$167 Cheap American Airlines flights Chicago (ORD) to Key West (EYW)

Grab cheap return American Airlines flights from $296 from ORD to EYW by sorting your results from “Price (lowest to highest)” on Expedia. Or search for deals from $167 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.

Look for round-trip or one-way flights to Key West in September or August. You could find an affordable fare with American Airlines during these off-season months.

For cheap American Airlines fares from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW), start searching one to three months before your intended departure. Securing 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 impact the cost. Sunday is usually the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking 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.

American Airlines operates direct flights from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW), with 7 departures every week. Simply choose the “Nonstop” and “Airline” filters during your search on Expedia to show all direct American Airlines flights to EYW.

Take off from O’Hare Intl. Airport (ORD) for Key West Intl. Airport (EYW) on a direct American Airlines flight, and you’ll be airborne for around 3h 24m.

Jetting off from ORD at 8:10AM UTC-6, the first American Airlines flight to EYW lands at 12:34PM UTC-5. Flying earlier in the day means you’ll be less likely to encounter delays or cancellations.* After something later? The last American Airlines flight from ORD to EYW departs at 8:10AM UTC-6 and touches down at 12:34PM UTC-5.*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.

Key West Intl. Airport (EYW) is the primary Key West gateway for American Airlines flights from O’Hare Intl. Airport (ORD).

Chances are you’ll be flying on an Embraer 170 for your American Airlines flight from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). However, you may end up on an alternative aircraft if there are operational changes.

Depending on the type of ticket you purchased, a fee typically applies if you cancel or reschedule your booking more than 24 hours after it’s been confirmed. To secure flexible plane tickets, select our “Changes included” and “No cancel fee” boxes while searching for flights. For more details on changing or canceling your reservation, visit “Trips,” select your flight and click on “Manage Booking.”