The goal of this chapter is to explore the evolving relationship between the Chicago School of Economics and libertarianism. In the post-World War Two era, the Chicago School developed a methodological stance of individualism, which made it attractive to libertarians. But that stance does not require the normative commitment to individual freedom that libertarianism does. The chapter traces the evolution of Chicago School thought from the time of Frank Knight and Jacob Viner until today, when Chicago economics is increasingly less dependent on Milton Friedman and Gary Becker, and the distance between it and libertarianism has grown.