Cheap flights from Chicago to Grand Cayman

View AU$342 flight on Wed, 18 Jun. 2025Opens in a new window

Popular airlines from Chicago to Grand Cayman

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue., 17 Jun. - Tue., 24 Jun.
MDW
Chicago
GCM
Grand Cayman
AU$941 Return, found 5 days ago
AU$941
Return
found 5 days ago
Select Delta flight, departing Tue., 17 Jun. from Chicago to Grand Cayman, returning Tue., 24 Jun., priced at AU$941 found 5 days ago
Delta
Tue., 17 Jun. - Tue., 24 Jun.
ORD
Chicago
GCM
Grand Cayman
AU$941 Return, found 5 days ago
AU$941
Return
found 5 days ago
Select Delta flight, departing Tue., 17 Jun. from Chicago to Grand Cayman, returning Tue., 24 Jun., priced at AU$941 found 5 days ago
Air Canada
Wed., 18 Jun. - Wed., 25 Jun.
ORD
Chicago
GCM
Grand Cayman
AU$956 Return, found 3 days ago
AU$956
Return
found 3 days ago
Select Air Canada flight, departing Wed., 18 Jun. from Chicago to Grand Cayman, returning Wed., 25 Jun., priced at AU$956 found 3 days ago
United
Wed., 18 Jun. - Wed., 25 Jun.
ORD
Chicago
GCM
Grand Cayman
AU$1,025 Return, found 3 days ago
AU$1,025
Return
found 3 days ago
Select United flight, departing Wed., 18 Jun. from Chicago to Grand Cayman, returning Wed., 25 Jun., priced at AU$1,025 found 3 days ago
Air Canada
Wed., 18 Jun. - Wed., 25 Jun.
ORD
Chicago
GCM
Grand Cayman
AU$1,027 Return, found 3 days ago
AU$1,027
Return
found 3 days ago
Select Air Canada flight, departing Wed., 18 Jun. from Chicago to Grand Cayman, returning Wed., 25 Jun., priced at AU$1,027 found 3 days ago
United
Thu., 19 Jun. - Thu., 26 Jun.
ORD
Chicago
GCM
Grand Cayman
AU$1,068 Return, found 1 day ago
AU$1,068
Return
found 1 day ago
Select United flight, departing Thu., 19 Jun. from Chicago to Grand Cayman, returning Thu., 26 Jun., priced at AU$1,068 found 1 day ago
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