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Wisconsin

$53+ Cheap flights from Oregon to Wisconsin

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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Oregon to Wisconsin

Keep the following information in mind while searching for Oregon to Wisconsin flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$144
(Kiwi.com)

One-way from

$53
(Trip.com)

Popular in

March

Cheapest in

April

Average price

$494

Good round-trip deal

$83 or less
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
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From Oregon to Wisconsin
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One-way flight from Oregon to Wisconsin
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Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Oregon to Wisconsin.
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Find flight deals from Oregon to Wisconsin

Cheapest flights from Oregon to Wisconsin
Explore the most affordable flight options available from Oregon to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:33 pmBOI - MSP
1 stop19h 47mFrontier
Sat 11/1510:15 amMSP - BOI
1 stop26h 28mFrontier
Deal found 10/28$139
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:33 pmBOI - MSP
1 stop10h 41mFrontier
Sun 11/166:00 amMSP - BOI
1 stop6h 43mFrontier
Deal found 10/28$143
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/912:33 pmBOI - MSP
1 stop19h 47mFrontier
Wed 11/128:51 amMSP - BOI
1 stop27h 52mFrontier
Deal found 10/28$152
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:52 pmPDX - MKE
1 stop28h 27mFrontier
Mon 11/178:04 pmMKE - PDX
1 stop17h 52mFrontier
Deal found 10/29$159
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 12/37:16 amPDX - MSP
Nonstop3h 27mAlaska Airlines
Wed 12/171:39 pmMSP - PDX
Nonstop3h 49mAlaska Airlines
Deal found 10/29$177
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:12 pmPDX - MSP
Nonstop3h 18mSun Country Air
Sun 11/233:48 pmMSP - PDX
Nonstop3h 48mSun Country Air
Deal found 10/30$178
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/712:51 pmPDX - MSP
1 stop9h 11mFrontier
Sun 12/147:00 amMSP - PDX
1 stop6h 56mFrontier
Deal found 10/29$179
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:38 pmBOI - MSP
1 stop10h 24mFrontier
Thu 1/16:45 amMSP - BOI
1 stop5h 58mFrontier
Deal found 10/30$179
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/2512:38 pmBOI - MSP
1 stop10h 24mFrontier
Sat 1/36:45 amMSP - BOI
1 stop6h 14mFrontier
Deal found 10/29$181
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:52 pmPDX - MSP
1 stop18h 28mMultiple Airlines
Mon 11/173:42 pmMSP - PDX
Nonstop3h 48mMultiple Airlines
Deal found 10/30$182
This Orbitz deal was found by Cheapflights users on 10/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:51 pmPDX - MSP
1 stop9h 11mMultiple Airlines
Tue 1/61:32 pmMSP - PDX
Nonstop3h 54mMultiple Airlines
Deal found 10/30$184
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/286:36 pmPDX - MSP
Nonstop3h 18mMultiple Airlines
Fri 12/57:00 amMSP - PDX
1 stop6h 56mMultiple Airlines
Deal found 10/29$185

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Wisconsin 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 October 30, 2025.
Use the filters below to find and compare flights from Oregon to Wisconsin that are best for you.

Fly from

Oregon

Fly to

Wisconsin

Route

Depart

Return

Price

PortlandMinneapolis

PDX - MSP

PDXMSP

Portland

Wed 12/17

7:16 am-12:43 pm

Nonstop3h 27m

Minneapolis St Paul

Thu 12/25

1:32 pm-3:26 pm

Nonstop3h 54m

$223

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/10

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Mon 12/15

7:37 pm-10:15 pm

Nonstop4h 38m

$227

PortlandMinneapolis

PDX - MSP

PDXMSP

Portland

Sat 12/20

7:08 pm-12:30 am

Nonstop3h 22m

Minneapolis St Paul

Wed 12/24

3:36 pm-5:26 pm

Nonstop3h 50m

$228

PortlandMinneapolis

PDX - MSP

PDXMSP

Portland

Tue 3/10

6:00 am-1:23 pm

1 stop5h 23m

Minneapolis St Paul

Wed 3/11

8:00 am-12:36 pm

1 stop6h 36m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 12/15

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

Tue 1/13

6:12 am-12:46 pm

1 stop8h 34m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 12/9

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

Tue 12/16

6:00 am-12:54 pm

1 stop8h 54m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 11/27

7:00 am-1:02 pm

Nonstop4h 02m

Chicago O'Hare Intl

Thu 12/4

7:37 pm-10:15 pm

Nonstop4h 38m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 12/12

12:32 am-10:33 am

1 stop8h 01m

Chicago O'Hare Intl

Tue 12/16

7:20 am-12:40 pm

1 stop7h 20m

$237

PortlandMinneapolis

PDX - MSP

PDXMSP

Portland

Thu 12/11

12:32 am-5:49 am

Nonstop3h 17m

Minneapolis St Paul

Sun 12/14

11:00 am-12:54 pm

Nonstop3h 54m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 12/21

11:00 pm-5:02 am

Nonstop4h 02m

Chicago O'Hare Intl

Sun 1/11

3:49 pm-10:45 pm

1 stop8h 56m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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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
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 Wisconsin

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

Currently, August is the cheapest month in which you can book a flight from Oregon to Wisconsin (average of $82). Flying from Oregon to Wisconsin in January is currently the most expensive (average of $258). 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.

What is the cheapest time of day to fly from OR to WI?

Find hourly flight availability from Oregon to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s typically best to fly out from Oregon to Wisconsin in the afternoon. Doing so could potentially save you 39% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Oregon to Wisconsin?

Use this chart to determine the cheapest time to fly round-trip from Oregon to Wisconsin. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oregon to Wisconsin flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated October 30, 2025.
Read through reviews of airlines operating flights from Oregon to Wisconsin, such as Alaska Airlines, Southwest, and Delta. 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.
Alaska Airlines
8.0
Very good
11,217 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,217 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,243 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,998 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,998 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,035 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oregon to Wisconsin?

    Departing from Oregon to Wisconsin will take you 3h 22m. Airlines will cover a distance of 1422 mi. Most flights are nonstop.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $88. Sun Country Air flights start at $89 while deals on Alaska Airlines start at $114 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, August is the cheapest month in which you can book a flight from Oregon to Wisconsin (average of $82). Flying from Oregon to Wisconsin in January is currently the most expensive (average of $258). 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.

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Alternative routes for Oregon to Wisconsin

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Top 7 airlines flying from Oregon to Wisconsin

Discover the top 7 airlines that operate flights from Oregon to Wisconsin. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$89Average$170FlexibilityNo cancel feeOn-time88%
FrontierCheapest$128Average$259FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$579FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$242Average$475FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$258Average$560FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$278Average$505FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$283Average$522FlexibilityNo cancel feeOn-time71%

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