Wisconsin

$63+ Cheap flights from Portland (PDX) 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Feb 26 — Mar 51
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Cheap flight deals from Portland to Wisconsin

Cheapest flights from Portland to Wisconsin
Explore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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 2/266:45 am
PDX
-
MSP
1 stop6h 20m
Southwest
Sun 3/17:50 pm
MSP
-
PDX
1 stop6h 15m
Southwest
Deal found 1/27$217
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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.
Sat 4/257:55 am
PDX
-
ORD
Nonstop4h 13m
Alaska Airlines
Fri 5/83:52 pm
ORD
-
PDX
1 stop9h 32m
Alaska Airlines
Deal found 1/26$217
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 3/1311:59 pm
PDX
-
ORD
Nonstop3h 57m
American Airlines
Fri 3/209:44 pm
ORD
-
PDX
Nonstop4h 31m
American Airlines
Deal found 1/27$219
This Orbitz deal was found by Cheapflights users on 1/24. 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.
Mon 4/139:32 pm
PDX
-
ORD
1 stop14h 49m
Multiple Airlines
Sat 4/257:21 pm
ORD
-
PDX
1 stop18h 36m
Multiple Airlines
Deal found 1/24$220
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Thu 3/1211:59 pm
PDX
-
ORD
Nonstop3h 57m
American Airlines
Thu 3/199:44 pm
ORD
-
PDX
Nonstop4h 31m
American Airlines
Deal found 1/26$221
This United Airlines deal was found by Cheapflights users on 1/25. 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.
Sat 2/141:40 pm
PDX
-
ORD
1 stop7h 46m
United Airlines
Tue 2/179:10 am
ORD
-
PDX
Nonstop4h 45m
United Airlines
Deal found 1/25$224
This Expedia deal was found by Cheapflights users on 1/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:48 am
PDX
-
MSP
1 stop10h 10m
Multiple Airlines
Sun 4/263:48 pm
MSP
-
PDX
Nonstop3h 37m
Multiple Airlines
Deal found 1/25$225
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:55 am
PDX
-
ORD
Nonstop4h 13m
Multiple Airlines
Sat 5/169:18 pm
ORD
-
PDX
1 stop13h 41m
Multiple Airlines
Deal found 1/26$225
This CheapOair deal was found by Cheapflights users on 1/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:48 am
PDX
-
MSP
1 stop25h 06m
Frontier
Sun 4/196:45 am
MSP
-
PDX
1 stop6h 18m
Frontier
Deal found 1/25$226
This CheapOair deal was found by Cheapflights users on 1/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:53 am
PDX
-
ORD
1 stop17h 57m
Frontier
Sun 4/2610:55 am
ORD
-
PDX
1 stop26h 08m
Frontier
Deal found 1/25$226
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 2/249:44 pm
PDX
-
MSP
1 stop10h 27m
American Airlines
Tue 3/36:20 pm
MSP
-
PDX
1 stop7h 57m
American Airlines
Deal found 1/27$227
This Delta deal was found by Cheapflights users on 1/26. 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 4/2212:30 am
PDX
-
ORD
1 stop6h 08m
Delta
Tue 5/57:12 pm
ORD
-
PDX
1 stop6h 41m
Delta
Deal found 1/26$227

Find flight deals from Portland to Wisconsin

Keep the following information in mind while searching for Portland to Wisconsin flight deals. Data was last updated January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Southwest)

One-way from

$63
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$341
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
From Portland to Wisconsin
One-way flight from Portland to Wisconsin
Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in January 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 January 27, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.

Fly from

Portland

Fly to

Wisconsin

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 2/27

12:40 am-10:25 am

1 stop7h 45m

Chicago O'Hare Intl

Tue 3/3

6:15 am-12:44 pm

1 stop8h 29m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 3/13

12:30 am-8:52 am

1 stop6h 22m

Chicago O'Hare Intl

Wed 3/18

1:57 pm-9:53 pm

1 stop9h 56m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/28

11:15 pm-7:43 am

1 stop6h 28m

Chicago O'Hare Intl

Wed 5/6

7:12 pm-11:53 pm

1 stop6h 41m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/21

1:53 pm-9:30 pm

1 stop5h 37m

Chicago O'Hare Intl

Mon 2/23

2:20 pm-8:55 pm

1 stop8h 35m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/10

10:30 pm-8:30 am

1 stop8h 00m

Chicago O'Hare Intl

Mon 3/16

7:10 pm-11:54 pm

1 stop6h 44m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 4/24

7:55 am-2:08 pm

Nonstop4h 13m

Chicago O'Hare Intl

Sat 5/2

2:13 pm-4:50 pm

Nonstop4h 37m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/14

1:32 pm-9:52 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 2/18

6:15 am-12:44 pm

1 stop8h 29m

$234

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 2/24

5:05 am-2:57 pm

1 stop7h 52m

Milwaukee-Mitchell

Tue 3/3

4:10 pm-9:15 pm

1 stop7h 05m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 3/13

11:15 pm-9:10 am

1 stop7h 55m

Chicago O'Hare Intl

Mon 3/16

7:10 pm-11:54 pm

1 stop6h 44m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 2/20

1:32 pm-9:52 pm

1 stop6h 20m

Chicago O'Hare Intl

Mon 2/23

2:20 pm-8:55 pm

1 stop8h 35m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 60 results
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Best time to book a flight from Portland to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Portland 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 Portland to Wisconsin

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

Currently, October is the cheapest month in which you can book a flight from Portland to Wisconsin (average of $79). Flying from Portland to Wisconsin in November is currently the most expensive (average of $281). 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 Portland to Wisconsin?

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 January 27, 2026.
See what other customers who have flown with Southwest, Delta, and United Airlines from Portland to Wisconsin have to say. 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.

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Portland to Wisconsin. 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 from for flights from Portland to Wisconsin?

    Most people fly from Portland (PDX) if they book a flight from Portland to Wisconsin. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • How long is the flight from Portland to Wisconsin?

    Airlines like Delta, United Airlines, and Alaska Airlines fly from Portland to Wisconsin in about 7h 45m. The time it takes to get you to your destination can typically vary by up to 10h 53m. The distance from Portland to Wisconsin is about 1733 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 Portland to Wisconsin one-way?

    One-way options have recently been found by users for as low as $64 on Allegiant Air. Other airlines that offer cheap prices include American Airlines from $114 and Delta from $114 one-way.

  • What are the most popular routes from Portland to Wisconsin?

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Portland to Wisconsin (average of $79). Flying from Portland to Wisconsin in November is currently the most expensive (average of $281). 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 Portland to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Portland to Wisconsin

Discover the top 7 airlines that operate flights from Portland 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$71Average$160FlexibilityNo cancel feeOn-time88%
DeltaCheapest$88Average$494FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$149Average$258FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$209Average$474FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$489FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$324Average$416FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$339Average$514FlexibilityNo cancel feeOn-time63%

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