Compare Chicago to Cayman Islands flight deals starting at $562

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Find flights from Chicago (ORD) to Cayman Islands

Chicago (ORD) to Grand Cayman (GCM)

Depart Fri 30 Nov 2018,
Return Sat 15 Dec 2018
from$ 562*Viewed: 2 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.
Man guiding a sailboat near the shore in the Cayman Islands

Plan ahead for flights from Chicago to Cayman Islands

from
to
Type
Dates
Price*
Chicago (ORD)
to Grand Cayman (GCM)
Roundtrip
Depart Fri 11 Jan 2019
Return Sat 26 Jan 2019
from$ 562*Viewed: 2 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.