$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 8/22. 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

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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$311
Madison
Madison1 stop$291
Appleton
Appleton1 stop$319
Green Bay
Green Bay1 stop$309
Wausau
Wausau1 stop$611
Minneapolis
Minneapolisnonstop$226
Chicago
Chicago1 stop$315
Duluth
Duluth1 stop$398
Milwaukee
Milwaukee1 stop$311
Madison
Madison1 stop$291
Appleton
Appleton1 stop$319
Green Bay
Green Bay1 stop$309
Wausau
Wausau1 stop$611
Minneapolis
Minneapolisnonstop$226
Chicago
Chicago1 stop$315
Duluth
Duluth1 stop$398

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

Thu, Jul 9 - Sun, Jul 12
Sun Country Air Logo
12:40 pm - 2:49 pm
PWM
-
MSP
3h 09mnonstop
Sun Country Air Logo
7:55 am - 11:37 am
MSP
-
PWM
2h 42mnonstop
$226Sun Country Air
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
$227Sun Country Air
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
$236Sun Country Air
Sat, Nov 21 - Sat, Dec 5
Delta Logo
3:00 pm - 8:11 pm
PWM
-
MSN
6h 11m
1 stop
Delta Logo
7:00 am - 1:22 pm
MSN
-
PWM
5h 22m
1 stop
$291Delta
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
6:00 am - 12:08 pm
PWM
-
MSN
7h 08m
1 stop
American Airlines Logo
7:47 am - 6:10 pm
MSN
-
PWM
9h 23m
2 stops
$296American Airlines
Sat, Nov 21 - Thu, Nov 26
Delta Logo
3:00 pm - 8:11 pm
PWM
-
MSN
6h 11m
1 stop
Delta Logo
7:00 am - 11:53 am
MSN
-
PWM
3h 53m
1 stop
$305Delta
Wed, Aug 19 - Mon, Aug 24
United Airlines Logo
5:15 am - 11:58 am
PWM
-
MSN
7h 43m
2 stops
United Airlines Logo
2:44 pm - 9:23 pm
MSN
-
PWM
5h 39m
1 stop
$310United Airlines
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
9:08 am - 12:47 pm
PWM
-
MKE
4h 39m
1 stop
American Airlines Logo
10:21 am - 6:06 pm
MKE
-
PWM
6h 45m
1 stop
$311American Airlines
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
6:00 am - 10:00 am
PWM
-
MKE
5h 00m
1 stop
United Airlines Logo
6:00 am - 2:38 pm
MKE
-
PWM
7h 38m
2 stops
$316United Airlines
Wed, Jul 22 - Sat, Aug 1
Southwest Logo
7:10 pm - 11:15 pm
PWM
-
MKE
5h 05m
1 stop
Southwest Logo
5:40 pm - 11:45 pm
MKE
-
PWM
5h 05m
1 stop
$317Southwest
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 August.

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 24% drop in price.
Most popular time to fly and prices are also 23% 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 $199 one-way - $328 round-trip; Chicago $231 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 4247 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

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.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

Crew was real good, flight was smooth and came in early.

The CRJ-900 was clean but the overhead air vents were broken in our First Class row, making the cabin very hot until about 30 mins into the flight. The flight attendants were both extremely apologetic and accommodating though so that is why I rated the flight as very good. They checked on us many times and truly showed they cared. The snacks for an hour and a half flight could be better. Would be nice if there was a small plated meal over convenient store snacks. WiFi also was not working. And it would be nice if Delta had adjustable headrests on these planes.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Both my flight where delayed Had 25min to make it to my transfer flight

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We were upgraded to First Class and it was a great flight

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We loved the steward on the plane. He made the night enjoyable

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

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

Information on your arrival and departure airports