Chicago historian John R. Schmidt frequently has "Then and Now" features where he shows a part of the city as it appeared when he was a kid against how it appears now. I just found a trove of historical photos produced by the Illinois Dept. of Transportation, including a few dozen from my neighborhood, so I can play the same game.
Here's the intersection of Sheridan, Broadway, and Montrose, looking west down Montrose, from March 1936, more than 80 years ago:
Here's this past Tuesday:
Though some of the details have changed, both buildings flanking the north side of Broadway still exist. But the Wilson Yard development, from 2006, has taken over most of the area between Broadway and the El tracks. And past the El, the mature trees have changed the character of Montrose.
Another thing I notice about photos of Chicago and other U.S. cities before about 1990: the haze. Starting in the 1970s in California and the 1980s elsewhere, governments cracked down on air pollution. Chicago in 1936 would have been intolerably polluted to Millennials. The top photo gives a hint of why.