@Drew Flowers welcome to the forums! You are in the right starting place here to learn about the city and the surrounding areas. I would check out the Straight Up Chicago Investing Podcast that @Mark Ainley and @Tom Shallcross host. You should also find some local meetups. There are a lot of great meetups locally that you can join (virtually right now). Once you know the lay of the land you can make decisions on your investing strategy. 

@Drew Flowers

Househack! I wish I did this when I was in college. If I could go back, I would buy a SFH and find roommates to help pay off the mortgage.

Welcome! Educate yourself with the forums, real estate rookie podcast, books in the BP bookstore, introduce yourself to other investors. Learn and narrow down what type of real estate you would like to go into. Try to make investment goals for yourself like how much cashflow, COC ROI, etc you want to target. Also become an expert on the numbers... use the BP calculator to start understanding how to determine if a property produces good returns or not.

As recommended, house hack is great reduce / eliminate your personal housing expenses.

Get solid, consistent W2 income and the house hack. Having some real income and tenants paying down your living expense will make every other strategy you learn about WAY less of an uphill battle. 

I agree with everyone above - house hack! I am 20 and am about to start mine once I get out of school. I would be doing it now, but I go to school in NYC which makes it nearly impossible. Educate yourself as much as you can - listen to podcasts, ask questions on the forums, read books. After that, take action! Don't sit on the sidelines, experience is the best teacher.