Today, Montclare is the perfect picture of a clean, middle-class suburban neighborhood, but it took more than 100 years, shifting immigrant communities, and a few transportation-related calamities to get to this point.

Although William Sayre threw down his flag to claim 90 acres in this area in 1836 'by right of possession,' he still had to fork over some dough for the land in 1838—a consequence of an inaccurate government survey—when he officially purchased it from the Jefferson Township land sales. Sayre’s marriage to Harriet Lovett the following year was the township’s first official union. With the help of his neighbors Sayre transformed the area into a thriving farming district, mostly turning over bumper crops of corn and oats, which they would then lug down Grand Avenue to sell at the Randolph Street Market in the nearby city of Chicago. The trek to and from the downtown markets was a dangerous one, as farmers worried about trains hitting their wagons or robbers stealing their day’s proceeds on the way back.

By 1872, Sayre gave into progress, allowing the Chicago & Pacific Railroad Company to build over his property. A station bearing his name was built on his farm, but only a year later, the rail line was taken over by the Chicago, Milwaukee & St. Paul Railroad. As a result of this change, only one train a day ran in and out of the area, destroying any new interest for settlers and so, Sayre and his comrades just went right on farming.

In 1889, the city of Chicago voted to annex the township (by that time called Montclare after Montclaire, New Jersey.) Not much changed until 1912, when the Grand Avenue streetcar line began to run all the way into Montclare. The new, easily accessible neighborhood piqued the interest of people hoping to live further away from downtown, but a lack of utilities and paved streets tempered that enthusiasm. By 1920, improvements in the neighborhood’s infrastructure had been taken care of, and families started to move in and build homes.

From the results of the 1970 census, it was apparent that the neighborhood was a popular destination for Italian, Polish, and German immigrants—the contributions of these cultures are still very evident today. Over the next two decades, the population further diversified with an influx of Ukrainian, Greek, Lithuanian, and Lebanese settlers, along with a growing percentage of Latino immigrants. The mingling of so many distinct cultures in one neighborhood has made Montclare a very desirable place to start a family. Tolerance, community involvement and diversity are the strong pillars of this Chicago neighborhood—and the residents like it that way.
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