Watching "City that Never Sleeps." I swear this scene was used in an M Squad episode. Haven't located it in M Squad, but will look. Additionally, I don't think this is on location in Chicago. Note the incline in the background. Lastly, there is a blinking sign in the shot (it was off when I grabbed the screen), "Stack Building" and I find no Stack Building in Chicago phone books.
[url=http://www.flickr.com/photos/52922702@N03/5685023291/]Picture11[/url] by [url=http://www.flickr.com/people/52922702@N03/]Rustymuscle[/url], on Flickr