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

Price overview for flights from Chicago to Grand Cayman

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

  • $2026Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)03/11/202507:30 pm
    Grand Cayman, KY (GCM)Chicago, IL (ORD)03/25/202506:50 pm
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  • $2950Westjet flight Westjet 
    FromToDepartureTime
    Chicago, IL (MDW)Grand Cayman, KY (GCM)03/19/202501:16 pm
    Grand Cayman, KY (GCM)Chicago, IL (MDW)03/31/202501:50 pm
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  • $3002Westjet flight Westjet 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)03/26/202506:15 pm
    Grand Cayman, KY (GCM)Chicago, IL (ORD)04/03/202501:50 pm
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  • $4385Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)03/26/202510:45 pm
    Grand Cayman, KY (GCM)Chicago, IL (ORD)04/03/202501:50 pm
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  • $4893Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)03/25/202506:15 pm
    Grand Cayman, KY (GCM)Chicago, IL (ORD)04/01/202506:05 pm
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  • $1324Westjet flight Westjet 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)03/08/202506:45 am
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  • $1375Westjet flight Westjet 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)03/09/202506:15 pm
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  • $3097Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)03/09/202507:30 pm
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  • $3254Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)02/27/202506:26 pm
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  • $3450British Airways flight British Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)02/27/202509:56 pm
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