$89 Cheap American Airlines flights Charleston (CRW) to Chicago (ORD)

You can discover budget-friendly return American Airlines flights from $168 from CRW to ORD by organizing your results from "Price (lowest to highest)" on Expedia. Or search for options from $89 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.

Begin your search one to three months ahead of your departure date to find cheap fares on American Airlines flights from Yeager Airport (CRW) 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 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.* Time it well, 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 the earliest departures from CRW to ORD with American Airlines, filter your search by "Early Morning" and "Morning." Choosing an early flight generally means cancellations are less likely.**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.