Find out what a flight from Portland to Chicago Midway might cost

Prices vary based on date, airline, and availability. Compare several options if you're flying between Portland and Chicago.

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Which airports are most convenient between Portland and Chicago?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in Portland: Only Portland is currently active.
• Airports in Chicago: In Chicago you can fly to/from 3 airports - Midway, O'Hare, Rockford.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

Find the best flight from Portland to Chicago Midway

With Jetcost, you can filter results by flight time, airline, price range, and layovers. Choose direct or connecting flights, round-trip or one-way, and compare offers from Ryanair, Easyjet, British Airways, and more.

Other popular destinations

Searching for flights to United States? Travelers also looked at: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Use filters to exclude options that don’t match your budget or travel preferences and personalize your search for Portland – Chicago Midway flights.