T.D.
Get a recruiter (it doesn't cost you anything)! I'm a restaurant management recruiter - most of the people I work with are relocating. Look online, find a recruiter that has a lot of searches/needs in Chicago...let her do all the work for you. They already have leads, contacts, and probably know a lot about the area. Unfortunately, a lot of hiring managers just skim over the cover letter. A recruiter can call the hiring manager and say...."I have the perfect candidate for you (and this is why)! She's coming to Chicago in July!!" The recruiters know who's looking and they have a good raport with the very companies you want to get in with....they can negotiate everything for you (pay, start date, benefits, etc). Seriously! find yourself a recruiter.