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Slow down, everyone. I appreciate the suggestions, especially Poysyn’s, but my OP isn’t really about breaking into modelling. I’m sure that in the unlikely event things ever ended up going that route, then advice about how to become a runway model would be invaluable and Poysyn would clearly be one of the first to turn to for insight. 
GlamourShots is essentially what I’d be looking for, as far as franchises go. Trouble is, the nearest franchise to me is 30 miles away. There’s gotta be something closer in Chicago. While it’s probably true that the going rate at a franchise is more affordable than hiring an independent professional, going to a freelancer or a class with a “barter offer” (they get a model, I get free photos) sounds like it’d be cheap but with mixed results. Sounds like a good way to get one’s feet wet, though. What kind of art associations are there that I can contact for this stuff in Chicago? I’d imagine there are tons of photographers who belong to such an entity, but my online searching is coming up short. I’ve only come up with associations for art dealers and photojournalists. The CPPA (Chicago Professional Photographers Association) doesn’t seem entirely helpful, at least from skimming the website … seems more oriented towards photographers who’re actually practicing the trade.
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Even more advice 
I am sort of going this route right now, I am supposed to be competing in a contest come late summer and need to get a few shots done before that.
The photographer should just be one that you like their work. Most professionals are familiar with using models - but not all are good. Check them out online and look at their work. Make an appointment to talk to them. They should make you comfortable and be easy to chat with about what you are looking for.
As far as make-up and hair goes - it depends. If you have the cash you can shell out for a pro, or you can call some beauty schools and see if anyone wants to help out in exchange for some portfolio shots of their own.
If you are lucky, you can end up bartering the whole thing (what I did). You can find a photog that has an interest in expanding their portfolio, stylist and make-up person for the same and you get to be the model.
If not it can end up costing some serious bucks - barter what you can. As the photog (within reason) if there are some shots he has wanted for a while. Be upfront with what you are comfortable with.
If you end up having to do your own makeup, take out some books, Bobbi Brown, Laura Mercier and especially Kevyn Aucoin have some excellent books out there and can help you practice some “looks”.
If I can help anymore let me know.