How much should you expect to spend for a flight from Portland to Chicago?

Flight prices from Portland to Chicago change depending on demand and time of booking.

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

Studies show that flying midweek — like on a Tuesday or Wednesday — can be cheaper than weekend flights. Still, airfares change frequently, so check updated prices on Jetcost.

Which airports near Portland or Chicago offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

• Airports in Portland: Only Portland is currently operating.
• Airports in Chicago: 3 options available in Chicago - Midway, O'Hare, Rockford.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Adjust your flight filters for Portland – Chicago

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from the best travel agencies and carriers.

Other popular destinations

Planning a trip to United States? These cities are popular too: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.