Flights from Chicago (CHI) to Cayman Islands (Cayman Islands)

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Prices from $454 to $623

We'll show you the best deals by comparing tons of flights from Chicago to Cayman Islands across a wide range of airlines and travel agents. Compare the cheap flights along this route.

$454RT including taxes
Feb 10 2019 Feb 17 2019
7 nights
Chicago (CHI) to George Town (GCM)
Flying with: Cayman Airways
$623RT including taxes
Dec 09 2018 Dec 15 2018
6 nights
Chicago (ORD) to Cayman Brac (CYB)
Flying with: American Airlines

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