$79 Find Cheap Flights from Portland to Wisconsin

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 7/16. 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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Cheap Flights from Portland to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$319
Madison
Madison1 stop$279
Appleton
Appleton1 stop$257
Green Bay
Green Bay1 stop$304
Wausau
Wausau1 stop$423
Duluth
Duluth1 stop$688
Chicago
Chicagononstop$209
Milwaukee
Milwaukee1 stop$319
Madison
Madison1 stop$279
Appleton
Appleton1 stop$257
Green Bay
Green Bay1 stop$304
Wausau
Wausau1 stop$423
Duluth
Duluth1 stop$688
Chicago
Chicagononstop$209

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

Vi, mai 1 - Ma, mai 5
United Airlines Logo
9:39 am - 11:35 am
PWM
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ORD
2h 56mnonstop
United Airlines Logo
10:48 am - 2:14 pm
ORD
-
PWM
2h 26mnonstop
$209United Airlines
Vi, mar 6 - Vi, mar 13
American Airlines Logo
5:40 pm - 7:50 pm
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ORD
3h 10mnonstop
American Airlines Logo
1:45 pm - 5:07 pm
ORD
-
PWM
2h 22mnonstop
$210American Airlines
Vi, mar 6 - Vi, mar 13
American Airlines Logo
5:40 pm - 7:50 pm
PWM
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ORD
3h 10mnonstop
American Airlines Logo
1:45 pm - 5:07 pm
ORD
-
PWM
2h 22mnonstop
$211American Airlines
Sâ, feb 21 - Jo, feb 26
United Airlines Logo
4:15 pm - 6:27 pm
PWM
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ORD
3h 12mnonstop
United Airlines Logo
4:10 pm - 11:20 pm
ORD
-
PWM
6h 10m
1 stop
$219United Airlines
Ma, mar 10 - Jo, mar 12
Delta Logo
12:51 pm - 4:43 pm
PWM
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ORD
4h 52m
1 stop
Delta Logo
7:00 am - 1:50 pm
ORD
-
PWM
5h 50m
1 stop
$229Delta
Mi, mar 4 - Sâ, mar 7
American Airlines Logo
12:29 pm - 5:13 pm
PWM
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ORD
5h 44m
1 stop
American Airlines Logo
2:05 pm - 5:27 pm
ORD
-
PWM
2h 22mnonstop
$230American Airlines
Ma, mar 10 - Jo, mar 12
Delta Logo
4:48 pm - 11:54 pm
PWM
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ORD
8h 06m
2 stops
Delta Logo
7:00 am - 1:50 pm
ORD
-
PWM
5h 50m
1 stop
$234Delta
Sâ, feb 7 - Lu, feb 9
United Airlines Logo
4:10 pm - 6:18 pm
PWM
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ORD
3h 08mnonstop
United Airlines Logo
4:15 pm - 11:30 pm
ORD
-
PWM
6h 15m
1 stop
$239United Airlines
Du, iun 21 - Sâ, iun 27
Sun Country Air Logo
12:40 pm - 2:48 pm
PWM
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MSP
3h 08mnonstop
Sun Country Air Logo
8:20 am - 11:59 am
MSP
-
PWM
2h 39mnonstop
$268Sun Country Air
Jo, mar 19 - Jo, mar 26
Southwest Logo
2:50 pm - 10:30 pm
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MKE
8h 40m
2 stops
Southwest Logo
4:20 pm - 12:05 am
MKE
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PWM
6h 45m
1 stop
$369Southwest
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.

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 November, when tickets cost $312 (return) on average. On the other hand, the most expensive months are September and August, when the average cost of round-trip tickets is $756 and $672 respectively.

Good to know

Low seasonMarch
Cheapest flight$79
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Portland to Minneapolis

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: Chicago $223 one-way - $358 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.
8.0
SouthwestOverall score based on 4266 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

Great flight but super high price. Glad it was a business trip and not personal

10.0 ExcellentPieter, Jan 2026
LGB - DAL
Read more Southwest reviews

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The flight crew where really good. Better then the crew from BNE to SFO

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

It was a good trip. Flight Attendants were friendly and responsive.

Qatar airways ,boarding arrangements at Hamid international airport could been better

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

My seat tv didn’t work the whole trip. And the seat space is too small despite being seated at the front.

The seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

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

Information on your arrival and departure airports