Much research has been conducted to improve sludge dewaterability and reveal its dewatering process. However, to date, two key issues remain unsolved: (1) the difficulty of dewatering sludge and (2) why suitable chemical conditioning can improve sludge dewaterability. This study is focused on addressing these two problems using a rheological analysis. Flow and dynamic measurements were performed to investigate the rheological properties of three types of sludge samples (raw sludge, acid-conditioned sludge, and Fenton-conditioned sludge) with different dewatering performances and a total solid content (TS) range of 20−62 g/L (2−6.2 wt %). The measured data were fitted to predict the rheological behaviors of the sludge at moderate and high TS values (15−50 wt %). A horizontal analysis and comparison of the rheological characteristics of the sludge samples indicated that rheological properties of the sludge exhibited a strong dependence on the solids content of the raw and treated sludge. An increase in the solids content significantly strengthened the solid-like properties and increased the deformation resistance, causing the sludge to become more resistant to flow and resulting in lower flowability of the sludge system; this provided an explanation for the difficulty in sludge dewatering. A vertical comparison and analysis of the rheological behavior of the sludge samples addressed the second key issue and indicated that a suitable conditioning method such as acid and Fenton oxidation conditioning had positive effects on the evolution of the rheological parameters of the sludge; namely, the conditioning resulted in weaker viscoelastic properties and better flowability. These results provide insights into the fundamental mechanism of sludge dewatering through rheological analysis.