Development in what is now known as Greater Grand Crossing began in 1853, soon after a train accident that killed 18 people and injured 40 others. The accident happened at a site where "Roswell B. Mason, who was to become a Chicago mayor, secretly had intersecting tracks built for the Illinois Central across the rail lines of the Lake Shore & Michigan Southern Railroad," resulting in a dangerous crossing for trains. Trains were forced to come to a stop before proceeding through the intersection since it was such a hazard, and because of this, developers felt that this area, as it was already served by the railroads, was the perfect place to begin building a suburban community on the southern outskirts of the city. The community was annexed into Chicago in 1889, and "the World's Columbian Exposition of 1893 further stimulated growth."
While new construction projects in the neighborhood have been few and far between in recent decades, one that has sprouted up recently is the Gary Comer Youth Center. Paid for by the founder of Lands' End, and Greater Grand Crossing native, Gary Comer, the youth center "is dedicated to providing a greater opportunity for young people in this neighborhood to practice, to learn, to study, and to sharpen their skills and intellect."