Cheap Alaska Airlines flights Palm Springs (PSP) to Chicago (ORD)

Make use of the "Price (lowest to highest)" filter on Expedia to search for cheap Alaska Airlines round-trip flights from $250 from PSP to ORD. Affordable one-way fares are available as well.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Look for cheap Alaska Airlines flights from Palm Springs Intl. Airport (PSP) to O'Hare Intl. Airport (ORD) one to three months before your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. No matter the fare type and journey, the best day to book a domestic flight is usually Sunday and the most expensive tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

Filter your results by "Morning" and "Early Morning" to find the earliest departures from PSP to ORD. Setting off early means you're less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.

With an excellent in-flight experience and a rewarding loyalty program, Alaska Airlines is a popular option for many travelers flying from PSP to ORD. What's more, if you're a Mileage Plan and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which you can put toward future travel purchases.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.