This advice may be rubbish, as I'm not too familiar with the cost of living and wages in the Chicago area.
I do think that if this is a priority to you and your boyfriend, it's possible. You'll have to take a serious look at your finances and be realistic about what you can and can't afford.
Start by making a list of your bills and find out what you'll need to make collectively to stay up to date with payments and then add in cost of living, groceries, gas or public transportation passes. Maybe his school will offer a discount on public transportation.
Good luck! Sounds exciting