United Airlines
Star Alliance
Did you mean flights from Grand Cayman to Chicago?
United States
O'Hare International Airport
Switch direction
Cayman Islands
Owen Roberts International Airport
Click to show full flight schedule
Scan through all non-stop flights from Chicago to Grand Cayman. The full flight schedule below gives an overview of all non-stop flights from ORD to GCM, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Grand Cayman is a tropical destination known for its warm climate, with temperatures between 25°C and 30°C (77°F to 86°F) throughout the year. The area is characterized by high humidity and frequent rainfall.
Being located north of the equator, Grand Cayman experiences its dry season from November to April, making this the perfect time to visit. In this period, you can expect mostly dry conditions, while the wet season will see days of rain. Humidity and temperatures are consistently high all year long.
In total there are 2 airlines operating nonstop flights from Chicago ORD to Grand Cayman GCM. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their ORD GCM flight schedule.
Flights from ORD to GCM are operated 7 times a week, with an average of 1 flight per day. Departure times vary between 08:10 - 09:31. The earliest flight departs at 08:10, the last flight departs at 09:31. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
You can fly in Economy and Business Class. Premium Economy and First Class are not available on this route (at least not as a non-stop flight).
The fastest direct flight from Chicago to Grand Cayman takes 3 hours and 59 minutes. The flight distance between Chicago and Grand Cayman is 1,612 miles (or 2,594 km).
There is 1 airport in Grand Cayman: Owen Roberts International Airport (GCM).
There are 7 flights per week flying from Chicago to Grand Cayman (as of April 2026).
3 hours and 59 minutes is the average flight time from Chicago to Grand Cayman.
The distance from Chicago to Grand Cayman is 1,612 miles (2,594 kilometers).
American Airlines and United Airlines are flying nonstop from Chicago to Grand Cayman.
Oneworld and Star Alliance are flying nonstop from Chicago to Grand Cayman.
You can fly non-stop in Economy and Business Class.
Aircraft types that fly from Chicago to Grand Cayman:
The earliest flight departs at 08:10 from Chicago and arrives at 12:56 at Grand Cayman.
The latest flight departs at 09:31 from Chicago and arrives at 14:35 at Grand Cayman.
1,612 miles (2,594 km) · 3h 59m
08:45
12:45
United Airlines
Star Alliance
UA 342
United Airlines
Boeing 737-800
Y
W
J
F
09:29
13:30
United Airlines
Star Alliance
UA 342
United Airlines
Boeing 737 MAX 9
Y
W
J
F
Click to Check Prices
