Hey (Bennett?) good to meet you!
There are a lot of small clubs in town but it's mostly people that have known each other for a while. It sometimes looks super-cliquish to new riders, but it's not, people are mostly pretty friendly, you just have to understand that some of us have been riding together for 15 years or more, and we've seen clubs and people come and go, so we tend to stick together with our old friends out of habit, even though we like making new ones.
A guy named Eric started that Chicago Scooter Club that (our) Eric posted, I haven't seen him for a while so I don't know how active that club is. There are some Yahoogroups:
http://groups.yahoo.com/group/CHIscootEvents/
http://groups.yahoo.com/group/CHIscooterList/
but they've been pretty slow lately too. With spring coming, watch "Events" for rides and parties and such, and usually there'll be at least a few of us going to all the other rallies in the midwest over the summer, usually making plans on the "List"
The big local rally is Slaughterhouse, over Labor Day weekend, and this year Amerivespa is in Lake Geneva in June, so you won't wanna miss that, it's probably going to be the biggest rally in the midwest ever. (it's open to all scooters, not just Vespas).
There are some suburban clubs, mostly maxiscooter guys, and always new clubs popping up downtown, but like I said, better just to meet everyone first and show up for some rides and see what happens than getting too concerned about clubs. And it never hurts to help out at existing events, and organize your own. My advice there, is to make an effort to get involved, but on the other hand, don't try *too* hard… buy a round of drinks, offer to help, maybe plan rides and events that interest you and don't conflict with existing events, publicize them the best you can, and just enjoy yourself. Even if the turnout is small, you'll meet people over time that share your interests.
Hope that helps!
Bryan