$141 Cheap American Airlines flights Lexington (LEX) to Chicago (ORD)

You can discover cheap return American Airlines flights from $189 from LEX to ORD by organizing your results from "Price (lowest to highest)" on Expedia. Or search for deals from $141 for a one-way trip.**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 Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD). You can save 25% by booking your domestic flight 34 to 86 days in advance versus 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.* 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.

Leaving LEX at 6:50AM UTC-5, the first American Airlines flight to ORD arrives at 7:26AM UTC-6. Flying early means you'll be less likely to encounter delays or cancellations.* After something later? The last American Airlines flight from LEX to ORD departs at 3:38PM UTC-5 and touches down at 4:15PM UTC-6.*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.