In illinois, prosritution is a class 4 misdemeanor, ad is solicitation of a prostitute. Professional domination and submission us also prostitution in the eyes of the law.  If you want further details, I suggest you google. Chicago municipal codes are stricter than state laws; the penalties are higher.  Busts usually aren't conducted by city police though.  

There are of course ways to circumvent police.  Ladies that are reviewed, have websites, and are part of verification services like RS2k, p411 and  date-check are a good place to start. Ladies requiring some form of verification are a lot more legit than a random stranger telling any dude off the internet to come to her incall.  

A cop can go through an entire session and bust you at the end. Yes it's entrapment. Yes it's not legal. That does not matter. It is the cops word against yours.

Doing your research will help you avoid these matters, however.  Be smart. Chicago is hot with LE activity right now.  

I wish you luck on finding a dominant lady who isn't either tattooed it fuller figured, though.  All of them that I know, including myself, are either fuller-figured or tattooed/alternative looking. I'd be interested in knowing about dominant lady providers that aren't either full-figured or tattooed.