Chicago’s Tri-Taylor neighborhood has always been one of the city’s more ethnically diverse areas. It has a long history of Italian influence, due to its proximity to Little Italy. Tri-Taylor was once closely connected with Chicago’s Italian community. However, construction of the Medical District geographically separated the two and significantly scaled back the number of homes located in Tri-Taylor. Next came the Eisenhower Expressway (along the northern border of the community), which also cut into the neighborhood’s residential streets. And in the 1990s, the Chicago Technology Research Park was built on roughly 56 acres of Tri-Taylor’s remaining land, again cutting the size of inhabitable space. 

The changing landscape in Tri-Taylor led to shifting demographics over the years. The more recent community identity is shaped by a predominantly Latino population. Still, its Italian ties are visible in the several Italian delis and pizzerias found on West Taylor Street. Sub shops seem to be a dime a dozen around these parts, but you can just as easily find somewhere to get a good burrito or the fixings to cook an authentic Mexican dish at home. There are Mexican restaurants, bakeries and super mercados (super markets) on both Taylor Street and Western Avenue (another main commercial drag of the neighborhood). 

While much of Tri-Taylor’s northern half is occupied by large industrial parks and out buildings for the Medical District hospitals, the southern portion is quite quaint, with red brick row houses, tall trees and grass-covered yards. The distinctive row house architecture dates back to the 1870s and features Italianate facades, indicative of the area’s 19th century residents. Many of these beautiful vintage dwellings are located on Oakley Boulevard. Other residential blocks have mainly two and three-story flats with a number of newer condo constructions and apartments here and there.

Tri-Taylor is a very small Chicago neighborhood, which makes it easy to get around on foot or bike. It is only about five blocks wide and seven blocks long, located approximately three miles west of the Loop (downtown Chicago). The Blue Line public transit train runs along the northern border of the community and has two stops in Tri-Taylor – one at Western Avenue and one in the Medical District. If you have a vehicle, the Eisenhower Expressway (I-290) is easily accessible from Congress Parkway at Oakley Boulevard and Damen Avenue. Once on the highway you can navigate south by way of the Dan Ryan Expressway (I-90/94) or Lake Shore Drive.