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

You’ll find affordable round-trip Alaska Airlines flights from $242 from SAN to ORD by sorting your results from “Price (lowest to highest)” on Expedia. Or look for bargains 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.

Browse for one-way or return flights to Chicago in January or February. You could find an affordable fare with Alaska Airlines during these off-season months.

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.

Enter your dates, press search and check the “Nonstop” filter on Expedia to browse any direct flights from SAN to ORD with Alaska Airlines or other carriers.

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.

O’Hare Intl. Airport (ORD) is the primary Chicago hub for Alaska Airlines flights from San Diego Intl. Airport (SAN).

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.

Depending on the type of ticket you purchased, a fee is typically charged if you modify or cancel your flight more than 24 hours after it’s confirmed. To find plane tickets with more flexibility, select our “No cancel fee” or “Changes included” filter while looking for flights. For additional information on changing or canceling your reservation, go to “Trips,” select your flight and tick “Manage Booking.”