First Airmail stamp in ChilePrivate issue made by aviator Clodomiro Figueroa P.
He made a first experimental airmail flight Santiago-Valparaíso (and vice versa) and first experimental international airmail flight Santiago - Mendoza (Argentina).
Figueroa carried letters and Postcards and issued this stamp for this purpose :

The stamp is a photographic print on cardboard and it was produced in the Photo Studio of Aurelio Vera.
Total printing : 800 stamps
Perforated with sewing machine.
First Flight: Santiago to Valparaiso and vice versa. January 1, 1919. Airplane: Bleriot 80 Hp
539 letters in total (in both directions)
Second flight: Santiago to Mendoza (in Argentina). August 20, 1921. Airplane: Morane Saulnier Le Rhone 110 Hp
About 60 letters in total.

Arriving at Mendoza, the airplane had a motor failure, so he was unable to perform the return flight and had to return across the Andes (mountains) by train.
In 1988 was issued a stamp commemorating the first flight of 1919:

The image show the Bleriot 80 Hp airplane flying over Valparaiso