Oregon

$196+ Cheap flights from Wisconsin to Oregon

MKE — PDX
Dec 13 — Dec 201
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1. Tell us where you want to go

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Cheap flight deals from Wisconsin to Oregon

Cheapest flights from Wisconsin to Oregon

Thu 12/105:51 am -
1 stop8h 46m
Tue 12/2911:31 pm -
1 stop6h 41m
Deal found 11/9$390
Fri 12/49:54 am -
1 stop7h 25m
Thu 12/102:26 pm -
1 stop6h 33m
Deal found 11/10$399
Mon 12/75:40 pm -
1 stop8h 09m
Mon 12/1411:39 pm -
1 stop9h 16m
Deal found 11/9$399
Tue 12/14:25 pm -
1 stop6h 29m
Sat 12/55:32 pm -
1 stop19h 55m
Deal found 11/8$399
Thu 12/105:00 am -
2 stops11h 38m
Sun 12/132:26 pm -
1 stop6h 34m
Deal found 11/10$404
Wed 12/212:15 pm -
1 stop8h 28m
Wed 12/95:00 am -
2 stops8h 03m
Deal found 11/9$404
Thu 12/1012:41 pm -
2 stops11h 25m
Sun 12/139:57 am -
2 stops8h 59m
Deal found 11/10$409
Thu 12/32:54 pm -
1 stop10h 31m
Sat 12/51:30 pm -
1 stop8h 38m
Deal found 11/12$409
Tue 12/83:50 pm -
1 stop6h 34m
Sat 12/1211:17 pm -
1 stop7h 30m
Deal found 11/10$409
Thu 12/312:37 pm -
2 stops9h 37m
Sun 12/67:10 am -
2 stops12h 29m
Deal found 11/8$409
Thu 12/39:54 am -
2 stops10h 29m
Mon 12/72:26 pm -
1 stop6h 33m
Deal found 11/8$412
Mon 12/74:45 pm -
1 stop7h 05m
Sat 12/1212:35 pm -
1 stop6h 40m
Deal found 11/9$414

Find flight deals from Wisconsin to Oregon

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$381
(Delta)

One-way from

$196
(Kiwi.com)

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 Wisconsin to Oregon
One-way flight from Wisconsin 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 Wisconsin 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

Thu 12/3

9:15 am-6:07 pm

2 stops10h 52m

Portland

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$230

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

MilwaukeeRedmond

MKE Milwaukee-Mitchell - RDM Bend/Redmond

MKERDM

Milwaukee-Mitchell

Fri 1/15

12:45 pm-9:11 pm

2 stops10h 26m

Bend/Redmond

Wed 12/31

12:00 am-2:00 am

Nonstop0h 00m

$240

MilwaukeeRedmond

MKE Milwaukee-Mitchell - RDM Bend/Redmond

MKERDM

Milwaukee-Mitchell

Thu 1/14

10:35 am-6:23 pm

2 stops9h 48m

Bend/Redmond

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

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Wisconsin to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Wisconsin with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Oregon

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

Currently, June is the cheapest month in which you can book a flight from Wisconsin to Oregon (average of $365). Flying from Wisconsin to Oregon in October is currently the most expensive (average of $506). 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 Wisconsin to Oregon?

Airfare is below average for this route at the moment.
Wisconsin 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 1-Dec 5).

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

The best time to book flights from Wisconsin to Oregon is 77 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Reviews of airlines servicing Oregon

Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Wisconsin to Oregon to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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

  • How long is the flight from Wisconsin to Oregon?

    There are many flights that can get you from Wisconsin to Oregon in 7h. Fly via Delta, United Airlines, or American Airlines to get the fastest option. Wisconsin and Oregon are separated by a distance of 1639 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $70. Delta flights start at $124 while deals on United Airlines start at $142 one-way.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Wisconsin to Oregon (average of $365). Flying from Wisconsin to Oregon in October is currently the most expensive (average of $506). 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 Wisconsin to Oregon

Top 6 airlines flying from Wisconsin to Oregon

AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$189Average$299FlexibilityNo cancel feeOn-time88%
DeltaCheapest$239Average$463FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$241Average$444FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$263Average$489FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$280Average$469FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$336Average$496FlexibilityNo cancel feeOn-time63%

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