Originally Posted by
cordelli
the ability to have the commuting expenses picked up so you can make sure it all works out for you.
Though, of course, if you move you won't get those 1,400 or however many miles it is a week.

1. If I am reading the OP's post right, I take it to mean that the Chicago company is getting his a long-term stay place or even just an apt. lease there. So in that case, flying to ORD on Sunday evening, late enough to have Sunday dinner together, might work best (again, more time away from the family, but OTOH it avoids any potential hassles with Monday snafu's getting to ORD).
2. My calculations show nearly 75,000 FF miles and ~100 EQS over the next year, assuming NO other travel besides the weekly EWR-ORD r/t. That would a) be mid-tier elite at least, and b) provide for family vacation each year (assuming availability at 25k a pop, x3).