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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From $2026 / RT details

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

Recent Deals on Flights from Chicago to Grand Cayman:Roundtrip / Oneway

• $2026 Multiple Airlines 

  From	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

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• $3077 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Grand Cayman, KY (GCM)	01/22/2025	01:26 pm
  Grand Cayman, KY (GCM)	Chicago, IL (MDW)	01/27/2025	02:50 pm

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• $3131 Westjet 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	02/09/2025	04:58 pm
  Grand Cayman, KY (GCM)	Chicago, IL (ORD)	02/16/2025	02:50 pm

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• $1341 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Grand Cayman, KY (GCM)	01/22/2025	12:44 pm

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• $1375 Westjet 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	03/09/2025	06:15 pm

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• $3097 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	03/09/2025	07:30 pm

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• $3254 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	02/27/2025	06:26 pm

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• $3450 British Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	02/27/2025	09:56 pm

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