WindyGrid is a real-time situational awareness platform that allows Chicago to break-down data silos and view activity in their city in street operations, licensing, and public safety. Recently launched as an open source project which can be adopted by others for internal operations or improvements to open data portals. Initial versions of WindyGrid in the spring of 2012 only existed as a complicated database that combined a handful of data sources: 911 calls, crimes, and bus locations. Later iterations grew the number of data sources, but was not usable beyond trained database administrators. Ahead of hosting a NATO conference that would require significant work from dozens of city agencies, the City of Chicago developed a user-friendly, map-based interface. For less than $100,000, the city was able to develop an application that allowed for a central query of public safety, licensing, transportation, social media, and weather data. Equivalent systems sold by large vendors are typically much more expensive and longer implementation cycles that the city likely could not afford or install ahead of the NATO summit. In the spring of 2013, the city rolled-out WindyGrid to other departments and continued to make improvements to the application. More departments used WindyGrid to aid in their operations, extending beyond the original scope around public safety. In turn, the city implemented new feature requests to help these teams. In 2015, the City created WindyGrid 2.0--a significant rewrite that was entirely comprised of open source solutions and introduced compatibility with mobile phones and tablets. At the same time, the City launched OpenGrid, which is the open source core that drives WindyGrid. Whereas WindyGrid is used internally, OpenGrid is open source and can be adopted by other cities and used for situational awareness. OpenGrid was also designed to be compatible with the rising number of open data portals. Whereas WindyGrid focused on internal city operations, OpenGrid provides the same ability to explore data for the public. The OpenGrid platform is free, whether used for internal situational awareness or navigating open data.