Wisconsin

$200+ Cheap flights from Oregon to Wisconsin

PDX — MKE
Dec 14 — Dec 211
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Find cheap flights from Oregon to Wisconsin with Cheapflights

1. Tell us where you want to go

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Cheap flight deals from Oregon to Wisconsin

Cheapest flights from Oregon to Wisconsin

Wed 12/3011:40 pm -
1 stop8h 23m
Wed 1/63:58 pm -
1 stop7h 34m
Deal found 11/10$391
Wed 12/3011:40 pm -
1 stop8h 23m
Tue 1/59:20 am -
2 stops14h 12m
Deal found 11/10$396
Thu 12/1011:17 pm -
1 stop7h 58m
Mon 12/146:32 am -
1 stop6h 16m
Deal found 11/10$399
Sat 12/121:30 pm -
1 stop7h 49m
Thu 12/174:16 pm -
1 stop9h 53m
Deal found 11/10$400
Wed 12/21:06 pm -
1 stop6h 04m
Sat 12/53:59 pm -
1 stop7h 45m
Deal found 11/12$401
Thu 12/310:43 am -
1 stop6h 22m
Mon 12/71:15 pm -
2 stops11h 30m
Deal found 11/10$404
Thu 12/102:26 pm -
1 stop5h 57m
Sun 12/135:00 am -
2 stops10h 16m
Deal found 11/10$404
Sat 12/55:23 am -
1 stop8h 04m
Tue 12/84:25 pm -
1 stop6h 29m
Deal found 11/10$409
Wed 12/95:00 am -
1 stop10h 00m
Sun 12/132:54 pm -
1 stop10h 31m
Deal found 11/13$409
Wed 12/211:59 am -
1 stop7h 58m
Wed 12/96:00 am -
1 stop8h 48m
Deal found 11/10$409
Thu 12/105:15 am -
1 stop6h 36m
Sun 12/137:15 am -
1 stop8h 20m
Deal found 11/13$419
Thu 12/36:30 am -
1 stop8h 45m
Tue 12/84:45 pm -
1 stop7h 05m
Deal found 11/10$429

Find flight deals from Oregon to Wisconsin

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$391
(United Airlines)

One-way from

$200
(Delta)

Popular in

December

Cheapest in

January

Average price

$493
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 Wisconsin
One-way flight from Oregon to Wisconsin
High demand for flights, 7% potential price rise
Cheapest flight prices on average. 1% potential price decrease ($8 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 Oregon to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

EugeneMilwaukee

EUG Eugene - MKE Milwaukee-Mitchell

EUGMKE

Eugene

Wed 1/6

5:10 am-2:08 pm

1 stop6h 58m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$201

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Wed 1/6

6:20 am-3:05 pm

1 stop6h 45m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$205

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Sat 12/19

8:05 pm-11:15 am

1 stop13h 10m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$210

EugeneMilwaukee

EUG Eugene - MKE Milwaukee-Mitchell

EUGMKE

Eugene

Thu 12/17

6:09 am-6:02 pm

2 stops9h 53m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$216

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Sat 2/13

5:05 am-7:05 pm

2 stops12h 00m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$220

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Mon 1/18

7:10 am-4:46 pm

1 stop7h 36m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$225

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Tue 12/1

11:25 am-10:45 pm

1 stop9h 20m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$225

RedmondMilwaukee

RDM Bend/Redmond - MKE Milwaukee-Mitchell

RDMMKE

Bend/Redmond

Sat 1/23

12:32 pm-9:33 pm

1 stop7h 01m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$230

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Mon 12/21

2:00 pm-1:25 am

2 stops9h 25m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$230

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Mon 1/18

2:00 pm-12:50 am

2 stops8h 50m

Milwaukee-Mitchell

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

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

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

Cheapflights Insights

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

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

Currently, January is the cheapest month in which you can book a flight from Oregon to Wisconsin (average of $334). Flying from Oregon to Wisconsin in December is currently the most expensive (average of $568). 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 Wisconsin?

Airfare is below average for this route at the moment.
Oregon to Wisconsin flights typically cost between $425 and $601 in January.
The cheapest round-trip price found within the last 5 days was $409 on United Airlines (Jan 30-Feb 3).

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

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oregon to Wisconsin. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Wisconsin

Read through reviews of airlines operating flights from Oregon to Wisconsin, such as Southwest,Alaska Airlines, andDelta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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 Oregon to Wisconsin?

    Departing from Oregon to Wisconsin will take you 6h. Airlines will cover a distance of 1756 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 Oregon to Wisconsin one-way?

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $113. United Airlines flights start at $118 while deals on American Airlines start at $138 one-way.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Oregon to Wisconsin (average of $334). Flying from Oregon to Wisconsin in December is currently the most expensive (average of $568). 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

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Alternative routes for Oregon to Wisconsin

Top 6 airlines flying from Oregon to Wisconsin

AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$81Average$272FlexibilityNo cancel feeOn-time88%
DeltaCheapest$208Average$494FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$573FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$510FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$308Average$664FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$336Average$527FlexibilityNo cancel feeOn-time63%

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