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Grand Cayman Vacation Packages

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Grand Cayman
Cayman Islands
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Grand Cayman Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Wyndham Reef Resort Grand Cayman

3.5 out of 5

Price was $1,096, price is now $767 per person

$767

per person

May 4 - May 7

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to George Town (GCM)

Book a stay at this beach resort in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Colliers Public Beach and Barefoot Beach are located nearby.

Kimpton Seafire Resort + Spa by IHG

5 out of 5

Save 100% on your flight

Price was $4,388, price is now $2,766 per person

$2,766

per person

May 4 - May 7

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to George Town (GCM)

Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5

Price was $3,366, price is now $2,137 per person

$2,137

per person

Mar 24 - Mar 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) to George Town (GCM)

Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

Hotel Indigo Grand Cayman by IHG

4.5 out of 5

Price was $1,265, price is now $838 per person

$838

per person

May 4 - May 7

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) 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.

Ocean Paradise

4 out of 5

Save 100% on your flight

Price was $1,949, price is now $1,396 per person

$1,396

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) 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.

Shangri-La Boutique Bed & Breakfast

4 out of 5

Price was $1,716, price is now $1,233 per person

$1,233

per person

Mar 24 - Mar 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) to George Town (GCM)

Stay at this hotel in West Bay. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

Lighthouse Point Residences

3.5 out of 5

Save 100% on your flight

Price was $1,576, price is now $1,142 per person

$1,142

per person

May 4 - May 7

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to George Town (GCM)

Stay at this condo in West Bay. Enjoy free WiFi, free parking, and furnished balconies. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

Club Suites at Rum Point

4 out of 5

Price was $3,795, price is now $2,811 per person

$2,811

per person

Mar 24 - Mar 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.