Ken: Ironically, I lived in Illinois from 2nd grade through high school and I love the Chicago area. If we go to Alabama after the CICO we'll definitely go through Illinois and Kentucky. If not this year, then next. Living in the PNW makes it tough; you have to drive a LOT of miles to get to the midwest.
Anna & Steve: I think Florida will warrant its own trip! On our way back from Alaska, I think we'll come back into the states via North Dakota, sneak down to South Dakota and then stop in Minnesota before we go on to Michigan then backtrack to Necedah. Seems a little like cheating, though.