The 43-year-old actress and her boyfriend got on the same aircraft in Switzerland along with Clooney and his 33-year-old wrestler girlfriend Keibler, reported Us magazine.
It is not known where their destination was however it marks significant progress in the friendship of screen stars Aniston and Clooney.
"The Ides of March" star is famously close to Aniston's ex-husband Pitt and therefore Clooney has not been spotted out with Aniston for several years.
The get together comes after Clooney and Pitt enjoyed dinner and drinks together at an Italian restaurant in Berkshire, England.
