As the world becomes more interconnected, educators are faced with opportunities to collaborate across cultures. Using the theory of educational cosmopolitanism (Wahlström, 2014) and the pedagogy of collaborative inquiry, this collective case study explores how Chinese and Americans teachers perceive the assets and challenges of conducting collaborative inquiry with their students across cultures, and how they collaboratively plan in order to conduct these inquiries. Results demonstrated both assets (i.e., promotion of global citizenship and college and career preparation) and challenges (i.e., time, digital access, and the need for sustainable external support). The results are significant because they sheds light on how educational cosmopolitanism holds promise for meeting challenges of conducting collaborative inquiry with culturally and geographically diverse teachers.