The Chicago fam is probably more than 90% legit, except for some gambling schemes and possibly prostitution and few robberies here and there.
Those are not cheap street whores either. Very pricey call girls that work exclusively for them and only them and frequent River North Hotels to conduct their business. Chicago has so many trade shows at McCormick place on a weekly basis that there is so much opportunity for profit if you are an escort and in charge of them. Lots of horny businessmen who are visiting from out of town that want their dick sucked.