We used to run an on-premise club there that allowed single males. It's called Couples Choice. Check out their website. The new owners may still allow them on Friday nights like we did. The people we rented the club from back then had been there for decades. It was very nice. DJ, dance floor, bar, huge seating area, plenty of private rooms and a few group rooms, hot tubs. It was hands down the nicest one in Chicago. Best part, it's legal. You don't have to worry about police raids or riff raff getting in. It has off duty cops for security. If they no longer do them, check out Private Affairs in DeKalb, Couples Playhouse , There was another one in Naperville and was one in the city but I cannot remember the names. Good luck, hopefully that points you in the right direction