Skydiving may signify taking a leap of faith where you have to free-fall for a while and trust that you will have a gentle landing. Falling out of a plane without a parachute may mention that you are about to have a crash landing because of your lofty ideas or too-high ideals. Dreaming of skydiving may also tell you to get back on the ground quickly and be more realistic.... Ariadne's Book of Dream
A pleasurable dream of skydiving - floating down gently in a parachute - signifies that you have protection and security during a time in which turmoil surrounds you.
If you dream that your parachute doesn’t open, or if you are scared in the dream, this represents your feeling that you’ve been deserted by someone who was supposed to stand by you.... My Dream Interpretation