This paper investigates skyscraper competition between New York City and Chicago. The urban economics literature is generally silent on strategic interaction between cities, yet skyscraper rivalry between these cities is a part of U.S. historiography. This paper tests whether there is, in fact, strategic interaction across cities. First, I find that each city has positive reaction functions with respect to the other city, suggesting strategic complementarity. In regard to zoning, I find that height regulations negatively impacted each city, but produced positive responses by the other city, providing evidence for strategic substitutability.