$85 Find Cheap Flights from Portland to Wisconsin - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Wisconsin departing on 8/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Wisconsin

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Wisconsin, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Wisconsin, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Portland to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$329
Madison
Madison1 stop$305
Appleton
Appleton1 stop$388
Green Bay
Green Bay1 stop$309
Wausau
Wausau1 stop$319
Minneapolis
Minneapolisnonstop$197
Duluth
Duluth2 stops$314
Chicago
Chicagononstop$307
Milwaukee
Milwaukee1 stop$329
Madison
Madison1 stop$305
Appleton
Appleton1 stop$388
Green Bay
Green Bay1 stop$309
Wausau
Wausau1 stop$319
Minneapolis
Minneapolisnonstop$197
Duluth
Duluth2 stops$314
Chicago
Chicagononstop$307

Book Cheap Portland to Wisconsin Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Wisconsin that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Wisconsin

Fri, Jul 10 - Sun, Jul 12
Sun Country Air Logo
11:16 am - 1:25 pm
PWM
-
MSP
3h 09mnonstop
Sun Country Air Logo
7:55 am - 11:37 am
MSP
-
PWM
2h 42mnonstop
$197Sun Country Air
Fri, Jul 10 - Mon, Jul 13
Sun Country Air Logo
11:16 am - 1:25 pm
PWM
-
MSP
3h 09mnonstop
Sun Country Air Logo
7:55 am - 11:37 am
MSP
-
PWM
2h 42mnonstop
$207Sun Country Air
Thu, Jul 30 - Sat, Aug 8
American Airlines Logo
1:25 pm - 7:39 pm
PWM
-
MSN
7h 14m
1 stop
American Airlines Logo
1:25 pm - 8:10 pm
MSN
-
PWM
5h 45m
1 stop
$305American Airlines
Wed, Jul 22 - Sat, Jul 25
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
6:08 pm - 9:41 pm
ORD
-
PWM
2h 33mnonstop
$307United Airlines
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
6:09 pm - 12:16 am
PWM
-
GRB
7h 07m
1 stop
American Airlines Logo
5:55 am - 11:38 am
GRB
-
PWM
4h 43m
1 stop
$309American Airlines
Mon, Oct 26 - Sat, Oct 31
Delta Logo
3:00 pm - 10:48 pm
PWM
-
DLH
8h 48m
2 stops
Delta Logo
5:10 am - 10:55 am
DLH
-
PWM
4h 45m
1 stop
$314Delta
Thu, Oct 22 - Sat, Oct 24
Delta Logo
12:50 pm - 6:40 pm
PWM
-
ORD
6h 50m
1 stop
Delta Logo
6:00 am - 4:10 pm
ORD
-
PWM
9h 10m
2 stops
$315Delta
Wed, Jul 22 - Sat, Jul 25
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
3:57 pm - 11:30 pm
ORD
-
PWM
6h 33m
1 stop
$317United Airlines
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
3:25 pm - 11:05 pm
PWM
-
MKE
8h 40m
2 stops
Southwest Logo
5:10 am - 12:05 pm
MKE
-
PWM
5h 55m
1 stop
$346Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
3:25 pm - 10:50 pm
PWM
-
MKE
8h 25m
2 stops
Southwest Logo
4:50 pm - 12:05 am
MKE
-
PWM
6h 15m
2 stops
$351Southwest
Booking Insights

KAYAK's insights & trends for Portland to Wisconsin flights

Get data-powered insights and trends into flights from Portland to Wisconsin to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Portland, Maine to Wisconsin?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland, Maine to Wisconsin departing in October.

What is the cheapest month to fly from Portland to Wisconsin?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Wisconsin, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Wisconsin is July, when tickets cost $177 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $329 and $314 respectively.

Good to know

Low seasonFebruary
Cheapest flight$85
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from Portland to Chicago O'Hare Airport

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from Portland to Wisconsin?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Wisconsin.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Wisconsin?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to Wisconsin is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to Wisconsin?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Portland to Wisconsin with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Wisconsin?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Portland to Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Wisconsin

  • Looking for a cheap flight? 25% of our users found tickets from Portland to the following destinations at these prices or less: Minneapolis $201 one-way - $328 round-trip; Chicago $229 one-way - $399 round-trip

Reviews of the top 4 airlines serving from Portland to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Portland to Wisconsin. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Wisconsin? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible I am at almost 2,000,000 miles on United. This was probably the worst flight ever. An hour and a half before takeoff I get a message that they’re changing the plane and I no longer have a seat in Polaris business Supposedly, there was a problem with the plane, but then there was no other plane Finally, they decided to bring a plane from Newark to Washington Dulles Of course the original flight was at 10:45 PM so by the time the plane got there it was 12:30 AM. It had not been cleaned. It had not been catered. They don’t really have people available to do those things when it’s not pre-programmed at 1 o’clock in the morning. The crew had to be changed And the new plane held 28 fewer people than the scheduled plane There is no way you can hate United Airlines enough The people at the gate were actually just fine, but it was management who was completely useless And did they send extra help to the people at the gate? Did they send supervisors? Of course not. Just don’t take United find somebody else or buy a boat

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Checking bag at terminal was horrible. No agents to check us in and only 1 kiosk working. Boarding went ok. Crew onboard was very scattered rained. Missed our row while serving and then didn’t see them hardly again.

Crew was amazing, takeoff wonderful. The bathroom was disgusting from before takeoff the odor made the flight uncomfortable as you could smell the bathroom from the center of the plane where we were sitting. Smelled like raw sewage. My daughter was throwing up as we landed due to the smell and horrible turbulence as we approached Newark.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

Maybe focus more on delivering a good product vs selling me a damn credit card

American Airlines is a great dependable airline, on time arrival and departure with polite crew and staff.

I think since I am an AA Advantage member, my checked bags should have been free, but I paid for all 4 of us.

This flight moved Gates several times in a short time period, from B to C, which required a substantial walk or rail ride. Then the flight was delayed more than 2 hours and the food was subpar compared to other flights.

Flight was delayed multiple times without giving any particular reason and the only thing that was communicated was that 'Aircraft is getting ready'. I was stuck at SFO airport for 15 hours and finally took Southwest Airlines flight back home to Dallas.

Hydraulic leak caused the flight to be cancelled. Auto system scheduled us on a 3 am flight. Wevhsedvrebook on the app and hit schedules later in the afternoon. Our luggage per gate and ticket agent would be rescanned and put in our new flight. Did not happen. Our luggage stayed in hsv. Baggage claim in wash dc unable to help. We filed a claim. Several emails about our luggage were in conflict with one another. Called as baggage and was on hold 30 minutes. Oscar said one of 2 was out fir delivery then cancelled. About 45 minutes later both pieces were delivered. Their system is suspect

I was not clear if food was offered or not.

Flight cancelled. Twice. And no communication. No gate agent. Went past boarding time and had to go and see email from AA. Airport communication was bad

Everything you need to know for your flight from Portland to Wisconsin

Information on your arrival and departure airports