Wisconsin

$110+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
May 8 — May 151
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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 April 8, 2026.

This CheapOair deal was found by Cheapflights users on 4/4. 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 4/2311:48 am
PDX
-
MKE
1 stop27h 46m
Frontier
Mon 4/275:05 pm
MKE
-
PDX
1 stop20h 47m
Frontier
Deal found 4/4$217
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/88:46 pm
PDX
-
MSP
2 stops10h 33m
Multiple Airlines
Mon 5/117:00 am
MSP
-
PDX
Nonstop3h 32m
Multiple Airlines
Deal found 4/3$233
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 5/2912:35 pm
PDX
-
MSP
1 stop18h 44m
Multiple Airlines
Fri 6/59:05 pm
MSP
-
PDX
Nonstop3h 38m
Multiple Airlines
Deal found 4/4$234
This CheapOair deal was found by Cheapflights users on 4/6. 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 4/3011:58 am
PDX
-
MSP
1 stop21h 04m
Frontier
Wed 5/69:39 pm
MSP
-
PDX
1 stop21h 07m
Frontier
Deal found 4/6$236
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 6/46:40 pm
PDX
-
MSP
Nonstop3h 15m
Sun Country Air
Thu 7/309:05 pm
MSP
-
PDX
Nonstop3h 38m
Sun Country Air
Deal found 4/5$237
This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Tue 6/25:46 pm
PDX
-
MSP
1 stop13h 33m
Frontier
Tue 8/410:18 am
MSP
-
PDX
1 stop8h 39m
Frontier
Deal found 4/5$238
This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Tue 6/25:46 pm
PDX
-
MSP
1 stop13h 33m
Multiple Airlines
Thu 7/99:05 pm
MSP
-
PDX
Nonstop3h 38m
Multiple Airlines
Deal found 4/5$239
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Tue 6/25:46 pm
PDX
-
MSP
1 stop13h 33m
Frontier
Fri 6/1210:15 pm
MSP
-
PDX
1 stop20h 42m
Frontier
Deal found 4/4$241
This Sun Country Air deal was found by Cheapflights users on 4/6. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:59 pm
PDX
-
MSP
Nonstop3h 15m
Sun Country Air
Mon 6/83:20 pm
MSP
-
PDX
Nonstop3h 39m
Sun Country Air
Deal found 4/6$244
This Kiwi.com deal was found by Cheapflights users on 4/3. 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.
Sat 4/2512:27 pm
PDX
-
ORD
2 stops15h 53m
Frontier
Sat 5/27:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Deal found 4/3$244
This Orbitz deal was found by Cheapflights users on 4/6. 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 5/712:35 pm
PDX
-
MSP
1 stop18h 44m
Multiple Airlines
Mon 5/117:00 am
MSP
-
PDX
Nonstop3h 32m
Multiple Airlines
Deal found 4/6$245
This Priceline deal was found by Cheapflights users on 4/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
-
MSP
1 stop10h 10m
Multiple Airlines
Sun 4/263:48 pm
MSP
-
PDX
Nonstop3h 31m
Multiple Airlines
Deal found 4/5$246

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 April 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(CheapOair)

One-way from

$110
(Trip.com)

Popular in

February

Cheapest in

January

Average price

$404

Good round-trip deal

$276 or less

Good one-way deal

$180 or less
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. 7% potential increase in price ($35 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in April 2026
Price to beat on a round-trip flight from Portland to Wisconsin.
Price to beat on a one-way flight from Portland to Wisconsin.

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 April 8, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/6

11:55 pm-6:00 am

Nonstop4h 05m

Chicago O'Hare Intl

Tue 5/12

8:00 pm-10:35 pm

Nonstop4h 35m

$251

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 4/27

12:45 pm-6:08 am

1 stop15h 23m

Chicago O'Hare Intl

Tue 4/28

5:57 pm-11:03 am

2 stops43h 06m

$263

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/6

8:50 am-6:50 pm

1 stop8h 00m

Chicago O'Hare Intl

Tue 5/12

11:55 am-9:00 pm

2 stops11h 05m

$276

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 5/9

7:10 am-10:20 pm

2 stops13h 10m

Chicago O'Hare Intl

Tue 5/12

4:50 pm-11:10 pm

1 stop8h 20m

$276

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/28

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Thu 5/7

12:44 pm-3:13 pm

Nonstop4h 29m

$289

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 5/7

11:55 pm-6:00 am

Nonstop4h 05m

Chicago O'Hare Intl

Tue 5/12

8:00 pm-10:35 pm

Nonstop4h 35m

$289

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/13

11:12 pm-8:45 am

1 stop7h 33m

Chicago O'Hare Intl

Wed 5/27

12:47 pm-5:11 pm

1 stop6h 24m

$298

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 5/23

4:15 pm-12:44 am

1 stop6h 29m

Chicago O'Hare Intl

Tue 5/26

7:05 am-9:39 am

Nonstop4h 34m

$315

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/23

5:35 pm-11:41 pm

Nonstop4h 06m

Chicago O'Hare Intl

Sun 9/27

7:00 am-9:28 am

Nonstop4h 28m

$316

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/30

11:55 pm-6:00 am

Nonstop4h 05m

Chicago O'Hare Intl

Sat 5/2

12:05 pm-6:46 pm

1 stop8h 41m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 60 resultsSorted by cheapest first
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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 March is currently the most expensive (average of $308). 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 April 8, 2026.
See what other customers who have flown with Southwest,Delta, andUnited 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.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 United Airlines, Frontier, and Southwest fly from Portland to Wisconsin in about 4h 05m. The time it takes to get you to your destination can typically vary by up to 11h 18m. 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 United Airlines from $118 and American Airlines from $125 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 March is currently the most expensive (average of $308). 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 April 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$71Average$156FlexibilityNo cancel feeOn-time88%
DeltaCheapest$88Average$483FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$149Average$258FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$209Average$468FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$462FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$307Average$422FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$322Average$499FlexibilityNo cancel feeOn-time63%

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