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East End Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hampton by Hilton Grand Cayman Seven Mile Beach

Hampton by Hilton Grand Cayman Seven Mile Beach

4 out of 5
Save 100% on your flight
Price was $1,686, price is now $1,130 per person
$1,130
per person
Feb 11 - Feb 16
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.
Cayman Luxury Rentals at One Canal Point

Cayman Luxury Rentals at One Canal Point

4 out of 5
Save 100% on your flight
Price was $3,201, price is now $1,943 per person
$1,943
per person
Feb 11 - Feb 16
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.
Cayman Luxury Rentals at The Grove

Cayman Luxury Rentals at The Grove

3.5 out of 5
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.
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
Save 100% on your flight
Price was $2,834, price is now $1,811 per person
$1,811
per person
Feb 11 - Feb 16
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.
Black Urchin

Black Urchin

4.5 out of 5
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.
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Save 100% on your flight
Price was $3,646, price is now $2,393 per person
$2,393
per person
Feb 11 - Feb 16
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.
Ocean Paradise

Ocean Paradise

4 out of 5
Save 100% on your flight
Price was $3,364, price is now $2,239 per person
$2,239
per person
Feb 11 - Feb 16
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

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
Price was $4,847, price is now $3,262 per person
$3,262
per person
Feb 11 - Feb 16
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.

East End Vacation Packages 3-4 Night Stays

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

Grand Cayman Marriott Resort

4.5 out of 5
Save 100% on your flight
Price was $1,565, price is now $1,016 per person
$1,016
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Cayman Luxury Rentals at The Grove

Cayman Luxury Rentals at The Grove

3.5 out of 5
Save 100% on your flight
Price was $1,733, price is now $1,047 per person
$1,047
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Cayman Luxury Rentals at One Canal Point

Cayman Luxury Rentals at One Canal Point

4 out of 5
Save 100% on your flight
Price was $2,046, price is now $1,245 per person
$1,245
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Save 100% on your flight
Price was $2,190, price is now $1,433 per person
$1,433
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)

East End Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Cayman Luxury Rentals at The Grove

Cayman Luxury Rentals at The Grove

3.5 out of 5
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)
Cayman Luxury Rentals at One Canal Point

Cayman Luxury Rentals at One Canal Point

4 out of 5
Save 100% on your flight
Price was $3,201, price is now $1,943 per person
$1,943
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
Save 100% on your flight
Price was $2,834, price is now $1,811 per person
$1,811
per person
Feb 11 - Feb 16
found 1 day ago
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
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)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
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
Select American Airlines flight, departing Mon, Feb 2 from John F. Kennedy Intl. to Owen Roberts Intl., returning Sat, Feb 7, priced at $270 found 6 days ago
United
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
Select United flight, departing Tue, Feb 3 from Philadelphia Intl. to Owen Roberts Intl., returning Thu, Feb 12, priced at $279 found 6 days ago
American Airlines
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
Select American Airlines flight, departing Mon, Apr 20 from Newark Liberty Intl. Airport to Owen Roberts Intl., returning Fri, Apr 24, priced at $329 found 1 day ago
United
Wed, Dec 31 - Thu, Jan 8
LGA
LaGuardia
GCM
Owen Roberts Intl.
$377 Roundtrip, found 6 days ago
$377
Roundtrip
found 6 days ago
Select United flight, departing Wed, Dec 31 from LaGuardia to Owen Roberts Intl., returning Thu, Jan 8, priced at $377 found 6 days ago