You should connect with @Brie Schmidt as she knows and understands the Chicago zoning laws, but my gut instinct would be that you would be better served looking into a duplex down scenario.

This is a great place to learn and to connect with people so take advantage of all the great resources.

Plus availability .China-  would buy ahead your electric breaker boxes and out let connections.

They cost slightly more than the normal permitting process, but I usually have permits in hand in a week or less.My GC is has some experience on Coronado, if you would like I can connect you, so you can get his opinion as well.

I would love to connect and discuss further how we would be able to assist.

Let's connect and discuss!

Yes well defined rule are very important and help but these are humans were talking about so you have to go deeper then that and consider that human aspect for community/shared spaces. 

Hello Gabriel,I'm currently live in Milwaukee but grew up in Racine, lets connect!

I'd suggest connecting with a Real Estate Attorney, and going from there. 

I know a lender that can help with both states that does investment lending for very cheap, it would be worth a connection as you look to build out your team no matter what you decide.