Come on...My boats only hit the water once so far this year! Don't make me think of that chore just yet. Actually late October is plenty early. One time I had to shovel snow off the boat when I left it in the harbor until mid-November. The all day run through the Chicago river (it was a sailboat and you have to wait for them to raise the bridges, maybe 10 bridges total) left me shivering for a week. And usually I don't mind the cold!
Where in Illinois? It makes a big difference. The weather in Cairo is way different than in Chicago, especially in those "transitional" months in the fall.
if the weather is going to get much below freezing for more than a day you need to get it done. sooner than that really. I live over in Missouri and usually I am done boating by the middle of October.
when it wants to in the fall