What’s the cost of 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.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Planning flights between Portland and Chicago? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in Portland: Portland is the only airport in this city.
• Airports in Chicago: Chicago features 3 airports - Midway, O'Hare, Rockford.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

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 the best airlines and travel agencies.

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.