$134 Find Cheap Flights from Portland to Wisconsin - Compare and Save

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Cheap Flights from Portland to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Milwaukee
Milwaukee1 stop$267
Madison
Madison1 stop$345
Appleton
Appleton1 stop$349
Green Bay
Green Bay1 stop$339
Wausau
Wausau2 stops$1,020
Minneapolis
Minneapolis1 stop$341
Chicago
Chicago2 stops$344
Duluth
Duluth2 stops$369
Milwaukee
Milwaukee1 stop$267
Madison
Madison1 stop$345
Appleton
Appleton1 stop$349
Green Bay
Green Bay1 stop$339
Wausau
Wausau2 stops$1,020
Minneapolis
Minneapolis1 stop$341
Chicago
Chicago2 stops$344
Duluth
Duluth2 stops$369
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?

Flight prices are below average for this route right now.

Flights to Wisconsin from Portland, Maine usually cost between $487 and $597 in November.
The lowest price found in the past 5 days was $267 on United Airlines (Nov 14-Nov 18).

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

The cheapest month for flights from Portland to Wisconsin is February, when tickets cost $344 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $593 and $537 respectively.

Good to know

Low season

February

Cheapest flight

$134
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Portland to Milwaukee

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 $284 one-way - $399 round-trip; Chicago $229 one-way - $422 round-trip

Reviews of the top 4 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.
7.9
SouthwestOverall score based on 4220 reviews
7.0Food
7.4Entertainment
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

Friendly crew. Snacks were carb-heavy. Flight was quite delaye

6.0 GoodChris, Oct 2026
Read more Southwest reviews

Friendly crew. Snacks were carb-heavy. Flight was quite delaye

The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.

the flight was significantly delayed. Not much was done by the airline to compensate passengers

the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.

Had to walk back and forth between concourses to figure out which gate I was supposed to be at. The app and the flight board in the airport had different gates listed. Was told numerous times to check bags only to get on the plane and find that there was plenty of room for bags. The flight was over an hour late which had me landing after the last train departed. WiFi was unusable

My experience was okay I changed my returning flight and I was charged extra money which I dont think should be the case, especially because I experienced small delays from my going flight. And many flights were either canceled or delayed after my original flight time. I believe some customers should have the ability to change flights due to certain situations

I've taken four flights with Southwest within the last three months and every single flight was delayed.

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.

Gate agents call groups one and two and give about 3-5 minutes for each group to board, then the call groups three and four together and it causes a bottleneck in the line. Give each group 3-5 minutes to board before calling the next group.

All was fine. Small plane so no food or entertainment.

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.

Worst boarding experience, flight extremely delayed causing super tight connect and deplaning was a disaster as ppl were pushing and shoving to get off. Then after flying over 8 hours had to get off a job to next flight. Limited beverage service in Business class (water or white wine) no food. The plane was very cold (temperature) so uncomfortable

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

Really delayed, no effort to support customers other than “sometimes we run late.”

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. .

Our gate was changed several times, and the gate agents were just as in the dark as all of us in knowing when our plane would arrive at PHL.

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

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..

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.

More options for your flight from Portland to Wisconsin

Complete your trip to Wisconsin with a hotel stay or car rental