It sounds as though you've now had the Complete Train Tour of the greater Chicago area. :) Yikes, what a long journey! I give you a lot of credit for even attempting to do this. It's unfortunate that the train schedules aren't more coordinated. That happens here sometimes too, and it's always a pain. Sitting in a train station somewhere when you're tired and you just want to go home isn't fun.

As a compromise, if you don't want to drive the whole way but the public transport is such a hassle, would there be a way to drive part of the way and cut *one* of the trains out? For instance if Doris picked you up and dropped you off directly @ Union Station or if you drove to another station where you could intercept that second train? Admittedly it still means you'll be driving a little, but not as much.