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I'd just like to develop a thought process to get started in here so I can spend the next 4-6 months doing some research before I make a move. FWIW, I think I could EASILY get 2500/mo and probably closer to 3000 or 3500 for this place, but i just don't know (does anyone know how I can figure out what I could get)?
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I think you're aiming too high in your rental estimates. The Chicago market has really experienced tremendous growth in housing supply, which has translated into a soft rental market. Take a look at craigslist to get an idea of what 3 bedrooms are renting for. It will also give you a sense for how many individuals are looking to rent out their newly purchased condos. My sense is that there are a ton of people who bought places without ever intending to live in them, instead hoping for a quick flip.
Search results from Craigslist, 3 bedrooms in wicker park
Unless you truly want to be landlord, I don't think it's a good decision to rent out this place. Between the vacancy periods, management fees, and generally soft market (with inventory building and building), I wouldn't want to be a landlord in the Chicago market unless I had a truly unique property with a well-defined pool of renters.