Cheap flights from Chicago to Cayman Islands

Travel > Caribbean > Cayman Islands

Check our current prices for flights from Chicago to Cayman Islands. 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 Cayman Islands, you will need to run a search below.

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From $3178 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Grand Cayman airfares from $3178/RT are provided by Cheapoair.com. Outbound flight is leaving on 12/29/2024, 05:04 pm from Chicago Midway (MDW) airport and arrives at Grand Cayman Roberts (GCM) at 01:49 pm. The flight time is 20 hours and 45 minutes. The Returning flight departes on 01/12/2025, 02:50 pm (other return dates are also available). Date posted: 12 Nov 2024

Price evolution for flights From Chicago To Cayman Islands

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

• $3178 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Grand Cayman, KY (GCM)	12/29/2024	05:04 pm
  Grand Cayman, KY (GCM)	Chicago, IL (MDW)	01/12/2025	02:50 pm

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• $3310 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Grand Cayman, KY (GCM)	01/04/2025	05:04 pm
  Grand Cayman, KY (GCM)	Chicago, IL (MDW)	01/13/2025	02:50 pm

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• $3889 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Grand Cayman, KY (GCM)	12/28/2024	05:04 pm
  Grand Cayman, KY (GCM)	Chicago, IL (MDW)	01/05/2025	02:50 pm

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• $1338 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Grand Cayman, KY (GCM)	01/19/2025	11:19 am

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• $1654 Westjet 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	01/05/2025	07:00 am

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• $1670 Westjet 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	01/04/2025	05:30 pm

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• $2050 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Grand Cayman, KY (GCM)	01/05/2025	05:04 pm

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• $3540 British Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Grand Cayman, KY (GCM)	01/05/2025	09:45 pm

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