Chicago to Grand Cayman Flights (CHI-GCM) from $205

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Selected fares from Chicago to Grand Cayman

The cheapest prices found with in the last 7 days for return flights were $490 and $205 for one-way flights to Grand Cayman for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sun, May 5 - Sun, May 12
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$490 Roundtrip, found 23 hours ago
$490
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Sun, May 5 from O'Hare Intl. to Owen Roberts Intl., returning Sun, May 12, priced at $490 found 23 hours ago
JetBlue Airways
Fri, May 10 - Mon, May 13
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$537 Roundtrip, found 2 days ago
$537
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, May 10 from O'Hare Intl. to Owen Roberts Intl., returning Mon, May 13, priced at $537 found 2 days ago
American Airlines
Sat, Mar 1 - Fri, Mar 14
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$577 Roundtrip, found 10 hours ago
$577
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Mar 1 from O'Hare Intl. to Owen Roberts Intl., returning Fri, Mar 14, priced at $577 found 10 hours ago

Save more with Grand Cayman Flight + Hotel packages

VIDA Cayman

VIDA Cayman

3 out of 5
per person
Jun 7 - Jun 14
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Sprat Bay Luxury Villa

Sprat Bay Luxury Villa

4 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 14
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 7
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Ocean Paradise

Ocean Paradise

4 out of 5
per person
Jun 3 - Jun 7
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
per person
May 24 - May 29
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
The Grand Caymanian Resort

The Grand Caymanian Resort

3.5 out of 5
per person
May 24 - May 29
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
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Prices and availability subject to change. Additional terms may apply.