Flights to Grand Cayman from Chicago - $197

Cheap Flights from Chicago to Grand Cayman (CHI-GCM)

Prices were available within the past 7 days and start at $197 for one-way flights and $429 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, May 19 - Fri, May 23

MDW

Chicago

GCM

Grand Cayman

$429 Roundtrip, found 6 days ago

$429

Roundtrip

found 6 days ago

Select Southwest Airlines flight, departing Mon, May 19 from Chicago to Grand Cayman, returning Fri, May 23, priced at $429 found 6 days ago

Mon, May 19 - Fri, May 23

MDW

Chicago

GCM

Grand Cayman

$446 Roundtrip, found 6 days ago

$446

Roundtrip

found 6 days ago

Select Southwest Airlines flight, departing Mon, May 19 from Chicago to Grand Cayman, returning Fri, May 23, priced at $446 found 6 days ago

Fri, May 16 - Sat, May 24

ORD

Chicago

GCM

Grand Cayman

$476 Roundtrip, found 5 days ago

$476

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Fri, May 16 from Chicago to Grand Cayman, returning Sat, May 24, priced at $476 found 5 days ago

Sun, Jun 8 - Thu, Jun 12

ORD

Chicago

GCM

Grand Cayman

$476 Roundtrip, found 1 day ago

$476

Roundtrip

found 1 day ago

Select Air Canada flight, departing Sun, Jun 8 from Chicago to Grand Cayman, returning Thu, Jun 12, priced at $476 found 1 day ago

Wed, Jun 4 - Mon, Jun 23

ORD

Chicago

GCM

Grand Cayman

$509 Roundtrip, found 1 day ago

$509

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jun 4 from Chicago to Grand Cayman, returning Mon, Jun 23, priced at $509 found 1 day ago

Sun, Mar 1 - Thu, Mar 5

ORD

Chicago

GCM

Grand Cayman

$610 Roundtrip, just found

$610

Roundtrip

just found

Select American Airlines flight, departing Sun, Mar 1 from Chicago to Grand Cayman, returning Thu, Mar 5, priced at $610 just found