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Sister Islands Vacation Packages

Build your package with 2 more options

Sister Islands Flight + Hotel Packages

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

Conch Club Cottage

2 out of 5
Price was $1,634, price is now $1,257 per person
$1,257
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Little Cayman (LYB)
Book a stay at this beach hotel in Little Cayman. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions South Hold Sound and Booby Pond Nature Reserve are located nearby.
Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was $1,692, price is now $1,320 per person
$1,320
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to West End (CYB)
Stay at this hotel in West End. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cayman Brac Beaches and Cio's Craig (Wilderness Wall) are located nearby.

Sister Islands Vacation Packages 3-4 Night Stays

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

Conch Club Cottage

2 out of 5
Price was $1,634, price is now $1,257 per person
$1,257
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Little Cayman (LYB)
Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was $1,692, price is now $1,320 per person
$1,320
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to West End (CYB)

Sister Islands Vacation Packages 5-7 Night Stays

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

Conch Club Cottage

2 out of 5
Save 100% on your flight
Price was $1,640, price is now $1,247 per person
$1,247
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Little Cayman (LYB)
Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Save 100% on your flight
Price was $1,597, price is now $1,263 per person
$1,263
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to West End (CYB)

Top Flight Deals

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

Cayman Airways
Mon, Jun 15 - Wed, Jun 17
JFK
John F. Kennedy Intl.
LYB
Edward Bodden Airfield
$591 Roundtrip, found 1 hour ago
$591
Roundtrip
found 1 hour ago
Select Cayman Airways flight, departing Mon, Jun 15 from John F. Kennedy Intl. to Edward Bodden Airfield, returning Wed, Jun 17, priced at $591 found 1 hour ago
Cayman Airways
Mon, Jun 15 - Wed, Jun 24
JFK
John F. Kennedy Intl.
LYB
Edward Bodden Airfield
$626 Roundtrip, found 3 hours ago
$626
Roundtrip
found 3 hours ago
Select Cayman Airways flight, departing Mon, Jun 15 from John F. Kennedy Intl. to Edward Bodden Airfield, returning Wed, Jun 24, priced at $626 found 3 hours ago
Cayman Airways
Mon, Jun 15 - Tue, Jun 16
JFK
John F. Kennedy Intl.
LYB
Edward Bodden Airfield
$627 Roundtrip, found 1 hour ago
$627
Roundtrip
found 1 hour ago
Select Cayman Airways flight, departing Mon, Jun 15 from John F. Kennedy Intl. to Edward Bodden Airfield, returning Tue, Jun 16, priced at $627 found 1 hour ago
Cayman Airways
Thu, Jun 18 - Wed, Jun 24
JFK
John F. Kennedy Intl.
LYB
Edward Bodden Airfield
$661 Roundtrip, found 3 hours ago
$661
Roundtrip
found 3 hours ago
Select Cayman Airways flight, departing Thu, Jun 18 from John F. Kennedy Intl. to Edward Bodden Airfield, returning Wed, Jun 24, priced at $661 found 3 hours ago