It looks like that might be Immaculata High School in the upper left corner.
Original caption reads: "View of a road in front of the construction site of a new drive at Irving Park Boulevard and Sheridan Road in Chicago, Illinois. A roadblock, a building, and a horse-drawn wagon are visible in the background."
Cite as: DN-0085752, Chicago Daily News negatives collection, Chicago Historical Society, Library of Congress.
Summary from Wikipedia: Immaculata High School was an all-girls' Catholic high school located in the Uptown neighborhood of Chicago, Illinois. It was open from 1921 to 1981. The campus buildings received Chicago Landmark status on July 27, 1983. Still standing at Irving Park Road and Marine Drive, they were designed by Prairie School architect Barry Byrne, a onetime apprentice of Frank Lloyd Wright.
Image courtesy John C.
My grandmother Elsie graduated from Lake View High School in the 1930s; I forget which year off hand. She married my grandfather Edwin shortly after.
This is one of the earliest postcard images I've seen for the area. The Pattington was built in 1906 and is currently listed on the National Register of Historic Places.
In 1995, the Landmarks Preservation Council of Illinois awarded The Pattington the Richard H. Driehaus Preservation Award.
Top image courtesy John Chuckman; bottom image courtesy Google.
