Settlement in the neighborhood began in the 1830s, when a saloon was opened for truck farmers carrying produce to the city by George Merrill. His saloon was opened in his home which was the first business in the area and was located at Armitage and Grand.

The area was originally land bought by William Sayre in what was then Jefferson Township through a land sale. By the 1870s, the area saw the extension of the railroad into the area, and the development of housing naming the area after Montclare, New Jersey.

Dunning is named after Andrew Dunning, who bought land for a nursery after the Civil War. The neighborhood was still a remote area in the prairie when, in 1851, it was selected by Cook County to be the location of a poor farm and an asylum for the insane.

Irving Park was originally planned as farm land, when four men decided to expand the area and to transform it into an exclusive settlement, mimicking the success that suburban communities were having.

Noted for its Six Corners intersection at Milwaukee, Irving Park and Cicero, the neighborhood (and park sharing its namesake) was taken from a portage that linked the Des Plaines and Chicago river to modern day Irving Park Road.