My in-laws live in the Chicago area (5 mintues from ORD) and eventually
we'll be doing a weekend trip up there, but I want to do a few shorter trips
first (~1 hour v.s. the 2.5 to Chicago). Both to build up experience in
x-country flying and to get my wife more used to the idea of flying for
longer stretches and for travel.

When you do this Chicago trip you might not exactly want to land at
O'Hare. Paulwakee or Dupage are doable and maybe even Midway if your
feeling a little crazy, but I wouldn't go nowhere near ORD. Anyway, if
you do go into ORD let us know how it went.

Rick