Migraine is a chronic disorder with episodic attacks, and patients with a migraine often report that certain factors can trigger their headache, with chocolate being the most popular type of food-based trigger. Many studies have suggested a link between chocolate and headaches; however, the underlying physiological mechanisms are unclear. As premonitory symptoms may herald migraine attacks, a question arises regarding whether eating chocolate before a headache is a consequence of a food craving or indeed a real trigger. Here, we aim to summarize the available evidence on the relationship between chocolate and migraines. All articles concerning this topic published up to January 2020 were retrieved by searching clinical databases, including EMBASE, MEDLINE, PubMed, and Google Scholar. All types of studies have been included. Here, we identify 25 studies investigating the prevalence of chocolate as a trigger factor in migraineurs. Three provocative studies have also evaluated if chocolate can trigger migraine attacks, comparing it to a placebo. Among them, in 23 studies, chocolate was found to be a migraine trigger in a small percentage of participants (ranging from 1.3 to 33), while all provocative studies have failed to find significant differences between migraine attacks induced by eating chocolate and a placebo. Overall, based on our review of the current literature, there is insufficient evidence that chocolate is a migraine trigger; thus, doctors should not make implicit recommendations to migraine patients to avoid it.