Direct flights from Chicago to Grand Cayman Island
All flights from ORD to GCM non-stop. There are direct flights from Chicago O Hare International, Illinois, USA to Grand Cayman (GCM), Cayman Islands every day of the week with United Airlines and American Airlines. The flight distance is 1622 miles and the trip usually takes about 3 hours and 45 minutes.
Airlines with non-stop routes:

United Airlines

American Airlines

Cayman Airways
No flights anymore
Flight schedule from Chicago to Grand Cayman Island 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 2025-03-15
Flight schedule from Chicago to Grand Cayman Island 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 2025-03-15
Chicago to Grand Cayman Island flight departures
Select a date to see all scheduled flight departures between ORD to GCM.
ORD - GCM information
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Distance1622 miles (2610 km)
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Flight time3 hours and 45 minutes
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Airlines
United
American Airlines
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AlliancesOne WorldSky TeamStar Alliance
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ClassesEconomyBusinessFirst Class
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United AircraftBoeing 737 Passenger
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American Airlines AircraftBoeing 737 Passenger
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Departure TerminalsTerminal 1 (United)Terminal 3 (American Airlines)
Unpublished Flight Rates From Chicago to Grand Cayman Island