Nonstop flights from Chicago to Grand Cayman
2 airlines fly this route, with up to 2 flights a day.
ORDChicago O'Hare International
1,614 mi · 13 flights a week
GCMGrand Cayman Owen Roberts International
When they leave
Chicago time8:42a9:24aFirst departure 8:42 AM, last 9:24 AM
Two in the morning, 8:42 AM to 9:24 AM.
Every flight
Earliest first
Schedules last checked Sep 21, 2026. Times are local.
Flying from Chicago to Grand Cayman
United Airlines flies most often, daily on the Boeing 737. American Airlines flies 6 times a week on the Boeing 737.
There are 1 or 2 flights every day of the week. The first arrival in Grand Cayman is at 1:42 PM and the last at 2:35 PM. The flight covers 1,614 miles.
United Airlines is back on Oct 31. American Airlines starts on Nov 21.
Flying back, Grand Cayman to Chicago has 13 nonstop flights a week.
Return flights
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Find the cheapest day to fly from Chicago to Grand Cayman.
Schedules as of Oct 9, 2026.