A lot of what you want to see will depend on your ability to get to mobile transportation, aka a car. There's a lot to see relative to other cities but what there is is dispersed widely between Chicago, southwest to Joliet, and then southeast to Gary. Unlike Detroit, where I could trip and stumble and find my way into somewhere easy no matter what.
As far as a "scene" goes, well, I'd say it isn't as large or deep as, say, the Twin Cities or Detroit, where there's a large subcultural history of exploring (underground stuff mostly in the former, abandoned stuff in the latter), and are the other two Midwestern cities whose scenes I know.
There's a newer generation of younger twenty-somethings around now. At 30, when I got started exploring with others at 18 or so, I was a baby and every other explorer here was around 8 or more years older than me. Now I'm old.
They seem more inclined to larger social gatherings than say, the old CUE gang I hung with were. I'd look around on here for some of them.