Cheap American Airlines flights White Plains (HPN) to Chicago (ORD)

Make use of the "Price (lowest to highest)" filter on Expedia to search for cheap American Airlines return flights from HPN to ORD. Affordable one-way options are available too.**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.

For cheap American Airlines fares from Westchester County Airport (HPN) to O'Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also affect how much you pay. Sunday is usually the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by choosing to book on a Sunday.**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 HPN to ORD departs at 7:15AM UTC-5, landing at 9:00AM UTC-6. If you'd like to jet off later in the day, the last American Airlines flight leaves HPN at 4:30PM UTC-5 and lands at ORD at 6:12PM UTC-6. Flying earlier is generally a good idea as morning and mid-morning flights are less likely to experience 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.