Dropping in unannounced around 11am, the 49-year-old stunned staff and members at the indoor skydiving simulation facility.
Accompanied by his wife, model Cecilia Wang and his two children, Yen tried his hand at the ride, which simulates a freefall skydive.
An iFly spokesperson told Yahoo! Singapore no one was expecting his arrival as he only made the booking online himself.
"We were quite surprised actually. The instructor said that he was really good in the flight. Usually, it takes other people 30 seconds before they can fly on their own. But for Yen, he was able to fly on his own within a few seconds," she said.
"It might have got to do with the way his body is conditioned," she added.
The spokesperson added that Yen was very "friendly" with everyone, and took at least ten to 20 photos with members of the public.Yen posed with the iFly instructors on Friday morning. (Photo courtesy of iFly Singapore)
Yen and his family subsequently went to have lunch at Skyloft, the rooftop restaurant and bar.
The action star first made his acting debut at the age of 20 and over a 28-year career in showbiz has taken on a variety of roles as actor, stuntman, martial arts choreographer and director.