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There are probably going to be poetry, art, writing, live role-play and possibly some sort of food eating/food making contests.

Poetry: Hah-hah-hah. No. I don't know the first thing about poetry. Or rather, I do and I can't make it work.

Art: Heh-heh-heh-heh. No. Same reason.

Writing: I would be interested in this. I'm a speed reader and have a good eye for SPAG so I'd probably do well.

Live Roleplay: *backs away slowly* Personally, this scares the heck out of me for some reason. That said, I could probably judge it.

 For hooking up the DJ station: More is needed than just speakers. For the speakers to work, you need to have an amp. To be able to control stuff adequately, at least for someone who knows sound a bit, you need a pre-amp and sound mixer. I'm not precisely sure how easy it would be to do without the pre-amp and sound mixer as I haven't worked without either.

Hmmm, a judge, eh? *grins* Put me down for anything involving food, doncha know. I'd need to break out a Salamandastron Hare costume then...

Me: grpmphsnch. This is good stuff.
Assistant: So does this one win.
Me: Dunno yet. Get me one more of those and another of these. And something to drink.
Assistant: *stares for a moment*
Me: Chop chop.

What are the other sorts of contests? I just know that food oriented ones just leap out at me from memory, but, if you had the room, you could have lawn darts and other such things that were played on Namedays. Although I don't think we'd have room for croquet...

 *pokes* I'm here and willing. I don't know what I'd be particularly good at.

I can tell you anything related to visual arts would be a no-no.

A note that I don't think you've adressed is the access to sound equipment. Generally, what I've seen is that when you rent out a convention center, you've got to rent the sound equipment separately. Most times, the person who rents it out sets it up and everything along those lines, but you'd still need to find a contact for it. And, from what I can tell, you'd be better off having two independent sound systems. This is, of course, if my assumptions are correct. Anything wrong with the following would of course change the rest.

1. The DJ would be playing music all through the event, regardless of if there was a speaker or not. Therefore, he would need a few channels separate from the stage both for input (him putting on CDs, announcing requests, etc) and for output (to the speakers that he controls). From what I can tell, he'd only need at most three inputs (CD, cassette tape (?), microphone), unless he's fancier than I'm assuming and has turntables, etc. The outputs would be to amps and from then on to speakers. The amount of stuff in the output depends on how much control and volume is required and/or wanted.

2. Now, for the main stage, I think all you would need are one, or maybe two, microphones for input. For output, it would be the same as the DJ station. Now, if we were to get fancy and have some live music or an onstage drama of sorts, there would be a demand for more microphones and inputs. This is all depending on how fancy you get on the main stage.

How much does renting this equipment run? Dunno, especially not for Chicago. My guess would be somewhere in the 1-3 thousand range, depending on how big you go.

Heh. That was a lot of off the top of the head thought.

This said, I'm not extremely knowledgeable about sound. This is what I've picked up from setting up and running sound at my church and the application of a little logic.

*coughs* Like I said, I'm here and willing.