$127 Cheap Alaska Airlines flights Chicago (ORD) to San Jose (SJC)

Grab budget-friendly return Alaska Airlines flights from $236 from ORD to SJC by sorting your results from “Price (lowest to highest)” on Expedia. Or search for deals from $127 for a one-way trip.**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.

April is one of the cheapest months to jet off to San Jose with Alaska Airlines. You could also find great deals on return and one-way fares in November.

Start searching one to three months ahead of your departure date to find cheap fares on Alaska Airlines flights from O’Hare Intl. Airport (ORD) to Norman Y. Mineta San Jose Intl. Airport (SJC). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also cut 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 trips.*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.

To find out if there’s a direct trip from ORD to SJC with Alaska Airlines or another airline, select the “Nonstop” filter when browsing for tickets.

Browse Alaska Airlines’s earliest flights from ORD to SJC by using the “Early Morning” and “Morning” filters. Not only will you arrive at your destination sooner, early departures also experience 20% fewer 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.

Take an Alaska Airlines flight from O’Hare Intl. Airport (ORD) to San Jose, and you’re most likely to land at Norman Y. Mineta San Jose Intl. Airport (SJC). This is the airline’s primary hub here.

With top-tier customer service and a rewarding loyalty program, Alaska Airlines is a top choice for many passengers flying from ORD to SJC. 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 can be used on future getaways.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Changes are often free within 24 hours of making your booking, but your airline may charge a fee after that time. For more information about altering your reservation, check out your “Trips,” select your flight and click on “Manage Booking.” If you’d like the flexibility to adjust your plans without extra charges, check the “Changes included” and “No cancel fee” filters when planning your next escape.