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To fly, you need to be a skilled martial artist who can control their ki. Bulma is not a martial artist and Chi Chi can't control her ki.
In episode 288 of Dragonball Z
caus he likes to get tickled by chi chi or bulma.
Chi-Chi, who is the daughter of the ox king. They meet early in the series when Goku was 14 when him and Bulma were trying to get the dragon balls.