I had heard about the Millennium Park in Chicago. It seems Apple's 3D mapping textures on to altitude data leaves a little to be desired. There's a mirrored-glass skyscraper about three or four blocks west of Navy Pier that looks like it was visited by the Martian's Heat Ray. (I was going to say the Melty Man, but one must never mention his name out loud
)
That kind of looks like the Pritzker Pavillion. AND I just loaded it up on my phone, and it looks totally fine. Seems like people are being a bit too picky. Looking at the loop and Michigan Avenue, I'd say they got it pretty good. Sure, the glass on the Trump tower looks a little funky, but the buildings sure are identifiable, and accurate.
Personally, I can't stand the 3-D modeling in any of the maps. And find it is distracting when trying to use, particularly when its more than a generic building shape. But that's just me...