Flights From Chicago (CHI) to Grand Cayman (GCM)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Selected fares from Chicago to Grand Cayman

The cheapest prices found with in the last 7 days for return flights were CA $626 and CA $396 for one-way flights to Grand Cayman for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sat, Nov. 22 - Fri, Nov. 28
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
CA $626 Roundtrip, found 1 day ago
CA $626
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Nov. 22 from O'Hare Intl. to Owen Roberts Intl., returning Fri, Nov. 28, priced at CA $626 found 1 day ago
Air Canada
Sat, Nov. 22 - Fri, Nov. 28
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
CA $679 Roundtrip, found 1 day ago
CA $679
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Nov. 22 from O'Hare Intl. to Owen Roberts Intl., returning Fri, Nov. 28, priced at CA $679 found 1 day ago
Air Canada
Sat, Nov. 22 - Fri, Nov. 28
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
CA $850 Roundtrip, found 1 day ago
CA $850
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Nov. 22 from O'Hare Intl. to Owen Roberts Intl., returning Fri, Nov. 28, priced at CA $850 found 1 day ago