$69 Cheap Alaska Airlines flights San Diego (SAN) to Chicago (ORD)

You'll find affordable round-trip Alaska Airlines flights from $142 from SAN to ORD by sorting your results from "Price (lowest to highest)" on Expedia. Or look for bargains from $69 for a one-way journey.**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.

Begin your search one to three months ahead of your travel date to score cheaper fares on Alaska Airlines flights from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it's 6% cheaper on average than a Monday, the most expensive day to book.* Get the timing right, and you can enjoy significant savings on domestic journeys.*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.

Search Alaska Airlines's earliest flights from SAN to ORD by selecting the "Early Morning" and "Morning" filters. Not only will you arrive at your destination sooner, early departures also have a 20% less chance of being canceled.**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.

Alaska Airlines makes traveling from SAN to ORD more comfortable with a rewarding loyalty program and top-tier customer service. You could even start collecting points with Mileage Plan. Remember to join our free One Key™ rewards program to earn OneKeyCash™*, which can be redeemed on future bookings.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.