Slot Machines for Bars in Montclare, Chicago

History

William Sayre claimed 90 acres of rolling land here, and he and his neighbors grew hay, oats and corn and took Grand Avenue to sell their produce at the Randolph Street Market downtown. In 1872 Sayre allowed the Chicago & Pacific Railroad a right-of-way across his farm, and Sayre Station was built on it. Developers platted another farm in the area a year later and named the town and the depot Montclare, after Montclair, New Jersey. The rail line failed in 1873 and passed to the Chicago, Milwaukee & St. Paul, which ran a single commuter train a day, so lots stayed vacant and some 120 residents kept farming.

Chicago annexed Montclare in 1889, but growth waited until 1912, when the Grand Avenue streetcar line extended service here. Utilities and paved streets came in the 1920s, and single-family bungalows became the standard house. In 1916 the Northwest Park District began building a fieldhouse on land the Sayre and Rutherford families had donated, in what became Rutherford Sayre Park. By 1970 Poles, Italians and Germans were the majority, and by the 1990 census Greeks, Ukrainians, Lithuanians, Lebanese and a growing number of Hispanic residents had joined them.

The area today

Montclare hugs the city's western edge, nine miles northwest of the Loop, and in 2020 WTTW News called it a classic bungalow belt of single-family homes and apartment buildings. Rutherford Sayre Park, on Belden Avenue, is its main public ground, with a fieldhouse that holds a gymnasium and fitness center, plus baseball and softball fields, a football-soccer field, a roller hockey rink, tennis courts, a community garden and a natural area. The Mont Clare Metra station, on Medill Street, serves the Milwaukee District West line, and CTA bus routes 65, 74 and 90 connect there. Housing north of Diversey Avenue, built from the 1930s, mixes bungalows, ranches and Tudor houses.

Bars and restaurants here

Harlem Avenue and Grand Avenue carry the neighborhood's trade. Grand was the farmers' road to the downtown markets, and the retail strip at its corner with Harlem was the only shopping here before the war. In 2020 WTTW News called Harlem the backbone of the commercial corridor, lined with ethnic food shops, furniture stores and hair salons, and it noted many senior citizens among the residents. Kolatek's Bakery on Harlem was on the Sun-Times list of paczki spots in February 2026.