Prickly sow thistle, Sonchus asper (L.) Hill, and common sow thistle, Sonchus oleraceus L., are noxious weeds. Probably originating from the Mediterranean region, they have become widespread species. They share similar morphology and are closely related. However, they differ in their chromosome numbers and the precise relationship between them remains uncertain. Understanding their chloroplast genome structure and evolution is an important initial step toward determining their phylogenetic relationships and analyzing accelerating plant invasion processes on a global scale. We assembled four accessions of chloroplast genomes (two S. asper and two S. oleraceus) by the next generation sequencing approach and conducted comparative genomic analyses. All the chloroplast genomes were highly conserved. Their sizes ranged from 151,808 to 151,849 bp, containing 130 genes including 87 coding genes, 6 rRNA genes, and 37 tRNA genes. Phylogenetic analysis based on the whole chloroplast genome sequences showed that S. asper shares a recent common ancestor with S. oleraceus and suggested its likely involvement in a possible amphidiploid origin of S. oleraceus. In total, 79 simple sequence repeats and highly variable regions were identified as the potential chloroplast markers to determine genetic variation and colonization patterns of Sonchus species.