$120 Cheap American Airlines flights Aspen (ASE) to Chicago (ORD)

Apply the "Price (lowest to highest)" filter on Expedia to search for cheap American Airlines return flights from $191 from ASE to ORD. Affordable one-way fares from $120 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.

Search for cheap American Airlines flights from Pitkin County Airport (ASE) 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. No matter the fare class and itinerary, the best day to book a domestic flight is generally Sunday and the most expensive is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book 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.

Setting off from ASE at 12:27PM UTC-7, the earliest American Airlines flight to ORD arrives at 4:27PM UTC-6. Flying earlier in the day means you're less likely to experience cancellations.* Prefer to travel later? The last American Airlines flight from ASE to ORD departs at 3:12PM UTC-7 and touches down at 7:09PM 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.