$183 Cheap American Airlines flights Chicago (ORD) to Lexington (LEX)

You'll find budget-friendly return American Airlines flights from $189 from ORD to LEX by filtering your results from "Price (lowest to highest)" on Expedia. Or search for options from $183 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 before your departure to score cheaper fares on American Airlines flights from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX). 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.* Get the timing right, 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.

The earliest American Airlines flight from ORD to LEX departs at 10:30AM UTC-6, touching down at 1:00PM UTC-5. If you want to set off later, the last American Airlines flight leaves ORD at 8:35PM UTC-6 and touches down at LEX at 11:05PM UTC-5. Flying before midday is often a smart choice as morning flights tend to experience 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.