Cheap flights from Chicago to Grand Cayman
Travel > Caribbean > Cayman Islands > Chicago to Grand Cayman flights
Check our current prices for flights from Chicago to Grand Cayman. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Grand Cayman, you will need to run a search below.
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Book your flight now with Cheapoair.com and save!
Cheap Grand Cayman airfares from $2026/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/11/2025, 07:30 pm from Chicago O`hare (ORD) airport and arrives at Grand Cayman Roberts (GCM) at 04:55 pm. The flight time is 21 hours and 25 minutes. The Returning flight departes on 03/25/2025, 06:50 pm (other return dates are also available). Date posted: 14 Jan 2025
Price evolution for flights From Chicago To Grand Cayman
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Recent Deals on Flights from Chicago to Grand Cayman:Roundtrip / Oneway
- $2026
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 03/11/2025 07:30 pm Grand Cayman, KY (GCM) Chicago, IL (ORD) 03/25/2025 06:50 pm - $2950
Westjet
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Grand Cayman, KY (GCM) 03/19/2025 01:16 pm Grand Cayman, KY (GCM) Chicago, IL (MDW) 03/31/2025 01:50 pm - $3002
Westjet
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 03/26/2025 06:15 pm Grand Cayman, KY (GCM) Chicago, IL (ORD) 04/03/2025 01:50 pm - $4385
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 03/26/2025 10:45 pm Grand Cayman, KY (GCM) Chicago, IL (ORD) 04/03/2025 01:50 pm - $4893
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 03/25/2025 06:15 pm Grand Cayman, KY (GCM) Chicago, IL (ORD) 04/01/2025 06:05 pm - $1324
Westjet
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 03/08/2025 06:45 am - $1375
Westjet
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 03/09/2025 06:15 pm - $3097
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 03/09/2025 07:30 pm - $3254
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 02/27/2025 06:26 pm - $3450
British Airways
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Grand Cayman, KY (GCM) 02/27/2025 09:56 pm
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