Culture matters to 21st century cities. The “creative economy” of the combined commercial, nonprofit, and informal arts is now recognized as an important economic driver that can spur the development of cities and regions, not only in downtown areas but within and across diverse local neighborhoods (Florida 2002, Glaeser 2011). A vibrant cultural life within city neighborhoods can also foster social inclusion and neighborhood well-being (Stern & Seifert 2008), increase civic engagement (Goldbard 2006), and create authentic, energetic cultural scenes in which people want to live and work (Silver 2011). In short, cultural vitality is integral to both the economic and the social well-being of cities. But what makes a city a culturally vital one? Recent research shows that successful creative communities depend on sustainable, localized networks of firms and creative workers and artists, which work together to allow the exchange of ideas and drive creativity and innovation (Scott 2006, Currid 2007). This means that effective cultural planning is increasingly local and decentralized, embracing bottom-up planning at the neighborhood or community level, while at the same time focused on developing multiple connections between the diverse organizations, people and places that make up the for-profit, non-profit and informal cultural sectors (Markusen & Gadwa 2010, Wyszomirski 2008). In line with these scholarly insights, and as part of Chicago’s 2012 cultural planning process, we have focused our collective research on identifying cultural planning best practices – at the level of principles, initiatives, projects, and events – that will encourage the development of a creative economy in Chicago that is at once place-based, connected, diverse and vital.