This paper examines thirty major American cities to determine how "choice-friendly" they are today. Selected for their size and geographic diversity, the cities reveal both the best and worst conditions for school choice to take root and grow. "School choice" is defined broadly to incorporate a wide range of public and private options, including charter, magnet, and private schools, as well as mechanisms for accessing these options, including open enrollment, vouchers, and tax credit scholarships. Data on these options were collected from public databases and other sources, including district and state websites, newspaper articles, and education insiders in each city. The authors used these data to construct nearly fifty indicators of choice friendliness, then assessed the relative merits and drawbacks of each city's choice atmosphere relative to three areas: (1) "Political Support": measures the views of various individuals and groups as they pertain to school choice; (2) "Policy Environment": addresses topics such as the strength of state charter laws; funding and facilities access; non-profit, business, and philanthropic support; consumer supports, including report cards and transportation; and quality control mechanisms, such as policies for closing schools; and (3) "Quantity and Quality": addresses the types of school choice options that are available; the mechanisms for accessing those options, such as voucher and open enrollment programs; the portion of market share occupied by charters and other specialized schools; and the quality of the choice sector. Based on how they measured up, cities were awarded scores and ranks, overall and for each of these three areas. Notable patterns across the cities are identified that in turn informed the authors' recommendations for cities seeking to become more choice-friendly. City profiles by rank, patterns, and recommendations are detailed in this report. [Foreword by Amber M. Northern and Michael J. Petrilli. Contributors to the executive summary and sections one - six include: Julie Casper, Eric Chan, Solana Chehtman, Jane Griesinger, David Houston, and Christopher Lim. Section seven, "City Profiles by Rank," was written by David Griffith.]