Abstract-Co-development of design rules and layout methodologies is the key to successful adoption of a technology. In this work, we propose Chip-level Design Rule Evaluator (ChipDRE), the first framework for systematic evaluation of design rules and their interaction with layouts, performance, margins and yield at the chip scale (as opposed to standard cell-level). A "good chips per wafer" metric is used to unify area, performance, variability and yield. The framework uses a generated virtual standard-cell library coupled with a mix of physical design, semiempirical, and machine-learning-based models to estimate area and delay at the chip level. The result is a unified design-quality estimate that can be computed fast enough to allow using ChipDRE to optimize a large number of complex design rules. For instance, a study of well-to-active spacing rule reveals a non-monotone dependence of rule value to chip area (although the dependence to cell area is monotone) due to delay changes coming from well-proximity effect.