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 ($205 One Way, $568 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, May 25 - Sat, Jun 1
ORD
Chicago
GCM
George Town
$568 Roundtrip, found 6 days ago
$568
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, May 25 from Chicago to George Town, returning Sat, Jun 1, priced at $568 found 6 days ago
Wed, Mar 5 - Fri, Mar 14
ORD
Chicago
GCM
George Town
$577 Roundtrip, found 4 days ago
$577
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Mar 5 from Chicago to George Town, returning Fri, Mar 14, priced at $577 found 4 days ago
Wed, Mar 5 - Fri, Mar 14
ORD
Chicago
GCM
George Town
$578 Roundtrip, found 4 days ago
$578
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Mar 5 from Chicago to George Town, returning Fri, Mar 14, priced at $578 found 4 days ago
Wed, Mar 5 - Fri, Mar 14
ORD
Chicago
GCM
George Town
$589 Roundtrip, found 4 days ago
$589
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Mar 5 from Chicago to George Town, returning Fri, Mar 14, priced at $589 found 4 days ago
Fri, Mar 7 - Wed, Mar 12
ORD
Chicago
GCM
George Town
$599 Roundtrip, found 6 days ago
$599
Roundtrip
found 6 days ago
Select United flight, departing Fri, Mar 7 from Chicago to George Town, returning Wed, Mar 12, priced at $599 found 6 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 $255 per night from May 3 to May 4
$255
per night
May 3 - May 4
Stay at this 4-star beach hotel in Seven Mile Beach. Enjoy breakfast, room service, and beach cabanas. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (1,004 reviews)
"Walking distance to the beach"

Reviewed on Apr 26, 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 $849 per night from May 26 to May 27
$849
per night
May 26 - May 27
Stay at this 5-star luxury hotel in Seven Mile Beach. Enjoy free parking, 4 restaurants, and a beach locale. Our guests praise the helpful staff and the clean ...
9.8/10 Exceptional! (687 reviews)
"We loved it"

Reviewed on Apr 21, 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 $689 per night from May 27 to May 28
$689
per night
May 27 - May 28
Stay at this luxury resort in Seven Mile Beach. Enjoy 6 restaurants, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (1,002 reviews)
"Property was nice and well kept with a beautiful beach front. Staff was friendly and helpful. Only downside is the beds. Double beds offered are really not large enough for 2 people to sleep in. While I know the beds come specifically advertised as doubles I wish they had a 2 queen option. In addition, ..."

Reviewed on Apr 27, 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.