$152 Cheap American Airlines flights Key West (EYW) to Chicago (ORD)

Apply the “Price (lowest to highest)” filter on Expedia to look for cheap American Airlines round-trip flights from $303 from EYW to ORD. Affordable one-way tickets from $152 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.

Look for round-trip or one-way flights to Chicago in January or February. You could find a cheap fare with American Airlines during these off-peak times.

Search for affordable American Airlines flights from Key West Intl. Airport (EYW) to O’Hare Intl. Airport (ORD) one to three months ahead of your departure date. 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. Regardless of fare class and itinerary, the best day to book a domestic flight is usually Sunday and the most expensive day 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.

American Airlines has direct flights from Key West Intl. Airport (EYW) to O’Hare Intl. Airport (ORD), with 7 departures each week. Just choose the “Nonstop” and “Airline” filters while searching on Expedia to show all direct American Airlines flights to ORD.

Depart Key West Intl. Airport (EYW) for O’Hare Intl. Airport (ORD) on a direct American Airlines flight, and you’ll be airborne for about 3h 31m.

The earliest American Airlines flight from EYW to ORD departs at 1:06PM UTC-5, arriving at 3:37PM UTC-6. If you want to head off later, the last American Airlines flight leaves EYW at 1:06PM UTC-5 and lands at ORD at 3:37PM UTC-6. Flying before midday is often a smart choice as 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.

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

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

Changes are often free within 24 hours of booking, but your airline may charge you after that time. For more details about modifying your flights, head to your “Trips,” select your flight and click on “Manage Booking.” If you’d like the freedom to adjust your plans without additional charges, tick the “Changes included” or “No cancel fee” filter when organizing your next getaway.