$253 Cheap Delta flights Chicago (ORD) to Key West (EYW)

Grab budget-friendly return Delta Air Lines flights from $269 from ORD to EYW by sorting your results from “Price (lowest to highest)” on Expedia. Or look for options from $253 for a one-way trip.**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 one-way or round-trip flights to Key West in September or August. You could find an affordable fare with Delta Air Lines during these quieter months.

Search for cheap Delta Air Lines flights from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) one to three months prior to your departure. 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 type and itinerary, the best day of the week 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.

Enter your dates, press search and select the “Nonstop” filter on Expedia to browse any direct flights from ORD to EYW with Delta Air Lines or another carrier.

Sort your results by “Morning” and “Early Morning” to see the earliest flights from ORD to EYW. Taking off early means you’re 20% 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.

Get on a Delta Air Lines flight from O’Hare Intl. Airport (ORD) to Key West, and you’ll likely touch down at Key West Intl. Airport (EYW). This is the airline’s main hub in this destination.

Offering an excellent in-flight experience and a rewarding loyalty program, Delta Air Lines is the leading choice for many travelers flying from ORD to EYW. Plus, if you’re a Delta SkyMiles and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which you can put toward future travel.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Changes are generally free within 24 hours of making a booking, but your airline may charge you after that time. For more information about modifying your flights, head to your “Trips,” select your flight and click on “Manage Booking.” If you’d like the flexibility to change your plans without being charged, tick the “Changes included” and “No cancel fee” filters when organizing your next escape.