What’s the cost of a flight from Portland Jetport 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.

Flying between Portland and Chicago? Consider these airports

Depending on your destination and where you’re starting from, it might make sense to look beyond the main hubs.

• Airports in Portland: Portland has only one airport in service, Portland - Jetport.
• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.

Check if your destination airport has a rail link — it can make getting around easier. Jetcost lets you view options from all Portland airports in a single search.

Plan smarter: flights from Portland Jetport to Chicago Midway

Find the flight that fits your plans with Jetcost. You can filter results by stops, agencies, budget, time of day, and airline — all in one search.

Other popular destinations

Travelers flying to United States also checked out: Atlanta, Los Angeles, Miami, New York City, Orlando.

Comparing offers from multiple agencies helps you find the best price for the same route. You can also spot exclusive deals from individual airlines right in the results list.