Let's dive right in. There were a couple of really great guesses from Zymurgy and dobalovr.
This is Detroit Michigan. The orientation of the illustration is looking SOUTH toward Canada and the Detroit River.
When I first saw it, I knew several of the buildings, but they were "out of place" relative to each other. But NO DOUBT many were downtown Detroit structures.
Note there is NO other position along an imaginary 180 degree arc (the flat side of the arc being the Detroit River) that would put these buildings in the proper location versus each other.
So, lets look at some of the buildings identified.
Right in the middle of the illustration, is the Hudson's Department Store, once the biggest department store in the world. Distinctive shape, with the flagpole on top and the "Hudson's" name. It was imploded in 1998. You can use its position in the photo to see how in REAL life, the illustrator has moved things around.
I tend to like these implosions .. but this was actually a sad day for longtime Detroiters.
Then below, the Broderick Tower and the David Whitney building, in real life just across the street from each other, and just NORTH of the Hudson Department Store on Woodward. The illustrator has clearly taken "liberties" with their placement.
Photo below is looking SOUTH on Woodward. First photo above of the Hudson's building is looking NORTH on Woodward, and you can see The Broderick Tower and Whitney Buildings just up the street.
The tallest building in the illustration is Book Tower below. It is to the WEST of Woodward and one of the most recognizable buildings in Detroit to this day.
The Stott Building, in the illustration AND in real life, its ABOUT in the proper place vis-a-vis the Hudson's Building BUT too far to the WEST. You can also see it in the first photo of the Book Tower above.
I can identify 14 more downtown Detroit buildings, and even one from 2 miles away in "Mid-Town" (near the OLD GM HQ building) .. but you get the point i hope
The clues:
1. Self evident now. Detroit is East of Mississippi, North of the Ohio, and West of Pittsburg. BUT, so are a LOT of cities. So, Clue 2 and Clue 3 to cut down the search.
2. The big GREEN SPACE between the car and the skyline didnt exist in Detroit -- its a completely urban area since the late 19th century. PLUS there is NO elevation -- its virtually flat as pancake within 20 miles of downtown -- that would allow that vantage point versus downtown. 100% artistic license by the illustrator.
Today, Comerica Park, Ford Field, and I-75 (Fisher Freeway) are there. 60 years ago there were a great many buildings - and Fisher Freeway - standing there.
3. This clue was designed to separate Detroit from Cleveland, Dayton, Cincinnati, Toledo, Milwaukee, Chicago, Indianapolis, et.al -- the likely cities with BIG downtowns and several TALL buildings.
a. I singled out the Hudson's building. Told it was imploded (note had you googled "downtown implosions in michigan", the first hit might have been video above and you were in Detroit
).
Joseph L Hudson, the department store magnate, was an investor in Hudson Motor Car, formed in Detroit in 1909. He let the other investors use his good name. If you identified THAT building, it put you in Detroit and NO OTHER city.
b. I indicated you should look for 1960-1990 era photos IF you had a hunch .. just the TALL buildings in the illustration and look for the shapes. NO other city in the search zone has ALL these buildings.
DETROIT - 1960. Looking NORTH on Woodward.
Hudsons, Book Tower, Whitney, Stott .. all there. The tallest NOT in the picture (in fact, this photo likely was taken from it) is the Penobscot Building which was actually the tallest in Detroit (fourth tallest in USA for a bit) until the Renaissance Center in 1976.
Note it was NOT in the illustration .. in real life the Penobscot WOULD have been clearly visible as the tallest structure by far. More artistic license by illustrator to leave out the one of most recognizable buildings in the world at the time.
c. The insect image was from the AMC Hornet emblem. AMC was formed from the Hudson Motor Car and Nash Kelvinator merger in 1954. The "Hornet" name came from Hudson, namely the Hudson Hornet.
This was a challenging puzzle. As with MOST of these games, the structures are the key usually. Identify them, and you're done. The clues, well I try cut down the search area from anywhere in the world, to a managable area -- but also not "give it away" either such that its no challenge at all.
Anyway, once again, hope one of you 'hosts" one one day. I will again if I find a suitable photo
