Chicago has plenty, and I may end up posting more than one*, but here is one of mine:
Source
Formerly the Rock and Roll McDonald's, the company decided to redo one of their flagship locations in densely populated River North, downtown Chicago. In a pedestrian-oriented area otherwise full of highrise development, McDonald's insisted on including a massive surface parking lot & double drive thru as part of the development. Nevermind the location, nevermind the already high pedestrian traffic, nevermind the great mass transit access. Nevermind being surrounded by a gillion hotels and tourists who walk & use the gillions of taxicabs that roam the district. A once in a generation opportunity to redevelop a prime site became...the city-hating eyesore that will last another generation (note: I don't mind the design of the building itself).
And what did the city do to prevent this? Bend over, say "yes, daddy", and take it in the ass. Because after all, McD's is a Chicago area corporation.
* Actually, at the top of this picture is one of my other most hated lots. Note Walgreens' surface parking lot, right in the heart of the city. Thanks for beautifying our city, assholes!