Oregon

$200+ Cheap flights from Milwaukee (MKE) to Oregon

MKE — PDX
Dec 11 — Dec 181
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Cheap flight deals from Milwaukee to Oregon

Cheapest flights from Milwaukee to Oregon

Tue 12/224:27 pm -
1 stop8h 32m
Tue 12/298:21 am -
1 stop13h 38m
Deal found 11/8$399
Wed 12/212:15 pm -
1 stop8h 28m
Wed 12/95:00 am -
2 stops8h 03m
Deal found 11/9$404
Tue 12/83:50 pm -
1 stop6h 34m
Sat 12/1211:17 pm -
1 stop7h 30m
Deal found 11/10$409
Mon 12/74:45 pm -
1 stop7h 05m
Sat 12/1212:35 pm -
1 stop6h 40m
Deal found 11/9$414
Thu 12/37:20 am -
1 stop6h 35m
Wed 12/91:41 pm -
1 stop6h 11m
Deal found 11/10$416
Sat 12/194:27 pm -
1 stop8h 32m
Fri 12/256:05 am -
1 stop7h 28m
Deal found 11/8$424
Tue 12/1512:45 pm -
2 stops10h 45m
Sat 12/198:05 pm -
1 stop13h 10m
Deal found 11/7$425
Mon 12/74:25 pm -
1 stop7h 27m
Tue 12/87:30 am -
1 stop5h 57m
Deal found 11/10$429
Wed 12/26:20 am -
2 stops8h 50m
Wed 12/910:15 am -
2 stops11h 00m
Deal found 11/9$434
Fri 12/256:00 am -
1 stop9h 24m
Thu 12/316:05 am -
1 stop7h 24m
Deal found 11/8$439
Fri 12/44:25 pm -
1 stop9h 30m
Wed 12/96:26 am -
1 stop7h 01m
Deal found 11/10$444
Thu 12/33:59 pm -
1 stop7h 38m
Wed 12/95:00 am -
1 stop6h 24m
Deal found 11/9$459

Find flight deals from Milwaukee to Oregon

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$391
(Delta)

One-way from

$200
(Priceline)

Popular in

November

Cheapest in

January

Average price

$649
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
From Milwaukee-Mitchell to Oregon
One-way flight from Milwaukee-Mitchell to Oregon
Highest demand for flights based on searches. 10% potential increase in price ($52 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeePortland

MKE Milwaukee-Mitchell - PDX Portland

MKEPDX

Milwaukee-Mitchell

Tue 12/1

4:25 pm-9:52 pm

1 stop7h 27m

Portland

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$205

MilwaukeePortland

MKE Milwaukee-Mitchell - PDX Portland

MKEPDX

Milwaukee-Mitchell

Mon 12/14

5:45 am-10:40 am

1 stop6h 55m

Portland

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$215

MilwaukeePortland

MKE Milwaukee-Mitchell - PDX Portland

MKEPDX

Milwaukee-Mitchell

Thu 1/14

12:45 pm-6:59 pm

1 stop8h 14m

Portland

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$225

MilwaukeePortland

MKE Milwaukee-Mitchell - PDX Portland

MKEPDX

Milwaukee-Mitchell

Fri 1/15

6:30 am-11:45 am

1 stop7h 15m

Portland

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$240

MilwaukeePortland

MKE Milwaukee-Mitchell - PDX Portland

MKEPDX

Milwaukee-Mitchell

Fri 1/15

2:40 pm-10:45 pm

2 stops10h 05m

Portland

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$245

MilwaukeeMedford

MKE Milwaukee-Mitchell - MFR Medford

MKEMFR

Milwaukee-Mitchell

Thu 12/3

7:20 am-11:51 am

1 stop6h 31m

Medford

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$247

MilwaukeeMedford

MKE Milwaukee-Mitchell - MFR Medford

MKEMFR

Milwaukee-Mitchell

Thu 12/3

4:25 pm-11:59 pm

1 stop9h 34m

Medford

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$247

MilwaukeeMedford

MKE Milwaukee-Mitchell - MFR Medford

MKEMFR

Milwaukee-Mitchell

Wed 12/2

4:25 pm-11:59 pm

1 stop9h 34m

Medford

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$247

MilwaukeeMedford

MKE Milwaukee-Mitchell - MFR Medford

MKEMFR

Milwaukee-Mitchell

Tue 12/1

4:25 pm-11:59 pm

1 stop9h 34m

Medford

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$247

MilwaukeeRedmond

MKE Milwaukee-Mitchell - RDM Bend/Redmond

MKERDM

Milwaukee-Mitchell

Tue 12/22

4:27 pm-9:19 pm

1 stop6h 52m

Bend/Redmond

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 59 resultsSorted by cheapest first
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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

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, March is the cheapest month in which you can book a flight from Milwaukee to Oregon (average of $379). Flying from Milwaukee to Oregon in July is currently the most expensive (average of $565). 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 Milwaukee to Oregon?

Airfare is below average for this route at the moment.
Milwaukee to Oregon flights typically cost between $468 and $810 in December.
The cheapest round-trip price found within the last 5 days was $399 on Alaska Airlines (Dec 22-Dec 29).

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

The price you pay for your flight from Milwaukee to Oregon may vary depending on when you book. For the best chance of a lower fare, look to book 19 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing Oregon

Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta 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.

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

  • 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, Southwest, and United Airlines fly from Milwaukee to Oregon in about 6h 24m. The time it takes to get you to your destination can typically vary by up to 1h 03m. 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 Delta, which is currently one of the cheapest options available, starting at $124. United Airlines flights start at $142 while deals on Alaska Airlines start at $158 one-way.

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

  • 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, March is the cheapest month in which you can book a flight from Milwaukee to Oregon (average of $379). Flying from Milwaukee to Oregon in July is currently the most expensive (average of $565). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Milwaukee to Oregon

Top 5 airlines flying from Milwaukee to Oregon

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$239Average$455FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$241Average$444FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$263Average$447FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$316Average$417FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$336Average$496FlexibilityNo cancel feeOn-time63%

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