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Find cheap flights from Portland to Wisconsin from $40

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 6/5. 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
0 bags
Sat 6/29
Sat 7/6

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Best Wisconsin Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Milwaukee
Milwaukee1 stop$174
Madison
Madison1 stop$182
Appleton
Appletonnonstop$141
Green Bay
Green Bay1 stop$269
Wausau
Wausau2 stops$473
La Crosse
La Crosse1 stop$720
Rhinelander
Rhinelander2 stops$658
Minneapolis
Minneapolis1 stop$126
Chicago
Chicagononstop$84
Duluth
Duluth1 stop$241

Good to know

Low season

March

High season

August

Cheapest flight

$40
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 4% 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 to Wisconsin from Portland 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 to Wisconsin with an airline and back to Portland 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 to Wisconsin from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $154 one-way - $266 round-trip; Chicago $168 one-way - $335 round-trip
  • Morning departure is around 18% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Portland to Wisconsin

 
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.
8.0
DeltaOverall score based on 10457 reviews
7.9Comfort
8.2Boarding
7.4Food
8.6Crew
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

The Wi-Fi was unavailable on this flight for some reason.

On time take off…US cabins look tired and need of refresh!

Fantastic. Smooth boarding with an infant. Never experienced it with any other carriers.

This was a Lufthansa flight, not United. The CSA at the counter, Ashley, was not only incompetent, but quite rude. Me and two other PAX waited over 7 minutes standing in front of her and another CSA and they ignored us. We joked that we must have accidently taken invisibility pills. She could have at least said "I'll be with you in a moment, I'm currently....". I could go on about how rude she and the other CSAs were (whispering, not communicating with me, blaming the situation on others, etc.). She would not work for me. Then, she gave me literally the worst seat on the plane. the worst. My seat kept getting bumped (rammed twice by the crew with their carts and about every 5 minutes by someone using the bathroom), listening to the bathroom all night, crowded seat, etc.

My seat was broken. WiFi didn’t work. Gate crew at HOU were rude and condescending. Treated all the passengers badly. Bad experience, United.

First flight of the day… MINIMUM FUEL! 15 minute landing delay at HOU due to fog turned into a 2+ hour delay! Rather than circle, they had to divert to another city to refuel! Sat on tarmac at Austin to refuel. We ALL missed our connections! The crew, including pilots, were clueless. Crew was really a mess. At HOU, Untied employees were exceedingly rude to all. It was pitiful.

An hour and a half late is UNACCEPTABLE. The negative impact to our family is unconscionable. And for the price we were forced to pay...

28 hour delay at Fort Worth/Dallas airport, part due to weather which was unavoidable, but various other reasons - no pilot, no fa, mechanical problem, plane too small, too big, crew out of flying time, seat configuration problems.... endless and hourly updates with a different excuse. Finally told us about 3.00 am, that the flight was delayed to hours later.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Flight was 1/2 hour delayed leaving Phoenix. Otherwise it was an average flight. Flight crew on this trip was very nice.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

Was lucky to have a employee at the AA checkin counter that had compassion and understood they ordeal that we went through with our original flight being diverted, needing to stay in the aircraft and then flying to the original destination; adding hours to the trip and forcing us to miss our connection and our rebooked connection. She was able to get up on standby on the highest priority on the next flight to the closest airport we need to be at and it all worked out despite being many hours late.

Delayed so that missed connecting flight. Connecting flight was also delayed on the tarmac but they closed the gate before the rescheduled time.

I was seated next to someone who was, to be polite, not a small person. I had to press myself against the wall as I had no personal space. Aside from that the crew was wonderful and they got me home safely, which is the most important part of my journey. I am very appreciative to your air crews for the job they have, which isn't easy, and appreciative of the fact that they are professional and courteous. The employees I encountered on my journey, with the few exceptions I mentioned in a previous review, are a credit to Air Canada.

Air Canada had a lot of delays on our flight going back to Seattle. So much inconvenience for a long trip.

Moderate size plane, not completely full, easy boarding, some rows with just 2 seats so a couple can have a row to themselves

The Carry-on luggage that approved by TSA and all other airlines,- always an issue with Air Canada. This is inappropriate as my carry on suitcase meets the requirements however it always asked to check in on AC flight on the gate. Yes I have it for free, but it takes extra time to pick up on the carousel. Apparently it fit the overhead space, so why AC has this issue all the time?

The terminal this flight boarded from was so far away, poorly temperature controlled, and generally uncomfortable. The plane was small but the flight was short, so it wasn't so bad.

