In conversational search, which aims to retrieve passages containing essential information, queries suffer from high dependency on the preceding dialogue context. Therefore, reformulating conversational queries into standalone forms is essential for the effective utilization of off-the-shelf retrievers. Previous methodologies for conversational query search frequently depend on human-annotated gold labels. However, these manually crafted queries often result in sub-optimal retrieval performance and require high collection costs. In response to these challenges, we propose Iterative Conversational Query Reformulation (IterCQR), a methodology that conducts query reformulation without relying on human oracles. IterCQR iteratively trains the QR model by directly leveraging signal from information retrieval (IR) as a reward. Our proposed IterCQR method shows state-of-the-art performance on two datasets, demonstrating its effectiveness on both sparse and dense retrievers. Notably, IterCQR exhibits robustness in domain-shift, low-resource, and topic-shift scenarios.