Howdy!
As previously mentioned I reserved my tickets with the 4 hours of hanging out in Chicago eating deep dish pizza. The train arrived in Chicago about 15 minutes late, with 15 minutes to get on a train bound for Milwaukee.
I'm thinking, "welp, maybe I'll saunter over to the ticket window and see if they'll let me get on the Milwaukee train leaving in 15 minutes......"
They did. So I did. And got into Milwaukee earlier than planned. I'm going to post a bit more of a trip report in the Great Lakes Regional folders, as I posted questions about Wisconsin and Door County there, and got some nice pointers and help.
Thanks for everyone's comments.
Happy Trails.