options available from Milwaukee to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/15. 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 12/256:20 amMKE - PDX
1 stop13h 55mSouthwest
Wed 12/315:00 amPDX - MKE
1 stop6h 55mSouthwest
Deal found 12/15$382
This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1810:43 amMKE - BOI
1 stop12h 43mAmerican Airlines
Sat 1/171:58 pmBOI - MKE
1 stop7h 01mAmerican Airlines
Deal found 12/17$495
This Southwest deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:20 amMKE - PDX
1 stop13h 55mSouthwest
Fri 1/24:05 pmPDX - MKE
1 stop6h 00mSouthwest
Deal found 12/17$523
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/258:28 amMKE - RDM
1 stop6h 30mUnited Airlines
Fri 1/25:00 amRDM - MKE
1 stop8h 00mUnited Airlines
Deal found 12/16$541
This Alaska Airlines deal was found by Cheapflights users on 12/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:00 amMKE - BOI
1 stop9h 22mAlaska Airlines
Sun 1/410:47 amBOI - MKE
1 stop12h 12mAlaska Airlines
Deal found 12/17$541
This Southwest deal was found by Cheapflights users on 12/16. 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 12/315:05 pmMKE - PDX
1 stop7h 25mSouthwest
Sat 1/37:10 amPDX - MKE
1 stop6h 40mSouthwest
Deal found 12/16$557
This Southwest deal was found by Cheapflights users on 12/17. 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.
Wed 12/315:05 amMKE - EUG
1 stop10h 45mSouthwest
Sun 1/412:55 pmEUG - MKE
1 stop7h 00mSouthwest
Deal found 12/17$577
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/313:27 pmMKE - PDX
1 stop8h 32mAmerican Airlines
Sun 1/43:02 pmPDX - MKE
1 stop7h 42mAmerican Airlines
Deal found 12/16$582
This Delta deal was found by Cheapflights users on 12/16. 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 12/173:07 pmMKE - PDX
1 stop7h 45mDelta
Thu 12/256:15 amPDX - MKE
1 stop7h 09mDelta
Deal found 12/16$586
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/1812:02 pmMKE - BOI
1 stop11h 57mUnited Airlines
Sat 1/1710:48 amBOI - MKE
2 stops10h 11mUnited Airlines
Deal found 12/17$631
This Delta deal was found by Cheapflights users on 12/17. 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.
Fri 12/197:20 amMKE - BOI
1 stop5h 42mDelta
Sat 1/171:42 pmBOI - MKE
1 stop8h 46mDelta
Deal found 12/17$645
This Delta deal was found by Cheapflights users on 12/16. 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 12/187:31 pmMKE - BOI
1 stop5h 38mDelta
Sat 1/1710:39 amBOI - MKE
2 stops9h 36mDelta
Deal found 12/16$650

Find flight deals from Milwaukee to Oregon

Keep the following information in mind while searching for Milwaukee to Oregon flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$266
(Delta)

One-way from

$149
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$446
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 Oregon
Search Deals
One-way flight from Milwaukee-Mitchell to Oregon
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($24 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 Oregon 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 18, 2025.
Use the filters below to find and compare flights from Milwaukee to Oregon that are best for you.

