Cheap flights from Chicago (CHI) to Grand Cayman (GCM)

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Lowest round trip fares by airline from Chicago and Grand Cayman

Cheapest prices ($166 One Way, $415 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Jan 10 - Sat, Jan 18
ORD
Chicago
GCM
Grand Cayman
$415 Roundtrip, found 5 days ago
$415
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Jan 10 from Chicago to Grand Cayman, returning Sat, Jan 18, priced at $415 found 5 days ago
Sat, Jan 11 - Sat, Jan 18
ORD
Chicago
GCM
Grand Cayman
$429 Roundtrip, found 5 days ago
$429
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Jan 11 from Chicago to Grand Cayman, returning Sat, Jan 18, priced at $429 found 5 days ago
Sat, Jan 11 - Sat, Jan 18
ORD
Chicago
GCM
Grand Cayman
$434 Roundtrip, found 5 days ago
$434
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Jan 11 from Chicago to Grand Cayman, returning Sat, Jan 18, priced at $434 found 5 days ago
Thu, Jan 9 - Sat, Jan 18
ORD
Chicago
GCM
Grand Cayman
$435 Roundtrip, found 5 days ago
$435
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Jan 9 from Chicago to Grand Cayman, returning Sat, Jan 18, priced at $435 found 5 days ago
Sun, Jan 12 - Sat, Jan 18
ORD
Chicago
GCM
Grand Cayman
$445 Roundtrip, found 5 days ago
$445
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Jan 12 from Chicago to Grand Cayman, returning Sat, Jan 18, priced at $445 found 5 days ago

Great Deals On Cheap Hotels in Grand Cayman

Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
1465 Esterley Tibbetts, Seven Mile Beach, Grand Cayman
The price is $406 per night from Dec 13 to Dec 14
$406
includes taxes & fees
$363 per night
Dec 13 - Dec 14
Stay at this 4-star beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
8.8/10 Excellent! (1,002 reviews)
"The amenities at the Westin are worth it. The grill on site is phenomenal. The rooms smell very musty though.."

Reviewed on Nov 13, 2024

Sunshine Suites Resort
Kimpton Seafire Resort + Spa, an IHG Hotel

Kimpton Seafire Resort + Spa, an IHG Hotel

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
The price is $835 per night from Dec 15 to Dec 16
$835
includes taxes & fees
$756 per night
Dec 15 - Dec 16
Stay at this 5-star 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 ...
9.8/10 Exceptional! (753 reviews)
"Property is exceptionally well maintained and staff is fantastic . Everyone more than accommodating and Christian at guest services is well accomplished at what he does and helped make our trip great."

Reviewed on Nov 19, 2024

Kimpton Seafire Resort + Spa, an IHG Hotel
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Seven Mile Beach, P.O. Box 30620, Seven Mile Beach, Grand Cayman
The price is $694 per night from Dec 15 to Dec 16
$694
includes taxes & fees
$629 per night
Dec 15 - Dec 16
Book a stay at this luxury resort in Seven Mile Beach. Enjoy a full-service spa, 6 restaurants, and a private beach. Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,001 reviews)
"The staff and front desk, especially Elise- are so helpful and kind. We are grateful that we got to experience these wonderful folks!"

Reviewed on Nov 18, 2024

The Westin Grand Cayman Seven Mile Beach Resort & Spa
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.

Fly From Chicago to Grand Cayman

Origin
Chicago
Destination
Grand Cayman
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Cheap flights from Chicago to Grand Cayman

The Windy City is a great place to call home, but a getaway to Grand Cayman can be an excellent way to break the chill. There are many ways to get to O'Hare International Airport (ORD) in Chicago other than your own vehicle. These include public transportation such as the train, buses or taxis. The turquoise water, extensive beaches and unique wildlife of the Grand Cayman islands are only a short four-hour flight away.

Attractions

The Grand Caymans are three small islands located in the Caribbean Sea. Stingray City is a popular location for snorkeling and aquatic wildlife viewing. The Caymans as a whole are known as the birthplace of recreational diving in the Caribbean. There are numerous beaches to relax on, the most popular being Seven Mile Beach. If you want to get out and swing your clubs the Britannia Golf Course offers an excellent experience.

Hints and Tips

Owen Roberts International Airport (GCM) will be your landing place in Grand Cayman, and from there you can take the public bus, a taxi or rent a car. This climate allows for temperatures to hover around 80 degrees, with lows in the 70s and highs in the 90s. You will need your U.S. passport on hand when you arrive.

Flights from Cities near Chicago

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.