I saw Chicago twice, 26? years apart. They are the very first and last concerts I've been too, mainly because I didn't have a car in 1984 or when they came to the Western Idaho Fair a few years ago.
I spent eight or nine trying hours at the H.O.R.D.E '98 Festival (Blues Traveler...) and while it was ultimately a lot of fun, it's not a thing to do if you are broke and have to wander about to beat the heat, the venue was in no fu--ing way serious about what the heat could do then and it was a big carnival of merch.
Of course, once the sun started going down, the real fun stuff happened on stage.
I never saw Family Values or Vans Tours although they came here.