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$151+ Cheap flights from Oregon to Milwaukee (MKE)

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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Cheap flight deals from Oregon to Milwaukee

Best flights from Oregon to Milwaukee
Discover carefully curated flight deals from Oregon to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This Delta deal was found by Cheapflights users on 12/30. 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 1/317:10 amPDX - MKE
2 stops12h 05mDelta
Thu 2/57:45 amMKE - PDX
2 stops13h 05mDelta
Deal found 12/30$273
This Alaska Airlines deal was found by Cheapflights users on 12/31. 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 2/126:00 amPDX - MKE
1 stop6h 51mAlaska Airlines
Mon 2/163:47 pmMKE - PDX
1 stop19h 02mAlaska Airlines
Deal found 12/31$285
This United Airlines deal was found by Cheapflights users on 12/31. 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.
Sat 5/212:45 pmMFR - MKE
1 stop6h 57mUnited Airlines
Wed 5/132:58 pmMKE - MFR
1 stop8h 12mUnited Airlines
Deal found 12/31$317
This Delta deal was found by Cheapflights users on 12/31. 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 2/117:10 amPDX - MKE
2 stops12h 20mDelta
Sat 2/143:53 pmMKE - PDX
2 stops8h 55mDelta
Deal found 12/31$280
This Alaska Airlines deal was found by Cheapflights users on 12/31. 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 2/276:00 amPDX - MKE
1 stop6h 51mAlaska Airlines
Thu 3/53:47 pmMKE - PDX
1 stop9h 57mAlaska Airlines
Deal found 12/31$285
This Alaska Airlines deal was found by Cheapflights users on 1/1. 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 2/277:05 amPDX - MKE
1 stop5h 46mAlaska Airlines
Sun 3/13:47 pmMKE - PDX
1 stop19h 02mAlaska Airlines
Deal found 1/1$285
This United Airlines deal was found by Cheapflights users on 12/31. 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 1/285:00 amMFR - MKE
1 stop6h 30mUnited Airlines
Wed 2/48:00 amMKE - MFR
1 stop7h 19mUnited Airlines
Deal found 12/31$317
This Delta deal was found by Cheapflights users on 1/1. 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 1/227:37 pmPDX - MKE
2 stops11h 11mDelta
Wed 1/287:45 amMKE - PDX
2 stops13h 05mDelta
Deal found 1/1$290
This Alaska Airlines deal was found by Cheapflights users on 12/30. 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.
Sat 1/319:30 pmPDX - MKE
1 stop15h 37mAlaska Airlines
Fri 2/63:53 pmMKE - PDX
1 stop6h 54mAlaska Airlines
Deal found 12/30$285
This Delta deal was found by Cheapflights users on 1/1. 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 2/277:35 pmPDX - MKE
2 stops12h 55mDelta
Thu 3/51:21 pmMKE - PDX
2 stops9h 34mDelta
Deal found 1/1$290
This United Airlines deal was found by Cheapflights users on 12/30. 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.
Sat 1/1712:19 pmBOI - MKE
1 stop7h 29mUnited Airlines
Tue 1/202:32 pmMKE - BOI
1 stop9h 25mUnited Airlines
Deal found 12/30$335
This Alaska Airlines deal was found by Cheapflights users on 12/30. 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.
Sat 1/311:38 pmPDX - MKE
1 stop23h 29mAlaska Airlines
Thu 2/53:53 pmMKE - PDX
1 stop6h 54mAlaska Airlines
Deal found 12/30$285
This Delta deal was found by Cheapflights users on 1/1. 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 2/277:35 pmPDX - MKE
2 stops12h 55mDelta
Sun 3/11:21 pmMKE - PDX
2 stops9h 34mDelta
Deal found 1/1$290
This United Airlines deal was found by Cheapflights users on 12/31. 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 1/211:16 pmRDM - MKE
1 stop6h 05mUnited Airlines
Sat 1/248:00 amMKE - RDM
1 stop7h 02mUnited Airlines
Deal found 12/31$353
This Delta deal was found by Cheapflights users on 1/1. 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.
Mon 2/212:35 pmRDM - MKE
1 stop6h 40mDelta
Fri 2/67:45 amMKE - RDM
1 stop6h 10mDelta
Deal found 1/1$293
This Kiwi.com deal was found by Cheapflights users on 12/31. 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.
