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Lowest round trip fares by airline from Chicago and Grand Cayman

Cheapest prices ($190 One Way, $435 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 12 - Thu, Oct 17
ORD
Chicago
GCM
George Town
$435 Roundtrip, found 1 day ago
$435
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Oct 12 from Chicago to George Town, returning Thu, Oct 17, priced at $435 found 1 day ago
Wed, Sep 18 - Sun, Sep 22
ORD
Chicago
GCM
George Town
$480 Roundtrip, found 2 days ago
$480
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed, Sep 18 from Chicago to George Town, returning Sun, Sep 22, priced at $480 found 2 days ago
Tue, Sep 17 - Sun, Sep 22
ORD
Chicago
GCM
George Town
$540 Roundtrip, found 2 days ago
$540
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Sep 17 from Chicago to George Town, returning Sun, Sep 22, priced at $540 found 2 days ago
Tue, Sep 17 - Tue, Sep 24
ORD
Chicago
GCM
George Town
$575 Roundtrip, found 2 days ago
$575
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 17 from Chicago to George Town, returning Tue, Sep 24, priced at $575 found 2 days ago
Tue, Sep 17 - Tue, Sep 24
ORD
Chicago
GCM
George Town
$577 Roundtrip, found 2 days ago
$577
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 17 from Chicago to George Town, returning Tue, Sep 24, priced at $577 found 2 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 15 to May 16
$255
per night
May 15 - May 16
Stay at this 4-star beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the pool and ...
8.8/10 Excellent! (1,006 reviews)
Great place to stay
"The best value stay in Grand Cayman with low prices, great service, and exceptional accessibility to Seven Mile Beach. Britney and Ella were outstanding."

Reviewed on May 12, 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 27 to May 28
$849
per night
May 27 - May 28
Stay at this 5-star luxury hotel in Seven Mile Beach. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the ...
9.8/10 Exceptional! (689 reviews)
"We stayed 4 nights here at Kimpton Seafire and it was even an understatement to say it was phenomenal. The facility itself almost looks newly built because it is well maintained. Staff are all kind and attentive. The garden around the pool is full of shrubs, flowers, and coconut trees all of which ..."

Reviewed on May 12, 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
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 pool and the helpful ...
8.6/10 Excellent! (1,004 reviews)
"Front lobby furniture, especially sectional couch, needs to be replaced as well as other furniture."

Reviewed on May 13, 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

Other Flights to Grand Cayman

Other Flights from Chicago

*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.