Jeep people are probably some of the coolest people to go to events with, partially because they all LOVE their vehicles, but when you're off roading it's like a cruise, but while the drivers are making their way through, others are helping, chatting, watching, giving advice, etc. I will be going to the Cliffs down in Marsailles, IL this Sunday for a fellow Jeep owner and friends birthday. Badlands is another good park, but about double the drive. There's some local clubs, I know Down and Durty Offroad had a few members that used to frequent Luke's the past two years. It's definatley a different pace, but the more and more I get into it, the more I'm hooked. I have the same truck as Ryan's, but a smaller lift and 31" tires (the size of the ones in his first pics, but as aggressive as the ones on the rack) I DD'd it to the city 6 days a week and drive it all the time out here. It doesn't see much off road, but it's by no means a mall crawler.
Edit: I also live in Lake Zurich, so it's a bit more common to see an old lifted beat up jeep here than say in Downtown Chicago lmao.