Background: Inferior Vena Cava (IVC) filters have become an advantageous treatment modality for patients with venous thromboembolism. As the use of these filters continues to grow, it is imperative for providers to appropriately educate patients in a comprehensive yet understandable manner. Likewise, generative artificial intelligence models are a growing tool in patient education, but there is little understanding of the readability of these tools on IVC filters. Methods: This study aimed to determine the Flesch Reading Ease (FRE), Flesch–Kincaid, and Gunning Fog readability of IVC Filter patient educational materials generated by these artificial intelligence models. Results: The ChatGPT cohort had the highest mean Gunning Fog score at 17.76 ± 1.62 and the lowest at 11.58 ± 1.55 among the Copilot cohort. The difference between groups for Flesch Reading Ease scores (p = 8.70408 × 10⁻⁸) was found to be statistically significant albeit with priori power found to be low at 0.392. Conclusions: The results of this study indicate that the answers generated by the Microsoft Copilot cohort offers a greater degree of readability compared to ChatGPT cohort regarding IVC filters. Nevertheless, the mean Flesch–Kincaid readability for both cohorts does not meet the recommended U.S. grade reading levels.