Cheap flights from Milwaukee to Portland

One-way fares from $332 · MKE → PDX · prices found by travellers in the last 48 hours

Compare all dates Portland → Milwaukee
Cheapest fare
$332

Alaska Airlines · Sat, Nov 14

Cheapest month
November

from $332

Direct flights
Not recently

Usually 1+ stop

Quickest trip
5h 26m

2,760 km

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Cheapest month to fly from Milwaukee to Portland

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $332

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Alaska Airlines
Depart16:40 Sat, Nov 14MKE → PDX 5h 26m · 1 stop
$332one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Portland

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in PortlandCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in PortlandTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in PortlandPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in PortlandCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Milwaukee to Portland

Milwaukee (MKE) and Portland (PDX) are about 2,760 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 5h 26m. Over the next few months, one-way fares start from $332, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Milwaukee to Portland?

The cheapest one-way fare we've seen recently is $332 with Alaska Airlines, departing Saturday, November 14, 2026.

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

November 2026 currently has the lowest fares, from $332 one way.

Are there direct flights from Milwaukee to Portland?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Milwaukee to Portland?

The quickest journey we've seen takes about 5h 26m. Milwaukee and Portland are around 2,760 km apart.

Which airlines fly from Milwaukee to Portland?

Recent fares on this route were with Alaska Airlines.

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