Appears to be Chicago. Milwaukee doesn't have elevated trains, but Chicago had the Milwaukee Road Railroad.
I believe you are correct Sir. When I saved the picture it's name was "Chi" which leads me to believe it is Chicago.
What a lot of beautiful automobiles! It's hard to pick a favorite. I like the pastel Chrysler hardtop wagon on the left. That 58 chivy 4 door is pretty slick too!
I actually like the Newport, appears to be a '65(?), because a former friend had a '66 that I put a replacement TF into, and I fit sooooo nicely behind that yooge wheel!