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 $494 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
Thu, Jun 6 - Sun, Jun 9
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$494 Roundtrip, found 10 hours ago
$494
Roundtrip
found 10 hours ago
Select Air Canada flight, departing Thu, Jun 6 from O'Hare Intl. to Owen Roberts Intl., returning Sun, Jun 9, priced at $494 found 10 hours ago
JetBlue Airways
Tue, May 21 - Sat, May 25
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$532 Roundtrip, found 2 days ago
$532
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, May 21 from O'Hare Intl. to Owen Roberts Intl., returning Sat, May 25, priced at $532 found 2 days ago
American Airlines
Wed, Oct 16 - Tue, Oct 22
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$575 Roundtrip, found 3 days ago
$575
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Oct 16 from O'Hare Intl. to Owen Roberts Intl., returning Tue, Oct 22, priced at $575 found 3 days ago

Save more with Grand Cayman Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Sprat Bay Luxury Villa

Sprat Bay Luxury Villa

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 2
Roundtrip non-stop flight included
Chicago (MDW) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 10
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Ocean Paradise

Ocean Paradise

4 out of 5
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
ONE Canal Point

ONE Canal Point

3.5 out of 5
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
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