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$132+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Milwaukee to Oregon

Keep the following information in mind while searching for Milwaukee to Oregon flight deals. Data was last updated September 15, 2025.

Round-trip from

$150
(Priceline)

One-way from

$132
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$348
From Milwaukee-Mitchell to Oregon
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One-way flight from Milwaukee-Mitchell to Oregon
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Highest demand for flights based on searches. 5% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:36 pmMKE - PDX
1 stop6h 36mFrontier
Mon 10/66:05 amPDX - MKE
1 stop11h 14mFrontier
Deal found 9/15$160
This Delta deal was found by Cheapflights users on 9/12. 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.
Fri 11/142:53 pmMKE - PDX
1 stop7h 54mDelta
Wed 11/196:00 amPDX - MKE
1 stop6h 13mDelta
Deal found 9/12$219
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/228:04 pmMKE - PDX
1 stop6h 08mFrontier
Mon 9/296:05 amPDX - MKE
1 stop11h 14mFrontier
Deal found 9/15$258
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/24:33 pmMKE - PDX
1 stop9h 32mAmerican Airlines
Sun 10/55:13 amPDX - MKE
1 stop6h 49mAmerican Airlines
Deal found 9/12$267
This Delta deal was found by Cheapflights users on 9/13. 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.
Sat 10/186:59 pmMKE - BOI
1 stop5h 55mDelta
Tue 10/215:42 amBOI - MKE
1 stop4h 42mDelta
Deal found 9/13$268
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:36 pmMKE - PDX
1 stop6h 36mFrontier
Mon 9/296:05 amPDX - MKE
1 stop11h 14mFrontier
Deal found 9/13$272
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:50 pmMKE - PDX
1 stop15h 21mMultiple Airlines
Thu 10/3012:52 pmPDX - MKE
1 stop28h 27mMultiple Airlines
Deal found 9/15$275
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:35 amMKE - PDX
2 stops11h 00mSouthwest
Tue 10/215:50 amPDX - MKE
1 stop5h 45mSouthwest
Deal found 9/12$278
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/293:56 pmMKE - BOI
1 stop7h 24mAlaska Airlines
Mon 11/36:28 amBOI - MKE
1 stop7h 32mAlaska Airlines
Deal found 9/13$282
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:12 amMKE - BOI
1 stop7h 23mAmerican Airlines
Tue 11/181:25 pmBOI - MKE
1 stop7h 10mAmerican Airlines
Deal found 9/15$283
This Sun Country Air deal was found by Cheapflights users on 9/13. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:27 pmMKE - PDX
1 stop6h 26mSun Country Air
Sat 12/2711:59 pmPDX - MKE
1 stop15h 34mSun Country Air
Deal found 9/13$285
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/75:46 pmMKE - PDX
1 stop7h 43mAmerican Airlines
Sat 10/1111:58 pmPDX - MKE
1 stop8h 35mAmerican Airlines
Deal found 9/13$287

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 September 15, 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

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 11/14

2:53 pm-8:47 pm

1 stop7h 54m

Portland

Tue 11/18

12:35 am-8:15 am

1 stop5h 40m

$219

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Thu 10/2

4:33 pm-12:05 am

1 stop9h 32m

Portland

Sun 10/5

5:13 am-2:02 pm

1 stop6h 49m

$267

MilwaukeeBoise

MKE - BOI

MKEBOI

Milwaukee-Mitchell

Sat 10/18

7:30 am-6:51 pm

2 stops12h 21m

Boise Air Term. Gowen Fld

Tue 10/21

11:12 am-11:55 pm

2 stops11h 43m

$278

MilwaukeeBoise

MKE - BOI

MKEBOI

Milwaukee-Mitchell

Mon 11/10

6:12 am-12:35 pm

1 stop7h 23m

Boise Air Term. Gowen Fld

Tue 11/18

1:25 pm-9:35 pm

1 stop7h 10m

$283

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Wed 10/15

2:04 pm-10:08 pm

1 stop10h 04m

Portland

Mon 10/20

12:40 am-8:19 am

1 stop5h 39m

$287

MilwaukeeBoise

MKE - BOI

MKEBOI

Milwaukee-Mitchell

Wed 10/29

1:10 pm-11:59 pm

2 stops11h 49m

Boise Air Term. Gowen Fld

Mon 11/3

1:39 pm-11:55 pm

1 stop9h 16m

$288

MilwaukeeBoise

MKE - BOI

MKEBOI

Milwaukee-Mitchell

Mon 11/10

12:12 pm-10:07 pm

2 stops10h 55m

Boise Air Term. Gowen Fld

Tue 11/18

1:49 pm-11:56 pm

1 stop9h 07m

$288

MilwaukeeRedmond

MKE - RDM

MKERDM

Milwaukee-Mitchell

Tue 10/14

6:36 am-1:05 pm

1 stop8h 29m

Bend/Redmond

Tue 10/21

1:54 pm-12:20 am

1 stop8h 26m

$299

MilwaukeeRedmond

MKE - RDM

MKERDM

Milwaukee-Mitchell

Sat 10/25

4:30 pm-8:50 pm

1 stop6h 20m

Bend/Redmond

Sat 11/1

5:00 am-5:17 pm

2 stops10h 17m

$304

MilwaukeePortland

MKE - PDX

MKEPDX

Milwaukee-Mitchell

Fri 11/14

3:56 pm-6:04 am

2 stops16h 08m

Portland

Wed 11/19

1:38 pm-3:00 pm

1 stop23h 22m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 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, November is the cheapest month in which you can book a flight from Milwaukee to Oregon (average of $277). Flying from Milwaukee to Oregon in March is currently the most expensive (average of $368). 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 September 15, 2025.

When flying from Milwaukee to Oregon, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 15, 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
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,954 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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, American Airlines, and United Airlines fly from Milwaukee to Oregon in about 6h 20m. The time it takes to get you to your destination can typically vary by up to 3h 12m. There are 1654 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 $132. Sun Country Air flights start at $138 while deals on Hawaiian Airlines start at $149 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 - Boise Air Term. Gowen Fld or Milwaukee-Mitchell - Bend/Redmond 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, November is the cheapest month in which you can book a flight from Milwaukee to Oregon (average of $277). Flying from Milwaukee to Oregon in March is currently the most expensive (average of $368). 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

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Top 8 airlines flying from Milwaukee to Oregon

Discover the top 8 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$231FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$233FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$207Average$422FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$278Average$278FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$278Average$497FlexibilityNo cancel feeOn-time75%
DeltaCheapest$278Average$486FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$278Average$502FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$334Average$476FlexibilityNo cancel feeOn-time63%

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