Chicago to Grand Cayman Flights (CHI-GCM) from $174

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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 $418 and $174 for one-way flights to Grand Cayman for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Sep 15 - Thu, Oct 3
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$418 Roundtrip, found 1 day ago
$418
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Sep 15 from O'Hare Intl. to Owen Roberts Intl., returning Thu, Oct 3, priced at $418 found 1 day ago
Air Canada
Sat, Nov 23 - Sun, Dec 1
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$435 Roundtrip, found 5 days ago
$435
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sat, Nov 23 from O'Hare Intl. to Owen Roberts Intl., returning Sun, Dec 1, priced at $435 found 5 days ago
American Airlines
Sat, Aug 17 - Sat, Aug 24
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$442 Roundtrip, found 4 hours ago
$442
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Aug 17 from O'Hare Intl. to Owen Roberts Intl., returning Sat, Aug 24, priced at $442 found 4 hours ago

Save more with Grand Cayman Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Chicago (CHI) 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)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
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
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)
Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

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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