Milwaukee

$165+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jun 14 — Jun 211
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Cheap flight deals from Oregon to Milwaukee

Cheapest flights from Oregon to Milwaukee
Explore the most affordable flight options available from Oregon to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.

This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 9/911:55 am
PDX
-
MKE
1 stop7h 15m
American Airlines
Tue 9/1512:22 pm
MKE
-
PDX
1 stop8h 39m
American Airlines
Deal found 5/13$329
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:51 am
PDX
-
MKE
1 stop8h 05m
United Airlines
Sat 6/61:30 pm
MKE
-
PDX
1 stop7h 17m
United Airlines
Deal found 5/13$342
This Southwest deal was found by Cheapflights users on 5/12. 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 9/26:35 am
PDX
-
MKE
2 stops8h 05m
Southwest
Sat 9/56:15 am
MKE
-
PDX
1 stop6h 25m
Southwest
Deal found 5/12$347
This Southwest deal was found by Cheapflights users on 5/12. 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 7/810:40 am
PDX
-
MKE
2 stops9h 35m
Southwest
Wed 7/156:55 pm
MKE
-
PDX
1 stop6h 55m
Southwest
Deal found 5/12$352
This Delta deal was found by Cheapflights users on 5/10. 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 6/66:00 am
PDX
-
MKE
1 stop7h 09m
Delta
Sat 6/203:58 pm
MKE
-
PDX
1 stop6h 19m
Delta
Deal found 5/10$355
This Delta deal was found by Cheapflights users on 5/11. 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 6/35:20 am
BOI
-
MKE
1 stop5h 00m
Delta
Wed 6/35:48 pm
MKE
-
BOI
1 stop8h 00m
Delta
Deal found 5/11$357
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/1010:59 pm
PDX
-
MKE
1 stop6h 43m
American Airlines
Tue 6/306:50 pm
MKE
-
PDX
1 stop6h 57m
American Airlines
Deal found 5/14$358
This Delta deal was found by Cheapflights users on 5/11. 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 8/2512:32 pm
RDM
-
MKE
1 stop7h 11m
Delta
Tue 9/17:15 am
MKE
-
RDM
1 stop6h 39m
Delta
Deal found 5/11$359
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1711:30 pm
PDX
-
MKE
2 stops10h 30m
Southwest
Thu 8/206:20 pm
MKE
-
PDX
1 stop7h 05m
Southwest
Deal found 5/13$360
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:20 pm
PDX
-
MKE
1 stop12h 30m
Southwest
Wed 6/107:05 pm
MKE
-
PDX
1 stop7h 00m
Southwest
Deal found 5/13$361
This Delta deal was found by Cheapflights users on 5/11. 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 8/196:20 am
RDM
-
MKE
2 stops13h 23m
Delta
Wed 8/267:30 am
MKE
-
RDM
1 stop6h 20m
Delta
Deal found 5/11$364
This American Airlines deal was found by Cheapflights users on 5/14. 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 7/110:59 pm
PDX
-
MKE
1 stop7h 03m
American Airlines
Mon 7/66:55 pm
MKE
-
PDX
1 stop7h 09m
American Airlines
Deal found 5/14$365

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 May 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(American Airlines)

One-way from

$165
(Delta)

Popular in

February

Cheapest in

January

Average price

$436
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
From Oregon to Milwaukee-Mitchell
One-way flight from Oregon to Milwaukee-Mitchell
Highest demand for flights based on searches. 7% potential increase in price ($38 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 May 15, 2026.
Use the filters below to find and compare flights from Oregon to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RedmondMilwaukee

RDM - MKE

RDMMKE

Bend/Redmond

Wed 8/19

6:20 am-9:43 pm

2 stops13h 23m

Milwaukee-Mitchell

Wed 8/26

7:30 am-11:50 am

1 stop6h 20m

$364

EugeneMilwaukee

EUG - MKE

EUGMKE

Eugene

Mon 6/1

1:45 pm-11:59 pm

1 stop8h 14m

Milwaukee-Mitchell

Tue 6/9

7:00 am-1:08 pm

1 stop8h 08m

$388

EugeneMilwaukee

EUG - MKE

EUGMKE

Eugene

Fri 6/5

2:45 pm-10:25 pm

1 stop5h 40m

Milwaukee-Mitchell

Tue 6/9

5:00 am-9:50 am

1 stop6h 50m

$388

EugeneMilwaukee

EUG - MKE

EUGMKE

Eugene

Wed 7/8

6:00 am-7:31 pm

2 stops11h 31m

Milwaukee-Mitchell

Sat 7/11

7:00 am-11:48 am

1 stop6h 48m

$388

EugeneMilwaukee

EUG - MKE

EUGMKE

Eugene

Thu 6/4

1:45 pm-11:59 pm

1 stop8h 14m

Milwaukee-Mitchell

Wed 6/10

6:02 am-1:01 pm

1 stop8h 59m

$393

MedfordMilwaukee

MFR - MKE

MFRMKE

Medford

Wed 7/22

6:01 am-8:20 pm

2 stops12h 19m

Milwaukee-Mitchell

Mon 7/27

3:59 pm-11:11 pm

2 stops9h 12m

$396

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 6/4

9:20 pm-11:50 am

1 stop12h 30m

Milwaukee-Mitchell

Tue 6/9

5:00 am-12:00 pm

2 stops9h 00m

$397

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 7/7

2:35 pm-10:15 pm

1 stop5h 40m

Milwaukee-Mitchell

Fri 7/17

5:15 pm-11:55 pm

1 stop8h 40m

$403

BoiseMilwaukee

BOI - MKE

BOIMKE

Boise Air Term. Gowen Fld

Tue 9/29

6:20 am-2:07 pm

1 stop6h 47m

Milwaukee-Mitchell

Wed 9/30

3:03 pm-10:38 pm

1 stop8h 35m

$403

MedfordMilwaukee

MFR - MKE

MFRMKE

Medford

Fri 5/29

6:15 am-9:33 pm

2 stops13h 18m

Milwaukee-Mitchell

Tue 6/2

5:01 pm-11:42 pm

2 stops8h 41m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Oregon to Milwaukee?

Booking 32 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oregon to Milwaukee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 February is currently the most expensive (average of $339). 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.

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

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 5h 40m. The distance from Oregon to Milwaukee is about 1756 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?

    $118 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $138 and $139, respectively.

  • What are the most popular routes 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 February is currently the most expensive (average of $339). 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
Port Washington
New Berlin
Oak Creek
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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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.

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 May 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$562FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$416FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$242Average$477FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$278Average$458FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$292Average$454FlexibilityNo cancel feeOn-time75%

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