I am on the far south side of Chicago, but I will be happy to ask my trainer for suggestions for your son to resources and trainers in his area, if you like? My obedience trainer is a member of APDTA, which would be a good place for you/your son to start, here is their website: http://www.apdt.com/
Every APDTA trainer uses humane, non-confrontational training methods, so you can be sure you won't end up at one of those training centers that preaches "dominance" and other nonsense. (I once had a trainer tell me, when one of my Shelties was reluctant to sit on command, that I "shouldn't let that dog get away with that"! Gah! That same center liked to take big dogs -- Dobes, Rotts, and "establish who's boss" by yanking them around. I hope they're not still in business ... but that's a whole other rant.)
I will ask a couple of people for downtown resources, including dog day-care centers, and post back for you if you would like. (Many dogs love day-care, and it needn't be an everyday thing, even going 2 days a week makes a nice stimulus for a puppy. Something to think about!)
Chicago is very dog-friendly, for the most part.