Search Deals onWest Bay Vacation Packages
West Bay Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Cayman Luxury Rentals at The Grove
Save 100% on your flight
Price was $1,972, price is now $1,260 per person
$1,260
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this apartment in Seven Mile Beach. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Cayman Luxury Rentals at One Canal Point
Save 100% on your flight
Price was $2,933, price is now $1,810 per person
$1,810
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this villa in Seven Mile Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Hampton by Hilton Grand Cayman Seven Mile Beach
Save 100% on your flight
Price was $2,141, price is now $1,364 per person
$1,364
per person
Feb 11 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this resort in Seven Mile Beach. Enjoy free breakfast, free parking, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
Hotel Indigo Grand Cayman by IHG
Save 100% on your flight
Price was $4,857, price is now $3,115 per person
$3,115
per person
Feb 11 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Black Urchin
Save 100% on your flight
Price was $14,121, price is now $9,219 per person
$9,219
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Book a stay at this luxury hotel in Bodden Town. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Boddentown Art Shop and Mission House are located nearby.
Grand Cayman Marriott Resort
Save 100% on your flight
Price was $3,593, price is now $2,347 per person
$2,347
per person
Feb 11 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
Ocean Paradise
Save 100% on your flight
Price was $4,345, price is now $2,861 per person
$2,861
per person
Feb 11 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, free parking, and a garden. Popular attractions Cayman Kai Public Beach and Star Fish Point are located nearby.
Club Suites at Rum Point
Save 100% on your flight
Price was $6,282, price is now $4,316 per person
$4,316
per person
Feb 11 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Book a stay at this beach hotel in North Side. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Rum Point Beach and Cayman Kai Public Beach are located nearby.
West Bay Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
West Bay Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Feb 2 - Sat, Feb 7
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$270 Roundtrip, found 6 days ago
$270
Roundtrip
found 6 days ago
Tue, Feb 3 - Thu, Feb 12
PHL
Philadelphia Intl.
GCM
Owen Roberts Intl.
$279 Roundtrip, found 6 days ago
$279
Roundtrip
found 6 days ago
Mon, Apr 20 - Fri, Apr 24
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Wed, Dec 31 - Thu, Jan 8
LGA
LaGuardia
GCM
Owen Roberts Intl.
$377 Roundtrip, found 6 days ago
$377
Roundtrip
found 6 days ago
Discover Other Travel Deals
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
