$99 Cheap American Airlines flights San Francisco (SFO) to Chicago (ORD)

Make use of the "Price (lowest to highest)" filter on Expedia to look for cheap American Airlines round-trip flights from $188 from SFO to ORD. Affordable one-way fares from $99 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 travel date to score cheaper fares on American Airlines flights from San Francisco Intl. Airport (SFO) 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 flights.*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.

The first flight from SFO to ORD with American Airlines departs at 5:20AM UTC-8. You'll touch down at 11:36AM UTC-6. The last American Airlines flight of the day leaves at 1:20PM UTC-8 and arrives at 7:41PM UTC-6. With around 20% fewer cancellations for early and mid-morning flights, setting off early is typically the wisest option.**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.