The northwest side of Chicago is an appreciation play, not a cash flow play, so the first thing you want to ask yourself is which makes sense for you financially. Given that you want to live in the house, I assume that you look more for appreciation and long term holding than cash flow on immediate rental.
Keep in mind that the new mayor has made noises about rent control (e.g., allowing people to "age in place" and considering stopping water shut offs as "inhumane" (not that she could do it, because there are bonds issued against water receipts, but the mere fact that she is considering it speaks volumes as to her financial literacy, her willingness to cater to the interest du jour, etc.)), and "multi-unit" covers a multitude of sins - duplex, three-flat, six-flat, etc.. So you may want to consider that appreciation won't necessarily be what it was. I had high hopes for Mayor Lightfoot, but I fear the poverty pimps have taken over City Hall.
Look for niche neighborhoods and niche renters, and remember; transportation costs and housing costs are one and the same. For example, if you live near the Blue Line or the Orange Line, apartments or even bedrooms can be rented out to airline pilots and stewardesses. Why? Those lines connect to the airports and you can market accordingly.
Don't forget the South side. Southwest Chicago housing stock and businesses is almost a doppleganger of northwest side areas, but cheaper due to higher minority (usually latino) presence and general North side snobbery. Find areas with convenient mass transit to downtown or Midway (if airport is your market) and you can get some cash flow (not great, but some) and some appreciation.
Just ideas, feel free to ignore, but until you tell people what your druthers/tolerances are, not much advice people can give.
Oh -- NETWORK, NETWORK, NETWORK