Mathematics, being a very ancient discipline, is usually seen as a formal subject that must be learned for school purposes, which is very far from creativity and fun. Also, mathematical skills are often considered a talent, so students are easily divided into gifted and not gifted, with a focus on speed and accuracy rather than encouraging the process of juggling between divergent and convergent thinking. In the present paper, we aimed at investigating the relationship between mathematical reasoning and different aspects of creative thinking, such as divergent and convergent creativity, aesthetic appreciation, and humor. To do so, 146 second and third graders in a primary school in Milan have been recruited and tested with mathematical and creative tasks. Correlational analyses showed significant positive relations between flexibility and originality dimensions of creativity and mathematical performance. Results are discussed by providing a theoretical framework about the relation between mathematics and creative skills.