$206 Find Cheap Flights from Portland to Wisconsin - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 26% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Milwaukee
5h 30m2 stops
from $347per person
Green Bay
4h 45m2 stops
from $354per person
Madison
5h 28m2 stops
from $359per person
Appleton
5h 52m3 stops
from $364per person
Explore the map
Booking Insights

Price, demand and travel trends for Portland to Wisconsin flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Portland to Wisconsin recently?

Here are the cheapest round-trip fares from Portland to Wisconsin on KAYAK in the last week:

• Milwaukee-Mitchell (MKE) from $347
• Green Bay Austin-Straubel (GRB) from $354
• Madison Truax Field (MSN) from $359

How do fares into airports in Wisconsin compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Wisconsin from Portland are:

• Appleton Intl (ATW) (avg. price $398)
• Madison Truax Field (MSN) (avg. price $440)
• Green Bay Austin-Straubel (GRB) (avg. price $481)

What's the cheapest month to fly from Portland to Wisconsin?

February is typically the cheapest month to fly from Portland to Wisconsin, with round-trip fares averaging $348. December and November are usually the most expensive, averaging $627 and $520, respectively.

How do fares from Portland to Wisconsin vary by day of the week?

On average, Wednesday is the cheapest day to fly from Portland to Wisconsin and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 55% more expensive to fly on a Sunday compared to Wednesday.

What's the best time of day to fly from Portland to Wisconsin?

It's cheapest to fly to Wisconsin in the afternoon with average prices of $439. The evening is the most expensive time to fly, with average prices of $475.

Key details for Portland to Wisconsin flights

Low season

January

Cheapest flight

$206
Beat the crowds with an average 42% drop in travelers.
The most popular month to fly with an average 27% increase in travelers.
One-way flight from Portland to Milwaukee

Your Portland to Wisconsin flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Portland to Wisconsin?

    Yes. Fares from Portland to Wisconsin are low right now. As a rule of thumb, a round-trip under $379 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Portland to Wisconsin?

    Over the past 12 months, round-trip fares from Portland to Wisconsin have typically cost between $379 and $577.

  • What are the main airports serving Wisconsin?

    There are 15 airports in Wisconsin. 50% of KAYAK users choose Milwaukee-Mitchell (MKE) as their arrival airport, while 35% choose Madison Truax Field (MSN).

  • Which airlines fly nonstop from Portland to Wisconsin?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Portland to Wisconsin. One-stop options include:

    • American Airlines
    • United Airlines
    • Southwest

  • Which destinations in Wisconsin can I fly nonstop from Portland?

    Based on the flight schedule for the next 3 months, there are no nonstop flights from Portland to Wisconsin. The most popular destination you can reach with one stop is Milwaukee.

  • Which cabin classes are available from Portland to Wisconsin?

    On flights from Portland to Wisconsin you can only book Economy Class.

  • What are some popular landmarks around Wisconsin?

    Wisconsin is home to many popular sights. KAYAK travelers' favorites include:

    • Fiserv Forum
    • Riverside Theater
    • Henry W. Maier Festival Park
    • Pabst Theater

Your guide to booking Portland to Wisconsin flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in February to save some money. It's typically the cheapest month on this route, while flights in December will cost you the most.
  • Fly out on a Wednesday to get the cheapest fares. Avoid Sunday flights, which are about 55% more expensive.
  • If you're watching your budget, fly into Appleton Intl (ATW) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Milwaukee, the most popular destination in Wisconsin. From there, it's easy to continue on to other popular spots such as Madison, Wisconsin Dells and Green Bay.

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.
8.0
SouthwestOverall score based on 4219 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

Terrible, decided to delay our flight since another flight require a flight captain

2.0 MediocreChih Hsuan, Nov 2026
Read more Southwest reviews

Terrible, decided to delay our flight since another flight require a flight captain

staff and crew were great but the flight delays for the last few flights are insane. After a long day of work and you will get a notification of flights delay is not the message we want to see. And for some reason it keeps happening often this year.

I love southwest. I can not wait until all the planes convert to the upgraded planes. I love the charging option and the newer seats. Thank you from a very loyal Southwest customer.

My return flight was much better than the flight there! I paid for seat to Veagas but not the return. Thankgoodness they assigned me a seat with additional leg room as I have back and leg problems. I really appreciate it. With the flight already being super expensive due to gas prices and having to pay for bags (now) I needed to save some money.

My first flight from LGA to STL was not good. They didn't do service until over halfway through the flight, the internet didn't really work, and the crew all seemed like they didn't want to be there.

We were stressed about landing as our connecting flight was about to start boarding, being unfamiliar with the airport or where the gates were. We exited the plane to discover we were at the gate we needed. We would be getting back on the same plane but nobody told us we could have just stayed onboard. My wife and I were seated on aisle seats across from each other. We asked if there was a way we could sit together. Once we were at cruising altitude they let us move to an unoccupied row so that was nice.

It’s Southwest. The seats are small, the snacks are meh, it’s $50 to check a bag. It’s exactly fine. Could have been better. Could have been worse. It’s not Spirit

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.

Deplorable not to have WiFi on 5 hr cross country flight and spend thousands of dollars

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