How much is a flight from Portland to Chicago Midway?

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

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Portland - Chicago Midway route.

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.

Flight filters for the route Portland – Chicago Midway

Customize your search on Jetcost to focus only on flights that suit your needs. Whether you want a direct connection, specific airline, or shorter layover, filters help you find it faster.

Other popular destinations

Flights to United States are often searched alongside: Atlanta, Los Angeles, Miami, New York City, Orlando.

The cheapest flights might leave at odd hours or arrive at less central airports — keep that in mind. If you travel often, you can always select your trusted airlines from the available options.