Cheap Flights from Portland to Chicago

Prices were available within the past 7 days and starts at $44 for one-way flights and $88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Reviews from verified customers

Mar 7, 2020

I had to pay for a backpack which was annoying and inconvenient. It was not the correct side according to the agent

Feb 22, 2020

Need more leg room

Feb 19, 2020

Wish there were power/usb outlets in all seats

Feb 19, 2020

Even though the plane was delayed, our steward was wonderful. When some tempers were running short, he was able to reframe the situation and regain control so that we had a good, safe trip and deboarding.

Feb 16, 2020

Staff was so warm and welcoming and wanted to be there! Such a different experience than united airlines. Seats were comfortable even in row 30. United has jammed in more seats which makes it a uncomfortable tight miserable experience.

Jan 30, 2020

Did not appreciate 30.00 fee for my carry on device .

Jan 9, 2020

Alaska Airlines is an amazing company!

Jan 1, 2020

I was really neither happy or sad about my flight. You need to give a neutral option.

Dec 29, 2019

Flight attendants Eileen and Fran (flight 690) were an example of what great employees should be like, from when we boarded to when we exited, we wanted for nothing. Just great overall

Dec 4, 2019

Need more space bigger restrooms and better seating options

Portland to Chicago route information

Origin Airport Portland Intl.
Destination Airport O'Hare Intl.
Airlines Serving Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, United
Flight Price $87
Distance 1,734 mi

Cheap PDX to ORD Flights