This research quantifies the relationship between the cost of earliness and lateness by empirically observing commute trips from two different sources. The first empirical analysis uses individual level travel survey data from six metropolitan regions while the second analysis uses traffic data from the Twin Cities freeway network. The analysis conducted in this research provides a method to estimate the ratio of the costs of earliness to lateness for different datasets. This can be a useful tool for traffic engineers and planners, to assist them in the development and implementation of improved control strategies for congested cities. The results also corroborates the hypothesis of earliness being less expensive than lateness and show that the finding holds steady over time and across different regions and levels.