Cheap flights from Portland, Or to Chicago, United States (PDX - CHI)

Flying from Portland, Or to Chicago can be expensive. Our search helps you compare cheap flights, airfare deals, and flight tickets across airlines and agencies so you can book at the best price.

We scan trusted travel agencies and airline booking systems for the route Portland, Or - Chicago (PDX - CHI). We do not sell tickets or add fees - you choose where to buy.

Airfares vary by date, time, and airport. Use filters to find the best option by departure/arrival time, number of stops, airline or alliance, and booking channel.

If your dates are flexible, check the low-fare calendar to find the cheapest days. Booking round-trip in one order often reduces fees, and prices usually rise as departure approaches.

We also recommend you to look through the prices for return tickets from Chicago to Portland, Or.

Airfares found by our users in the past 24 hours

The cheapest flight from Portland, Or to Chicago is 17 717र on Alaska Airlines, departing on 06/13/2026 - 08:56 and returning on 06/26/2026 - 15:20.
The price for these dates could change. Use search to get the best price.

Average round-trip airfares from Portland, Or to Chicago by months

MonthRound-Trip
January 2026find now
February 2026find now
March 2026find now
April 2026find now
May 2026find now
June 202613.06 - 26.06from 17 717र
July 2026find now
August 2026find now
September 2026find now
October 2026find now
November 2026find now
December 2026find now

Prices shown are based on searches from the last few days. Ticket prices can change and depend on availability at the time of booking.

Airlines are flying from Portland, Or to Chicago

Southwest Airlines
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