Seriously need to improve the time schedule and the plans

Great TV, easy boarding, wonderful ground crew and flight crew.

Pretty good service and US Migratory officers providing services in Canada was awesome, because the arrival was quick and smooth

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Rouge needs to offer seats with better pitch in economy. Many sick people on a full flight.

Book cheap flights from Portland to Wisconsin

Recent round-trip flight deals

6/12Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
6/19Wed
nonstopSpirit Airlines
4h 27mORD-PDX
$84
8/21Wed
nonstopSpirit Airlines
3h 50mPDX-ORD
8/28Wed
nonstopSpirit Airlines
4h 30mORD-PDX
$86
8/20Tue
nonstopAmerican Airlines
4h 02mPDX-ORD
8/23Fri
nonstopAmerican Airlines
4h 31mORD-PDX
$189
7/9Tue
nonstopAlaska Airlines
4h 04mPDX-ORD
7/12Fri
1 stopAlaska Airlines
7h 21mORD-PDX
$213
8/19Mon
1 stopAmerican Airlines
9h 03mPDX-ATW
8/24Sat
1 stopAmerican Airlines
9h 01mATW-PDX
$224
7/4Thu
nonstopAlaska Airlines
4h 04mPDX-ORD
7/9Tue
nonstopAlaska Airlines
4h 20mORD-PDX
$228
8/8Thu
1 stopDelta
7h 38mPDX-DLH
8/21Wed
2 stopsDelta
10h 27mDLH-PDX
$241
8/9Fri
2 stopsDelta
11h 31mPDX-DLH
8/21Wed
2 stopsDelta
7h 55mDLH-PDX
$246
7/3Wed
nonstopUnited Airlines
3h 58mPDX-ORD
7/9Tue
1 stopUnited Airlines
6h 18mORD-PDX
$250
8/17Sat
1 stopUnited Airlines
7h 53mPDX-ATW
8/21Wed
1 stopUnited Airlines
8h 33mATW-PDX
$306

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Recent one-way flight deals

6/5Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
$40
8/21Wed
nonstopSpirit Airlines
3h 50mPDX-ORD
$48
7/4Thu
nonstopAlaska Airlines
4h 04mPDX-ORD
$90
6/28Fri
nonstopUnited Airlines
3h 58mPDX-ORD
$104
8/1Thu
1 stopDelta
6h 15mPDX-ORD
$109
7/15Mon
nonstopAlaska Airlines
4h 04mPDX-ORD
$114
7/18Thu
nonstopUnited Airlines
3h 58mPDX-ORD
$115
9/30Mon
1 stopAmerican Airlines
10h 13mPDX-MSN
$121
7/19Fri
1 stopDelta
7h 39mPDX-ORD
$124
10/12Sat
1 stopAmerican Airlines
7h 36mPDX-MSP
$158

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Last minute flights from Portland to Wisconsin

Last minute flight, train and bus deals

6/1Sat
nonstopSpirit Airlines
3h 50mPDX-ORD
6/5Wed
nonstopSpirit Airlines
4h 27mORD-PDX
$125
6/4Tue
multi-stop
17h 59mPDX-ORD
6/19Wed
nonstop
4h 27mORD-PDX
$141
6/4Tue
multi-stopFrontier
19h 10mPDX-MSP
6/12Wed
multi-stopFrontier
26h 33mMSP-PDX
$155
6/4Tue
multi-stopFrontier
8h 59mPDX-MSP
6/6Thu
multi-stopFrontier
9h 46mMSP-PDX
$156
6/4Tue
nonstopAlaska Airlines
4h 05mPDX-ORD
6/8Sat
nonstopAlaska Airlines
4h 20mORD-PDX
$308
6/4Tue
multi-stopDelta
8h 45mPDX-ORD
6/12Wed
multi-stopDelta
7h 04mORD-PDX
$327
6/3Mon
multi-stopUnited Airlines
10h 52mPDX-ORD
6/6Thu
multi-stopUnited Airlines
7h 39mORD-PDX
$371
6/4Tue
nonstopUnited Airlines
3h 58mPDX-ORD
6/11Tue
nonstopUnited Airlines
4h 25mORD-PDX
$373
6/4Tue
nonstopDelta
3h 22mPDX-MSP
6/8Sat
nonstopDelta
3h 40mMSP-PDX
$457
5/31Fri
nonstopAlaska Airlines
3h 27mPDX-MSP
6/4Tue
nonstopAlaska Airlines
3h 52mMSP-PDX
$627

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Portland - Wisconsin Flights