If he's in Chicago there's a large chess community there, for both unrated and rated chess. For rated events, there is, which lists a lot of tournaments in Chicago and the surrounding area. Of course most of these have entry fees (the notable exception is Roselle which is free, but it's also in Roselle which is kind of far from the city), which might be a problem if he "struggles to get by" as you mention.

There are also lots of casual/unrated meetups without entry fees. I don't know of any centralized website that lists these, but most of them are posted on the facebook group "Chicago Area Chess"..

/r/chess Thread