In-service teachers’ voices must be heard in order to understand the status of technology integration in Canadian elementary schools. In this qualitative case study, two Ontario private school teachers were invited to share their experiences and perspectives about their daily instruction with Chromebook through the lens of the TPACK theoretical framework. The study’s objectives were twofold: (a) to identify participating teachers’ attitudes, perceptions, and experiences teaching with Chromebook in a convincing narrative manner; and (b) to provide recommendations concerning the use of this type of digital technology device to other teachers and educators in practice. This research study once again affirmed the advantages of using Chromebook in the elementary classrooms in across three categories: saving funds, granting stable and durable hardware, and offering seamless and continuous learning. Additionally, the study attempted to add two new benefits: using Chromebook in teaching enables educators to keep their students on task and helps educators differentiate their teaching by providing more options and accommodating students’ different learning styles and abilities. Participants in the study also found it difficult to make sure students stayed on task and were not lured by the out-of-class digital world. The study also found that a better filtering system of apps working on Chromebook can benefit students’ and teachers’ experience alike. The study concludes with a discussion and implications for future research.