I have finally finished watching like 117 episodes of M Squad with Detective Lt. Frank Ballinger (Lee Marvin) driving his Ford around the late 1950s streets of Chicago. Most of it is second unit insert stuff, but you can tell Marvin is driving a lot of it. There are even a few examples of in-car process shots where Ballinger is driving and yet his own car can be seen through the rear window in the background. Sort of like Ballinger tailing Ballinger (which would be a whole other sci-fi plot, of course). There are winter shots filled with snow and slush, which I as a Rust Belter appreciate immensely. And Chi-Town looks like I remember it. If you're a native of Chicago, you might want to check out the TV series. Even if you're not as old as I am.
I especially like these two shots of the old Randolph Street Greyhound station. Spent a little time there. Back in the day.
(Also see Chuckman's Collection of Chicago postcards and What Makes The Pie Shops Tick flickr photostream.)
I watched all of these recently, also. I got the same feeling you did about NYC while watching The Naked City episodes (and movie) as it was filmed on the lower east side where I grew up.
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