$173 Cheap United flights Chicago (ORD) to Key West (EYW)

Make use of the “Price (lowest to highest)” filter on Expedia to find cheap United Airlines return flights from $303 from ORD to EYW. Affordable one-way tickets from $173 are also available.**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 return or one-way flights to Key West in September or August. You could find a cheap fare with United Airlines during these quieter months.

Begin your search one to three months ahead of your departure date to find cheaper fares on United Airlines flights from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Time it well, and you can enjoy significant savings on domestic trips.*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.

Depart on one of United Airlines’s 7 weekly direct flights from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). To view available options, enter your dates, destination and origin and hit search. Then select the “Nonstop” and “Airline” filters.

It takes around 3h 14m to fly nonstop from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) with United Airlines.

The first flight from ORD to EYW with United Airlines departs at 10:35AM UTC-6. You’ll land at 2:49PM UTC-5. The final United Airlines flight of the day leaves at 10:36AM UTC-6 and arrives at 2:50PM UTC-5. With 20% fewer cancellations for departures before midday, heading out early is often the wisest option.**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 United Airlines flights from O’Hare Intl. Airport (ORD).

A rewarding loyalty program and the ability to collect points through United Mileage Plus are the start of the reasons to travel from ORD to EYW with United Airlines. Plus, when you sign up to our One Key™ program, you can receive OneKeyCash™* on top of any airline loyalty program earnings. It’s yours to spend on future bookings.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

United Airlines typically uses Boeing 737-700 planes for journeys from O’Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). Keep in mind that aircraft type can change depending on operational demands, so the plane you catch might be different on your travel date.

Changes are typically free within 24 hours of making your booking, but your airline may add a charge after that. For further details about altering your reservation, go to your “Trips,” select your flight and click on “Manage Booking.” If you’d like the flexibility to adjust your plans without extra charges, check the “Changes included” or “No cancel fee” filter when organizing your trip.