The fast growth of digital health systems has led to a need to better comprehend how they interpret and represent patient-reported symptoms. Chatbots have been used in healthcare to provide clinical support and enhance the user experience, making it possible to provide meaningful clinical patterns from text-based data through chatbots. The proposed research utilises several different natural language processing methods to study the occurrences of symptom descriptions in medicine as well as analyse the patterns that emerge through these conversations within medical bots. Through the use of the Medical Conversations to Disease Dataset which contains 960 multi-turn dialogues divided into 24 Clinical Conditions, a standardised representation of conversations between patient and bot is created for further analysis by computational means. The multi-method approach uses a variety of tools, including Latent Dirichlet Allocation (LDA) to identify latent symptom themes, K-Means to group symptom descriptions by similarity, Transformer-based Named Entity Recognition (NER) to extract medical concepts, and the Apriori algorithm to discover frequent symptom pairs. Findings from the analysis indicate a coherent structure of clinically relevant topics, moderate levels of clustering cohesiveness and several high confidence rates on the relationships between symptoms like fever headache and rash itchiness. The results support the notion that conversational medical data can be a valuable diagnostic signal for early symptom interpretation, assist in strengthening decision support and improve how users interact with tele-health technology. By demonstrating a method for converting unstructured free-flowing dialogue into actionable knowledge regarding symptoms this work provides an extensible framework to further enhance future performance, dependability and clinical utility of selecting medical chatbots.