There are lots of great places in Illinois he could go! Sadly, Normal is much too small, and we only have one chain bookstore left now that Borders has closed. Naperville isn't accessible by train, so I had to skip it, but there are some really good bookstores in Chicago proper. Not to mention Champaign-Urbana.
Quick segue: I think it would be amusing for Harry to do a job in the actual 'state' of Illinois. Chicago is pretty much a city/state in its own right, and has little or nothing to do with the rest of Illinois. If only because there are so many hilarious place names. Cairo = Kay-row, Vienna = Vie-anna, San Jose = just like it's spelled, literally, Versailles = Ver-sails.