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Do cities even really have welcome signs? I think the only Welcome sign for Chicago is when entering the Chicago Skyway from the east, and it isn't anything special. Just says "Welcome to Chicago" and then the current mayor underneath, in typical freeway signage and font.
State welcome signs are a different story though.
Chicago has one at O;Hare too that I have not seen in years. I believe it has a view of the city and says Welcome to Chicago.
birmingham had this one back in the '60s, before the train station in the background was torn down (i know...):
a new sign intended to sort of pay homage to it was installed at the entrance to a 4-block long park in the middle of the city a few years ago:
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