Tue 5/55:45 amMFR - MKE
1 stop6h 27mAlaska Airlines
Sat 5/167:00 amMKE - MFR
1 stop7h 48mAlaska Airlines
Deal found 12/31$301
This United Airlines deal was found by Cheapflights users on 12/30. 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.
Sat 1/175:00 amEUG - MKE
1 stop7h 22mUnited Airlines
Tue 1/208:00 amMKE - EUG
1 stop7h 07mUnited Airlines
Deal found 12/30$359
This Alaska Airlines deal was found by Cheapflights users on 12/31. 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.
Sat 5/25:45 amMFR - MKE
1 stop6h 58mAlaska Airlines
Sat 5/167:00 amMKE - MFR
1 stop7h 48mAlaska Airlines
Deal found 12/31$302
This Delta deal was found by Cheapflights users on 1/1. 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 2/197:15 amPDX - MKE
2 stops12h 17mDelta
Sun 2/221:21 pmMKE - PDX
2 stops9h 34mDelta
Deal found 1/1$303
This Delta deal was found by Cheapflights users on 12/31. 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 5/26:00 amMFR - MKE
2 stops8h 54mDelta
Wed 5/131:00 pmMKE - MFR
2 stops12h 13mDelta
Deal found 12/31$309
This Alaska Airlines deal was found by Cheapflights users on 12/31. 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.
Sat 5/25:45 amMFR - MKE
1 stop6h 58mAlaska Airlines
Fri 5/157:00 amMKE - MFR
1 stop12h 03mAlaska Airlines
Deal found 12/31$322
This Delta deal was found by Cheapflights users on 12/31. 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 5/56:00 amMFR - MKE
2 stops13h 21mDelta
Tue 5/191:00 pmMKE - MFR
2 stops12h 13mDelta
Deal found 12/31$309
This Delta deal was found by Cheapflights users on 12/31. 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 1/281:05 pmMFR - MKE
1 stop6h 10mDelta
Wed 2/411:03 amMKE - MFR
2 stops7h 37mDelta
Deal found 12/31$314
This United Airlines deal was found by Cheapflights users on 1/1. 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 1/141:16 pmRDM - MKE
1 stop6h 05mUnited Airlines
Sat 1/178:00 amMKE - RDM
1 stop7h 02mUnited Airlines
Deal found 1/1$513
This Delta deal was found by Cheapflights users on 1/1. 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 1/291:00 pmBOI - MKE
1 stop7h 15mDelta
Thu 2/57:45 amMKE - BOI
2 stops11h 43mDelta
Deal found 1/1$328
This Alaska Airlines deal was found by Cheapflights users on 1/1. 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 7/11:26 pmRDM - MKE
1 stop8h 33mAlaska Airlines
Sat 7/116:24 amMKE - RDM
1 stop8h 08mAlaska Airlines
Deal found 1/1$445
This Delta deal was found by Cheapflights users on 12/31. 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 5/56:00 amMFR - MKE
2 stops13h 21mDelta
Sat 5/163:15 pmMKE - MFR
2 stops9h 58mDelta
Deal found 12/31$361
This Delta deal was found by Cheapflights users on 12/31. 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 5/211:14 amMFR - MKE
2 stops9h 32mDelta
Sat 5/163:15 pmMKE - MFR
2 stops9h 58mDelta
Deal found 12/31$361
This Delta deal was found by Cheapflights users on 1/1. 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 1/1612:37 pmEUG - MKE
1 stop6h 38mDelta
Tue 1/207:45 amMKE - EUG
1 stop6h 09mDelta
Deal found 1/1$411
This Delta deal was found by Cheapflights users on 1/1. 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 1/81:00 pmBOI - MKE
1 stop7h 15mDelta
Sun 1/187:45 amMKE - BOI
1 stop5h 24mDelta
Deal found 1/1$491

Find flight deals from Oregon to Milwaukee

Keep the following information in mind while searching for Oregon to Milwaukee flight deals. Data was last updated January 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$271
(Delta)

One-way from

$151
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$338
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
Search Deals
From Oregon to Milwaukee-Mitchell
Search Deals
One-way flight from Oregon to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Milwaukee 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 January 2, 2026.
Use the filters below to find and compare flights from Oregon to Milwaukee that are best for you.

