Joe, I can't say I would start with wholesaling, but to each their own! I started much where you are and before I dove HEAD FIRST into real estate investing, I tested it out with a small, SUPER affordable condo in an up and coming area. I targeted the very West edge of Logan square about 5 years ago (knowing all things move West in Chicago :). It's been a great strategy for me. I've been able to add those small, affordable, little condos each year for the past 4 and purchased my first 3 flat this past November.
While some people like to BIG BANG their entry into RE investing, my advice for someone just starting out would be (1) don't get in over your head financially (don't do a multi unit right out the gate) (2) pick something small to TEST it, hell you may not LIKE doing this whole real estate thing after all (3) Don't buy a major reno, on the whole, houses are old in Chicago, so MAYBE take on a small cosmetic fixer but don't pick something that needs a ton of work. It ALWAYS costs more and takes more time than you think especially when you start and don't know what you are doing (4) starting small lets you learn how to manage everything about it from picking tenants to scheduling repairs, etc. The education is invaluable (5) After a year of doing all that, decide what your next property should be :)