There are several airlines that operate frequent flights from Portland (PDX) to Chicago (ORD) including

• Alaska Airlines with 234 flights a week
• Delta Air Lines with 95 flights a week
• American Airlines with 60 flights a week
• United Airlines with 36 flights a week
• with 5 flights a week

The earliest flight leaves Portland Intl. Airport at 00:34 and arrives at O'Hare Intl. Airport at 04:59. The last flight of the day departs Portland at 23:59 and arrives at Chicago at 20:36.

The flight distance from Portland to Chicago is about 2806 km, the shortest flight is 03 hours 47 minutes with United Airlines.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Portland Chicago flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Portland to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Portland to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!