In today’s world, cities experience continuous growth and transformation. Amid this progress, certain areas often remain underdeveloped in comparison to others, leading to disparities. The research evaluates infrastructural growth and development in Chicago, while focusing on a data-driven approach rather than a perspective-based approach. Open-source data available on Chicago Data portal was used to collect statistics of demographics, traffic, public amenities like farmer markets, sport facilities, art installations, etc. This data was mapped based on geographical coordinates. Each data point was assigned a rectangle, which was then scaled based on the population. To integrate a citizen’s perspective, open- source API of twitter was evaluated to understand the nature of tweets made from a certain location. Positive tweets such as ‘Happy’, ‘Safe’, etc. were indicators of development. Based on the nature of tweets, the rectangles were filtered into white, black and grey. Finally, all the rectangles were re-mapped to a larger square grid rather than a map format, to allow dissociation with any existing human inhibitions pertaining to geographical locations and analyze the obtained data neutrally. Overall, the research seeks to provide a holistic understanding of the quality of life in Chicago.