The gap between the planet and its rings "is a region no spacecraft has ever explored," NASA said, on a web page of milestones about what it called Cassini's 'First Grand Finale Dive'.
The orbiter was set to use its antenna, shaped like a disc, as a shield to deflect ring particles during the manoeuvre, which would render the spaceship unreachable while its instruments would remain on, the agency said.
The first dive is part of Cassini's grand finale, which NASA says is a six-month "daring" set of orbits it likened to a whole new mission, including 22 weekly dives between Saturn and its rings.
Cassini, launched in 1997, has been orbiting Saturn since 2004, providing data about the planet and its moons and is scheduled to make a last plunge into the planet in September, ending its mission.
Earlier this month, NASA said Cassini had captured evidence of the ingredients needed to support life on Saturn's moon Enceladus.