Dunning wasn’t always the tranquil middle-class neighborhood it is today—in fact, the dark history of this area kept people from settling here for many years. Underbelly tales of insanity and intrigue make up the rich and storied history of a neighborhood that nearly wasn’t.

Back in 1851, an isolated stretch of prairie just northwest of Chicago seemed like the ideal location to build a much-needed mental asylum and almshouse. Cook County purchased 160 acres of land from Peter Ludby, a local farmer who managed to nab the land by squatter’s rights back in 1839. The almshouse grounds (a politically correct term for this is "poor farm") was home to many families who spent their time growing vegetables, washing clothing, and attending the school built on the premises. By 1870, the county constructed a separate building that would house the insane asylum—it was brick, three stories high, and the cost to build it totaled around $25,000. About a decade later the institution started to admit patients suffering from tuberculosis. The disease was widespread and soon more space was needed, so in the 1880s two more buildings were added.

After the Civil War, Andrew Dunning bought 120 acres situated just south of the asylum. Dunning intended to use the land to plant a nursery and establish the foundations necessary for a village. At the time, the transportation between the area and the city of Chicago was very poor, which was a deal breaker for many would-be settlers. Those that didn’t mind the lack of transport did mind the enormous mental asylum located in such close proximity. Needless to say, Dunning had a difficult time finding people to join his village.

Eventually, a three-mile stretch of rail track was laid to connect the psychiatric facilities to the city, and the line—warily dubbed the 'crazy train' by contemporaries—provided the infrastructure needed for Dunning to recruit his settlers. As circumstance would have it, the local station built to serve the area took Dunning’s name, and soon enough the hospital itself was commonly referred to as Dunning Hospital. This didn’t sit well with potential inhabitants of the new village, and by the 1880s, the small settlement remained sparsely populated.

Dunning had failed to build his dream community in the shadow of the looming asylum, and so in 1886 he decided to sell off some of his land to groups of immigrant families interested in burial plots. Sixty-five acres went to the Scandinavian Lutheran Cemetery Association, and was later called Mount Olive Cemetery. Forty more acres went to local Jewish families for traditional burials. The entire area—from asylum to grave—was plagued with an impenetrable air of gloominess, but by 1900 a man named Henry Kolze inherited a small tavern and some wooded acreage just between the hospital and the cemeteries. Determined to fight the dreariness of the region, Kolze turned his new land into a picnic grove, and refurbished the tavern into an inn. He called his brainchild the Kolze Electric Grove and for the first time, visitors began to realize how beautiful this northwest side setting was. Of course, Kolze’s business model added to the appeal; plenty of dancing space, a nightly orchestra, strings of gas lanterns, and nickel-beers made the area a desirable destination. As Chicagoans were making the trek to chill at the Grove, the corruption, misconduct, and criminal conditions of the nearby asylum were becoming apparent to government officials.

After a series of official investigations, the poor farm was relocated to Oak Forest in 1910, and just two years later the state of Illinois bought the hospital and property from the county for one dollar. The name was changed simply to Chicago State Hospital, but everyone still called it Dunning. At the time, the hospital’s population still dwarfed that of the neighborhood that surrounded it, but following World War I, an influx of Swedish, German, and Polish immigrants began to fill the neighborhood. In 1934, Wright Junior College was built nearby, which resulted in a large population of students and recent graduates. As for the State Hospital, that looming beast that had been a blight on the area for so long, fell into drastic disrepair. It was razed during the 1970s and replaced by the respectable Chicago-Read Mental Health Center.