If one can travel as far as Iberico from Sears Tower, that sort of implies all of Randolph Street is fair game, and once one has a car there is Taylor Street and who knows what.
Trattoria #10, 10 North Dearborn used to get lots of good write-ups before the dawn of time (or at least before LTH Forum) and should be sufficiently non-threatening Italian.
Wishbone, 1001 W Washington does southern-style comfort food in a diner-like setting quite well.
And Ina's, 1235 W Randolph is another American comfort-food style place that I have heard good things about and never quite tried myself.
So seriously, tell us what kind of food you would like, and there probably is something darned good within a couple of miles.
BTW, I agree that Chicago Greek, as non-challenging as it may seem to us, would be terribly alien to my farm in-laws, for instance.
d
Feeling (south) loopy