Wouldn't it be easier to Start at the Dunes Club, in New Buffalo, MI (gotta be a magical place), pick something logistically by an airport across the time zone or Chicago which is very nearby. Play there, fly to Boise ID and play Hillcrest, drive to Ontario, OR and play. Unless of course Ontario is still in Mountain time. I don't remember for sure.
EDIT. Ontario is Mountain time. This is harder than I thought to find a one flight option.
How about fly to Missoula, MT, play there. Drive just across the border in ID and play Shoshone Country Club, or Kellog Country Club.
Commercial flight here is 12:06 p.m. to 4:19 p.m. Shows a direct flight would be necessary to get it done.
EDIT again: I thought I might have found a way to do it by commercial flight. Fly to SLC, play, drive to West Wendover, NV and play Toana Vista Golf Course. Unfortunately they keep screwing with the time zones and moving them off the borders, so West Wendover is in mountain time. Same thing that caught me up flying to Boise.