Do you mean shit as in rough, shit as in boring, shit as in overpriced? The times I visited I was mainly just bowled over by the incredible architecture. Went to some cool bars and restaurants and stuff, dunno if they were life-definingly wonderful or anything, although the view from the restaurant at the top of the Hancock Tower
was pretty special.
@padraig (u.s.) to thread, please!
I've worked downtown for 7 years. It's hot trash, with a couple exceptions, unless you're a yuppie or (no offense) a tourist.
The loop proper is, unsurprisingly, almost all corporate, with a fair bit of luxury residential as well. The areas (I wouldn't call them neighborhoods) around the loop - River North, Streeterville, Gold Coast, West Loop, South Loop - are even worse, an endless cavalcade of finance bros + Karens and/or tourists, depending where exactly you are. Some of them are even beyond yuppies at this point, like condos regularly go in the West Loop for $1m+.
There are indeed cool museums (Art Institute, Museum of Contemporary Art, Field Museum), interesting architecture (tho being rapidly torn down + replaced w/boring skyscrapers) and some nice views, but that's about it. If someone was actually visiting I could clue them into a few decent spots in greater downtown but really the only reason to go downtown at all, if you don't have to, is to go to the AI and/or MCA.