Cayman Airways and American Airlines have round-trip flights from Chicago (ORD) to Grand Cayman (GCM) for $392-$402, NONSTOP. Flights June, July, August. Weekends available. Origin/Destination reversible.
Note: Carry-on bag and seat selection is allowed for free on Cayman Airways, but the flights are Sunday departures with Sunday returns.
Note: Carry-on bag is allowed for free on American Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.