If Naperville feels isolated to you, try Evanston, about 20 minutes north of the city on the lakeshore. That's probably the best mix of diversity/good schools/city living you'll find. Like Oak Park, some areas are better than others. Expect to pay more than the O'Hare suburbs, but if square footage is not your biggest priority, that may be the best place to have a more urban/sub-urban experience.