I have been lucky flying long distances in the winter, but as you have said, flexibility is required for GA. I think the odds of making your flight without dealing with icing conditions on your 5 hour (non-stop?) flight will require some luck. If not clear, just snow could work VFR. Will the timing between fronts line up with a next day flight from PWK to keep you in the daylight and avoiding IMC icing, or will you need to delay your departure 1 or more days to get back home. Do you feel lucky? While I would want to do this flight, winter conditions are always more troublesome. How are you doing your preheat at PWK. Oh, you are putting it in the hangar overnight(s). This will not be an inexpensive pickup, although I do like adventure.
The reliability of picking her up from a closer airport from a drive, or GA flight, can not be overstated.