Hi @Christian Bateman
Investing out of state (or like me - out of country) can certainly be done but you need to get very familiar with the market. Chicago is a notoriously block-by-block city - everything you think you are buying based on the "area" can be undermined by choosing a bad block. You may be able to get a general idea of an area from on-line resources but nothing replaces good old "boots on the ground". It's essential that you build a team in your chosen market. I would recommend getting multiple opinions on a specific location (broker, property managers, inspectors, police, local businesses, etc., etc.). Also, make sure you have some back-up team members if any flake out.
I'd recommend going to the market and really learning it - time spent with your team in the market is invaluable.
By the way, you will want to start narrowing down your focus to a few neighborhoods - there are over 70 neighborhoods in Chicago alone and many more markets if you consider the different areas and blocks found within each neighborhood (not to mention the burbs).
Good luck!