$114 Cheap American Airlines flights San Jose (SJC) to Chicago (ORD)

Finding cheap one-way American Airlines flights from SJC to ORD from $114 on Expedia is a cinch --- just filter by "Price (lowest to highest)." Alternatively, check out our affordable return fares from $371 for your next adventure.**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.

To find cheap American Airlines fares from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Securing domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also influence the price you pay. Sunday is usually the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your trip on a Sunday.**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.

Find American Airlines's earliest flights from SJC to ORD by selecting our "Morning" and "Early Morning" filters. Not only will you get to where you're going 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.