In this chapter, we will investigate how reading comprehension skills and creativity develop in children raised in a bilingual environment. The chapter reports a case study on a small group of 17 pre-school students in Singapore that explores several dimensions of creativity and some possibly of language ability. The study hopes to identify areas for further investigation on a larger scale. Children explore the world around them from the moment they are born. The experiences are shaped by the culture they are born in. Plasticity of the children’s brain to retain experience and its ability to reproduce them ensure the passing down of culture (Vygotsky 2004). Vygotsky (2004) pointed out that if the brain merely passively reproduces previous experiences, human beings would always be looking backward. What makes human beings future oriented is the brain’s ability to combine elements into new ideas and concepts. The combinatorial ability, which is also known as imagination, is the basis for creativity. If experience is the basis of imagination, then broadening children’s experience will provide a fertile ground for imagination, and hence, creativity, to flourish (Vygotsky 2004). The more enriched children’s experiences are, the more elements they will have to operate their imagination. Reading, which allows children to explore the world vicariously, is an effective way to enrich children’s experience. When children read, they construct meaning from what they read, augmenting and enriching the representations they build from when they explore and make sense of the physical world. It allows greater opportunity for imagination and for creativity.