Fly from

Milwaukee

Fly to

Oregon

Route

Depart

Return

Price

MilwaukeeRedmond

MKE - RDM

MKERDM

Milwaukee-Mitchell

Wed 2/25

1:21 pm-10:45 pm

2 stops11h 24m

Bend/Redmond

Wed 3/4

7:00 am-9:34 pm

2 stops12h 34m

$266

MilwaukeeBoise

MKE - BOI

MKEBOI

Milwaukee-Mitchell

Thu 2/26

3:47 pm-3:08 pm

1 stop24h 21m

Boise Air Term. Gowen Fld

Tue 3/3

6:00 pm-2:51 pm

1 stop19h 51m

$274

MilwaukeeBoise

MKE - BOI

MKEBOI

Milwaukee-Mitchell

Thu 2/26

1:21 pm-9:56 pm

2 stops9h 35m

Boise Air Term. Gowen Fld

Tue 3/3

7:30 am-9:34 pm

2 stops13h 04m

$276

MilwaukeeRedmond

MKE - RDM

MKERDM

Milwaukee-Mitchell

Fri 2/6

3:53 pm-11:52 pm

1 stop9h 59m

Bend/Redmond

Sun 2/8

8:45 am-2:57 pm

1 stop28h 12m

$285

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 2/27

3:47 pm-10:41 pm

1 stop8h 54m

Portland

Sun 3/1

8:30 am-2:51 pm

1 stop28h 21m

$285

MilwaukeeRedmond

MKE - RDM

MKERDM

Milwaukee-Mitchell

Fri 1/16

3:53 pm-11:52 pm

1 stop9h 59m

Bend/Redmond

Wed 1/21

1:34 pm-2:57 pm

1 stop23h 23m

$303

MilwaukeeRedmond

MKE - RDM

MKERDM

Milwaukee-Mitchell

Sat 1/31

11:30 am-10:19 pm

2 stops12h 49m

Bend/Redmond

Tue 2/3

1:16 pm-9:21 pm

1 stop6h 05m

$304

MilwaukeeMedford

MKE - MFR

MKEMFR

Milwaukee-Mitchell

Fri 2/6

3:53 pm-12:43 pm

1 stop22h 50m

Medford

Mon 2/9

5:42 am-2:57 pm

1 stop7h 15m

$304

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 2/18

1:21 pm-8:55 pm

2 stops9h 34m

Portland

Sun 2/22

7:10 am-9:34 pm

2 stops12h 24m

$312

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 2/18

3:47 pm-10:41 pm

1 stop8h 54m

Portland

Sun 2/22

6:00 am-2:51 pm

1 stop6h 51m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 59 results
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Best time to book a flight from Milwaukee to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon 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 Oregon

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

Currently, January is the cheapest month in which you can book a flight from Milwaukee to Oregon (average of $123). Flying from Milwaukee to Oregon 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.

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

Find hourly flight availability from Milwaukee to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

It’s typically best to fly out from Milwaukee to Oregon in the evening. Doing so could potentially save you 40% on the flight price compared to flying at noon, which is usually more expensive.

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

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

Travelers seeking maximum savings on their Milwaukee to Oregon 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.

How much does it cost to fly round-trip from Milwaukee to Oregon?

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated December 18, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Milwaukee to Oregon by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,477 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,250 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,005 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,091 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,054 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

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

  • What airport do you fly from for flights from Milwaukee to Oregon?

    Most people fly from Milwaukee-Mitchell (MKE) if they book a flight from Milwaukee to Oregon. Milwaukee-Mitchell is conveniently located just 6.4 mi from Milwaukee’s city center.

  • How long is the flight from Milwaukee to Oregon?

    Airlines like Delta, Alaska Airlines, and United Airlines fly from Milwaukee to Oregon in about 7h 45m. The time it takes to get you to your destination can typically vary by up to 16h 36m. There are 1712 mi between Milwaukee and Oregon. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $95. Alaska Airlines flights start at $98 while deals on Southwest start at $111 one-way.

  • What are the most popular routes from Milwaukee to Oregon?

    When deciding which route to take from Milwaukee to Oregon consider Milwaukee-Mitchell - Portland, Milwaukee-Mitchell - Bend/Redmond or Milwaukee-Mitchell - Boise Air Term. Gowen Fld as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee to Oregon 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 Oregon?

    Currently, January is the cheapest month in which you can book a flight from Milwaukee to Oregon (average of $123). Flying from Milwaukee to Oregon 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.

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Alternative routes for Milwaukee to Oregon

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 Oregon

Discover the top 7 airlines that operate flights from Milwaukee to Oregon. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$110Average$250FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$269Average$399FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$276Average$475FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$278Average$287FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$278Average$473FlexibilityNo cancel feeOn-time69%
DeltaCheapest$298Average$468FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$328Average$446FlexibilityNo cancel feeOn-time63%

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