to be honest, most the shows are in Elks Lodges and of the like. no high schools, lol.
it's funny, in a legitimate way. not stupid and cheesy like WWE. the wrestling is also top-notch, a show will usually have lots of high-flying, lots of wacky lucha-inspired submissions, more traditional wrestling, some straight up striking... it depends on who is on the show.
i can't really compare it to any other promotion. WWE and TNA are all rigorously scripted and rarely turn out funny. ROH is known for being serious business. Chikara combines colourful characters, damn good wrestling, comedy that doesn't insult one's intelligence... a good time, family-friendly, fun stuff.
the promotion has really grown over the years. seeing some of the older stuff will help one understand their beginnings... but they've really been stepping up their game as of late, filling in that spot where CZW and IWA-MS have been lacking (that spot being the indy level under ROH).
their best of dvd's is a great way to start. also they have a weekly podcast (also available on youtube). individual matches stand alone well, whole shows may have a slow moment or two but are overall very watchable.
http://www.chikarapro.com/indexENG.shtml