Fly from

Oregon

Fly to

Milwaukee

Route

Depart

Return

Price

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 1/31

7:10 am-9:15 pm

2 stops12h 05m

Milwaukee-Mitchell

Thu 2/5

7:45 am-6:50 pm

2 stops13h 05m

$273

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 2/11

7:10 am-9:30 pm

2 stops12h 20m

Milwaukee-Mitchell

Sat 2/14

3:53 pm-10:48 pm

2 stops8h 55m

$280

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 2/12

6:00 am-2:51 pm

1 stop6h 51m

Milwaukee-Mitchell

Mon 2/16

3:47 pm-8:49 am

1 stop19h 02m

$285

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 2/27

6:00 am-2:51 pm

1 stop6h 51m

Milwaukee-Mitchell

Thu 3/5

3:47 pm-11:44 pm

1 stop9h 57m

$285

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 2/27

7:05 am-2:51 pm

1 stop5h 46m

Milwaukee-Mitchell

Sun 3/1

3:47 pm-8:49 am

1 stop19h 02m

$285

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 1/31

9:30 pm-3:07 pm

1 stop15h 37m

Milwaukee-Mitchell

Fri 2/6

3:53 pm-8:47 pm

1 stop6h 54m

$285

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 1/31

1:38 pm-3:07 pm

1 stop23h 29m

Milwaukee-Mitchell

Thu 2/5

3:53 pm-8:47 pm

1 stop6h 54m

$285

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 1/22

7:37 pm-8:48 am

2 stops11h 11m

Milwaukee-Mitchell

Wed 1/28

7:45 am-6:50 pm

2 stops13h 05m

$290

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 2/27

7:35 pm-10:30 am

2 stops12h 55m

Milwaukee-Mitchell

Thu 3/5

1:21 pm-8:55 pm

2 stops9h 34m

$290

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 2/27

7:35 pm-10:30 am

2 stops12h 55m

Milwaukee-Mitchell

Sun 3/1

1:21 pm-8:55 pm

2 stops9h 34m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 54 results
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Best time to book a flight from Oregon to Milwaukee

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

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

Currently, August is the cheapest month in which you can book a flight from Oregon to Milwaukee (average of $88). Flying from Oregon to Milwaukee in March is currently the most expensive (average of $244). 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.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Milwaukee. 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 into for flights to Milwaukee from Oregon?

    If you book a flight to Milwaukee from Oregon, you will be flying to Milwaukee-Mitchell, which is the city’s only airport. Milwaukee-Mitchell (MKE) is located 6.4 mi from the center of Milwaukee.

  • How long is the flight from Oregon to Milwaukee?

    Departing from Oregon to Milwaukee will take you 6h 51m. The distance from Oregon to Milwaukee is about 1712 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $139 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $139 and $153, respectively.

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

    Most travelers choose Portland - Milwaukee-Mitchell, Boise Air Term. Gowen Fld - Milwaukee-Mitchell or Medford - Milwaukee-Mitchell when deciding on the best route from Oregon to Milwaukee.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Oregon to Milwaukee (average of $88). Flying from Oregon to Milwaukee in March is currently the most expensive (average of $244). 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 Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
Wauwatosa

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Alternative routes for Oregon to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Oregon to Milwaukee

Discover the top 5 airlines that operate flights from Oregon to Milwaukee. 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 January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$533FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$436FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$242Average$469FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$278Average$460FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$304Average$459FlexibilityNo cancel feeOn-time69%

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