$169 Cheap American Airlines flights Chicago (ORD) to San Jose (SJC)

Set the "Price (lowest to highest)" filter on Expedia to search for cheap American Airlines return flights from $371 from ORD to SJC. Affordable one-way tickets from $169 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.

Start searching one to three months ahead of your departure date to get cheap fares on American 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 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 your 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.

Search American Airlines's earliest flights from ORD to SJC by selecting the "Morning" and "Early Morning" filters. Not only will you arrive 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.