Among the various challenges that adult and other late language learners face on their journey to achieving nativelike proficiency, chunking has been identified as one of the most difficult tasks to master. Language users are able to derive and utilize chunks during language processing—both in the first (L1) and the second language (L2)—yet the extent to which the L2 learners utilize and benefit from chunking is not on a par with L1 speakers. L2 learners are generally less sensitive to the statistical regularities in the linguistic input and possess a smaller repertoire of multiword expressions, leaving them susceptible to slower real-time language processing, hampered comprehension during conversation, and distinct production errors. Drawing on insights from Brian MacWhinney's Unified Competition Model of L1 and L2 acquisition, this review examines these unique challenges in L2 chunking as a function of differences between L1 and L2 learning. According to the Unified Competition Model, the existence of deeply entrenched L1 linguistic representations may hinder effective L2 chunking by encouraging over-segmentation in favor of L1 transference at the lexical level and diverting the necessary attention away from the grammatical elements in prefabricated multiword units. Based on these observations, we offer practical suggestions for educators to facilitate chunking in L2 learners and bring them closer to nativelike fluency.