Cheap flights from Milwaukee to Portland from $156

The cheapest month to fly to Portland from Milwaukee is in May. Flight prices, which tend to average around $387, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in May, then you should wait until January to fly from Milwaukee, when ticket prices are also cheap, with an average price of $409.

You are more likely to see cheaper flights to Portland from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $452 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Milwaukee for as low as $378 on momondo.

You could potentially save up to 3% on your flight if you consider stops on a Milwaukee to Portland flight.

As of August 2026, prices for Milwaukee to Portland flights are approximately 38% more expensive when compared to flights at the same time last year.

Southwest, Frontier, and United Airlines are the most popular carriers operating from Milwaukee-Mitchell to Portland

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Portland from Milwaukee according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 7 different airlines that fly to Portland on a routine basis, so you have a few additional options to choose from.

Minneapolis (MSP) was the most common stop: 71% of momondo users choosing 1-stop flights on this route connected there.

Flights via Minneapolis (MSP) offer the lowest average round-trip price of $641.

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 6h 09m.

Minneapolis (MSP) has the shortest average layover time for this route: 1h 08m.