I've posted this particular counter stamp before but had no idea what it's back story was. Here I found it attached to these Chicago Sesquicentennial information cards. There are a bunch of cool historical facts on these folded cards. Being in the Chicago area I took immediate note to the 1779 entry about Jean Baptiste Point du Sable being the first settler. Just recently the city counsel wanted to rename Lake Shore Drive after him. They compromised and it is now called... Wait for it... "Jean Baptiste Point du Sable-Lake Shore Drive". politics.
Sadly those "three of the five tallest buildings" are no longer in the top twenty. I remember when the Sears, er, Willis Tower was the tallest in the world (now #23). Not even the tallest in America now (now #3).
For some reason I really liked this particular counter stamp. It is of a fox jumping over a star on an 1881? IHC. (Kind of guessing on the last two digits of the date. They were pretty damaged at some point. Not sure if I'm seeing 81 or it's Pareidolia.)