Liver cancer is one of the most common liver malignancies worldwide. Thermal ablation has been recognized as a promising method for its treatment, with a significant impact on clinical practice. However, the treatment’s effectiveness is heavily dependent on the experience of the clinician and would improve if paired with an image-guidance device for treatment monitoring. Conventional imaging modalities, such as computed tomography, ultrasound, and magnetic resonance imaging, show some disadvantages, motivating interest in alternative technologies. In this framework, microwave imaging was recently proposed as a potential candidate, being capable of implementing real-time monitoring by means of low-cost and portable devices. In this work, the in silico assessment of a microwave imaging device specifically designed for liver ablation monitoring is presented. To this end, an imaging experiment involving eight Vivaldi antennas in an array configuration and a practically realizable liver phantom mimicking the evolving treatment was simulated. In particular, since the actual phantom will be realized by 3D printing technology, the effect of the plastic shells containing tissues mimicking materials was investigated and discussed. The outcomes of this study confirm that the presence of printing materials does not impair the significance of the experiments and that the designed device is capable of providing 3D images of the ablated region conveying information on its extent and evolution. Moreover, the observed results suggest possible improvements to the system, paving the way for the next stage in which the device will be implemented and experimentally assessed in the same conditions as those simulated in this study.