Cayman Islands Luxury Holidays
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Photo by Cayman Islands Department of Tourism
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Price found within the past 48 hours. Click for updated prices.
Sunshine Suites Resort
Price was €1,893, price is now €1,540 per person
€1,540
per person
12 Feb - 17 Feb
found 1 day ago
Return flight included
Chicago (ORD) to George Town (GCM)
9/10 Wonderful! (1,001 reviews)
Loved the hotel! Great location and it was nice to be able to enjoy all of the Westins amenities. The staff at The Sunshine Hotel and the Westin were amazing.
Reviewed on 10 Jan 2026
The Ritz-Carlton, Grand Cayman
Save 100% on your flight
Price was €9,156, price is now €7,613 per person
€7,613
per person
12 Feb - 17 Feb
found 1 day ago
Return flight included
Chicago (ORD) to George Town (GCM)
9.6/10 Exceptional! (1,004 reviews)
Arrival was unpleasant because their system did not reflect my reservation correctly.
It took Expedia’s intervention to correct it and force them to honor it.
The room was in good condition. However, de Air conditioner did work correctly.
The property and staff are good.
But, access to the beach area is across the street.
A Long walk every time you want to go to the beach.
Reviewed on 11 Jan 2026
Grand Cayman Marriott Resort
Price was €2,308, price is now €1,929 per person
€1,929
per person
12 Feb - 17 Feb
found 1 day ago
Return flight included
Chicago (ORD) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
Breakfast menu was fresh and ocean view from the room was excellent. Really enjoyed the accommodations.
Reviewed on 12 Jan 2026
Kimpton Seafire Resort + Spa by IHG
Price was €4,444, price is now €3,937 per person
€3,937
per person
12 Feb - 17 Feb
found 1 day ago
Return flight included
Chicago (ORD) to George Town (GCM)
9.8/10 Exceptional! (953 reviews)
clean, staff are amazing food is great and the beach is out of this world.
Reviewed on 9 Jan 2026
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was €3,813, price is now €3,566 per person
€3,566
per person
12 Feb - 17 Feb
found 1 day ago
Return flight included
Chicago (ORD) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
Great service and amenities with clean beach! Rooms areas are older, but hotel makes up for it with great value!
Reviewed on 13 Jan 2026
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View all tripsPrice found within the past 48 hours. Click for updated prices.
Kimpton Seafire Resort + Spa by IHG
Price was €4,444, price is now €3,937 per person
€3,937
per person
12 Feb - 17 Feb
found 1 day ago
Return flight included
Chicago (ORD) to George Town (GCM)
9.8/10 Exceptional! (953 reviews)
clean, staff are amazing food is great and the beach is out of this world.
Reviewed on 9 Jan 2026
The Ritz-Carlton, Grand Cayman
Save 100% on your flight
Price was €9,156, price is now €7,613 per person
€7,613
per person
12 Feb - 17 Feb
found 1 day ago
Return flight included
Chicago (ORD) to George Town (GCM)
9.6/10 Exceptional! (1,004 reviews)
Arrival was unpleasant because their system did not reflect my reservation correctly.
It took Expedia’s intervention to correct it and force them to honor it.
The room was in good condition. However, de Air conditioner did work correctly.
The property and staff are good.
But, access to the beach area is across the street.
A Long walk every time you want to go to the beach.
Reviewed on 11 Jan 2026
Don't see what you're looking for?
See all available trips from Chicago to Cayman Islands
View all trips
The Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
The price is €1,129 per night from 19 Jan to 20 Jan
€1,129
19 Jan - 20 Jan
includes taxes & fees
Stay at this luxury resort in Seven Mile Beach. Enjoy free Wi-Fi, free valet parking and 2 outdoor pools. Our guests praise the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,002 reviews)
Everything is amazing. Service, staff, food…
Reviewed on 30 Dec 2025
Caribbean Club Luxury Condo Hotel
871 West Bay Road Seven Mile Beach Grand Cayman
Stay at this luxury aparthotel in Seven Mile Beach. Enjoy free Wi-Fi, a beach locale and room service. Popular attractions Seven Mile Beach and Port of Georgetown ...
Excellent Property. Their front desk team needs some working on because they give couldn't care less attitude.
Reviewed on 25 Feb 2024
Le Soleil d'Or
2147 South Side Road West End Cayman Brac
Stay at this luxury hotel in West End. Enjoy private pools, a private beach and a free beach shuttle. Popular attractions MV Captain Keith Tibbetts Shipwreck ...
Fantastic Property
Staff were unreal and the cottage was amazing
Reviewed on 24 Jul 2019
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
