I'm only concerned about Leslie's replacementfor all the understudies. To the op: would it make sense for you to stand in cancelation for non premium tickets or hire a line sitter? That would be cheaper. I think one of your biggest costs will be hotels and trandportation. If If I were you I would take a plane or train, whichever is cheaper (I don't live in Chicago) that arrives at around 12-3 at night and wait in cancelation for tickets, rejecting premium tickets as to cut back on cost. You can refuse premium and not loose your place in line. 2 is an optimal amount for waiting in line. You two can swap out and keep your place in line, going to get food while the other waits. The Richard Rodgers is right near times square so there are plenty of options and it's not like you're gonna get murdered at that time of night (it's not the meatpacking district.) See the show, (assuming you get tickets. I have not heard stories of anyone first in line not getting tickets through cancelation, so it seems to be a pretty sure bet but don't quote me), stage door and take transportation back to Chicago. This whole thing would be to eliminate the costs of hotels, line sitters and resale tickets. Whenever and however you see the show, I hope you love it. Sorry if you knew all this, and by the way, it may be wise to attend a matinee if you are using this plan.
I appoligise for any spelling mistakes. I may be on my mobile. Clumsy fingers and small little touchscreen keys don't mixx. I try to spellcheck, but I may miss something.