Oak Brook Illinois is an archetypical midwestern suburb --- strip malls, chain restaurants, vast residential areas, centered (like San Mateo) on a big shopping mall --- that happens to host a bunch of high rise office buildings. No doubt there are lots of people who work in those buildings and choose to live in Oak Brook so they can walk or take the Pace bus to work. But that doesn't make the living experience of Oak Brook comparable to that of Chicago, or even Milwaukee.
I'm not trying to say that San Mateo is irredeemable. If I had to move back to the Bay Area (crosses self), I'd probably look at San Mateo before San Francisco, because I have kids, and San Francisco seems like an awful place to raise kids. I'm just saying that it is not a realistic substitute for San Francisco for city dwellers.