Congestive Heart Failure (CHF) is a serious chronic condition often leading to 50% mortality within 5 years. Improper treatment and post-discharge care of CHF patients leads to repeat frequent hospitalizations (i.e., readmissions). Accurately predicting patient's risk-of-readmission enables care-providers to plan resources, perform factor analysis, and improve patient quality of life. In this paper, we describe a supervised learning framework, Dynamic Hierarchical Classification (DHC) for patient's risk-of-readmission prediction. Learning the hierarchy of classifiers is often the most challenging component of such classification schemes. The novelty of our approach is to algorithmically generate various layers and combine them to predict overall 30-day risk-of-readmission. While the components of DHC are generic, in this work, we focus on congestive heart failure (CHF), a pressing chronic condition. Since healthcare data is diverse and rich and each source and feature-subset provides different insights into a complex problem, our DHC based prediction approach intelligently leverages each source and feature-subset to optimize different objectives (such as, Recall or AUC) for CHF risk-of-readmission. DHC's algorithmic layering capability is trained and tested over two real world datasets and is currently integrated into the clinical decision support tools at MultiCare Health System (MHS), a major provider of healthcare services in the northwestern US. It is integrated into a QlikView App (with EMR integration planned for Q2) and currently scores patients everyday, helping to mitigate readmissions and improve quality of care, leading to healthier outcomes and cost savings.