Direct flights from Key West to Chicago
All flights from EYW to ORD non-stop. There are direct flights from Key West International (EYW), Florida, USA to Chicago O Hare International (ORD), Illinois, USA with American Airlines and United Airlines. 21 weekly departures are currently scheduled on this route. Departure times range from 09:00 to 18:46 depending on the schedule period. The flight distance is 1261 miles (2029 km). Flight time ranges from 3 hours and 25 minutes to 4 hours and 1 minutes.
Key West
, USA
Flight schedule from Key West to Chicago with American Airlines
This is a weekly direct flight schedule for American Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-11-02
Flight schedule from Key West to Chicago with United Airlines
This is a weekly direct flight schedule for United Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-11-02
Key West to Chicago scheduled departures
Select a date to see every published non-stop departure between EYW and ORD.
EYW - ORD route facts
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Distance1261 miles (2029 km)
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Flight time3 hours and 25 minutes to 4 hours and 1 minutes
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Airlines American Airlines United
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Airline alliancesoneworld Star Alliance
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CabinsEconomy First
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Hub airportsAmerican Airlines: ORDUnited Airlines: ORD (Largest hub.)
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Arrival terminalsAmerican Airlines: Terminal 3United Airlines: Terminal 2 and Terminal 1
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AircraftAmerican Airlines: Embraer 170 and Embraer 175United Airlines: Embraer 175 (Enhanced Winglets) and Boeing 737-700 Passenger
