MKE - PWM

$163 Find Cheap Flights from Milwaukee to Portland - 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 Milwaukee to Portland departing on 8/24. 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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Everything you should know

Cheapest round-trip
$325
Typical prices: $386-$520
Southwest
Tue 11/10Sat 11/14
MKE - PWM • 1 stop
Cheapest one-way
$163
Typical prices: $133-$190
Southwest
Mon 8/24
MKE - PWM • 1 stop
Top airlines
Cheapest • from $325 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Milwaukee and Portland. You'll need at least 1 connection.
Insights
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Top layover airports
Cheapest • Avg $411 (round-trip)
Shortest trip • 4h 29m (one-way)
Insights
Insights
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Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
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We hope you love your trip to Portland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Milwaukee to Portland (MKE-PWM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Portland 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 Milwaukee to Portland

Tue, Nov 10 - Sat, Nov 14
Southwest Logo
6:35 am - 12:15 pm
MKE
-
PWM
4h 40m
1 stop
Southwest Logo
5:25 am - 12:05 pm
PWM
-
MKE
7h 40m
1 stop
$325Southwest
Mon, Aug 24 - Mon, Aug 31
United Airlines Logo
10:19 am - 5:42 pm
MKE
-
PWM
6h 23m
1 stop
United Airlines Logo
6:53 pm - 11:37 pm
PWM
-
MKE
5h 44m
1 stop
$325United Airlines
Sat, Sep 19 - Sat, Sep 26
American Airlines Logo
7:43 am - 4:24 pm
MKE
-
PWM
7h 41m
1 stop
American Airlines Logo
5:30 am - 9:46 am
PWM
-
MKE
5h 16m
1 stop
$325American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:00 pm - 11:37 pm
MKE
-
PWM
4h 37m
1 stop
American Airlines Logo
6:02 am - 12:56 pm
PWM
-
MKE
7h 54m
1 stop
$325American Airlines
Sat, Sep 12 - Sat, Sep 19
Delta Logo
8:05 am - 4:01 pm
MKE
-
PWM
6h 56m
1 stop
Delta Logo
6:30 am - 11:37 am
PWM
-
MKE
6h 07m
1 stop
$325Delta
Sat, Nov 14 - Tue, Nov 17
Delta Logo
1:30 pm - 9:05 pm
MKE
-
PWM
6h 35m
1 stop
Delta Logo
5:29 pm - 10:00 pm
PWM
-
MKE
5h 31m
1 stop
$325Delta
Tue, Oct 13 - Sat, Oct 17
United Airlines Logo
5:00 am - 10:40 am
MKE
-
PWM
4h 40m
1 stop
United Airlines Logo
6:00 am - 11:30 am
PWM
-
MKE
6h 30m
1 stop
$325United Airlines
Tue, Oct 27 - Sat, Oct 31
Southwest Logo
5:45 am - 3:30 pm
MKE
-
PWM
8h 45m
2 stops
Southwest Logo
5:35 am - 10:40 am
PWM
-
MKE
6h 05m
1 stop
$330Southwest
Thu, Aug 20 - Sun, Aug 23
Multiple Airlines Logo
12:10 pm - 9:12 am
MKE
-
PWM
20h 02m
1 stop
Multiple Airlines Logo
7:00 am - 11:13 am
PWM
-
MKE
53h 13m
2 stops
$459Multiple Airlines
Thu, Sep 24 - Sat, Sep 26
Multiple Airlines Logo
10:10 am - 7:34 pm
MKE
-
PWM
8h 24m
1 stop
Multiple Airlines Logo
7:00 am - 9:22 am
PWM
-
MKE
27h 22m
2 stops
$473Multiple Airlines
Booking Insights

KAYAK's insights & trends for Milwaukee to Portland flights

Get data-powered insights and trends into flights from Milwaukee to Portland to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Milwaukee to Portland, Maine?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Milwaukee to Portland, Maine departing in October.

Flight prices are below average for this route right now.

Flights to Portland, Maine from Milwaukee usually cost between $462 and $596 in October.
The lowest price found in the past 5 days was $325 on United Airlines (Oct 3-Oct 7).

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Portland, 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 Milwaukee to Portland is April, where tickets cost $0 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $858 and $536 respectively.

Good to know

Cheapest flight

$163
Most popular time to fly with an average 2% increase in price.
Flight from Milwaukee to Portland

When to book flights from Milwaukee to Portland

Are your dates flexible? Find out the best times to travel from Milwaukee to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Milwaukee to Portland

  • What is the cheapest flight from Milwaukee to Portland?

    In the last 5 days, the lowest price for a flight from Milwaukee to Portland was $163 for a one-way ticket and $325 for a round-trip.

  • Do I need a passport to fly between Milwaukee and Portland?

    No

  • Which aircraft models fly most regularly from Milwaukee to Portland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Milwaukee to Portland?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Milwaukee and Portland, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Milwaukee to Portland, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Milwaukee to Portland are Southwest and Delta. With an average price for the route of $521 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $416 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Milwaukee to Portland?

    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 Milwaukee to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Milwaukee 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 Milwaukee to Portland?

    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 Portland with an airline and back to Milwaukee with another airline. Booking your flights between Milwaukee and PWM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Portland?

    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 Portland from Milwaukee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Milwaukee to Portland

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Portland. 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 Milwaukee to Portland? 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 4229 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

6.0 GoodVera, Jul 2026
MCO - BNA
Read more Southwest reviews

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

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

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

My wallet fell out of my pocket ( my fault). Staff claimed they looked while cleaning. Said they didn't find it, but was actually found in Washington DC on the plane. Which mean either they didn't look or don't do a good job of cleaning. Now I have to pay 27 dollars to get it shipped back and have no wallet for my entire vacation

This flight 1810 on 7/30 from EWR to DFW got 4 hours delay. this round trip experience is bad, my AA flight 618 from DFW to EWR on 7/28 was redirected to PIT and totally delayed about 9 hours due to mixed of weather and AA IT outage and then on the way back delayed for 4 hours. Lucky, i changed my flight to UA on the way back. i don't like AA anymore. i will consider other airline options in the future.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

90 min delay for a food cart that needed to be fixed.

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

Information on your arrival and departure airports