Option #2 gives you three shots on goal. As a child of two faculty members, I think your chances at UChicago are actually pretty decent. Columbia and Chicago are very similar colleges. The only advantage I see with Columbia is if you’re interested in Engineering.
Does the faculty tuition benefit pay more if you attend UChicago? Or does it cover Columbia tuition at the same rate?
I’ve heard that the ED1 and ED2 acceptance rates at Chicago are similar. Your chances are obviously highest if you apply ED1 Chicago. But based on the points above, I think option #2 makes good sense.