Well I guess I just get ignored - you should know I live in Chicago good sir.

I am very familiar with Red Frog Events...super cool company, we used to be in the same office building as them until they moved out. I hear they have a slide in their offices. Good luck with that!
1.) I can't give you specific complexes as suggestions - really everything fluctuates, some people own condos and rent them out...others are complexes owned by companies. I'd recommend you use The Apartment People (
http://www.apartmentpeople.com/ ).... they are who I used to find my place. However, since it's just for a few months, craigslist might be your best move.
2.) These are the only neighborhoods you should consider:
North:
-Wrigleyville
-Lakeview -> This is where I am located.
-Lincoln Park
A little more south/west, and full of hipsters:
-Bucktown
-Wicker Park
Near North Side (note: these will all be substantially more expensive, personally I don't think it's worth it):
-River North
-Old Town
-Streeterville
3.) I don't need a roommate (cat + gf is more than enough) but could ask some friends if anyone has anything for those few months.