Of course it's possible! Especially if you opened up your own salon (there are always women out there who want pampering, so if you're there, customers will come)
And there is always an industry for doing wedding, party and prom make-up.
I don't know if there is any sort of Chicago fashion week (usually most major cities have a fashion week) but you could get hired to do make-up for runway shows. Plus, there are always photoshoots going on.
The toughest part will be getting into the circle and knowing the right people, but once you advertise yourself and get your work out there, people will come to you. When you start up get advertised (maybe in a local newspaper) and start a website with a gallery of your work.
Best of luck! Don't give up on your dreams because your dreams never give up on you :)