$146 Cheap American Airlines flights Charlottesville (CHO) to Chicago (ORD)

You can find budget-friendly return American Airlines flights from $229 from CHO to ORD by filtering your results from "Price (lowest to highest)" on Expedia. Or search for deals from $146 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.

Search for cheap American Airlines flights from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD) one to three months prior to your departure day. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare type and journey, the ideal day to book a domestic flight is generally Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**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 departure from CHO to ORD with American Airlines, filter your results by "Early Morning" and "Morning." Choosing an early flight usually 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.