Stop at some hotel an hour away, and have a good rest.
Go through on a Sunday morning.
I try to do that with Atlanta (I've had a near accident every single time).
Or bypass and take 290/53/355 due south to 80, then head east to Gary and the 31.
It's two sides of a small triangle, but they won't get stuck in downtown Chitown.
It looks like there is an Amtrack direct to GRapids but they'd have to go north or to Milwaukee to a station.
https://www.amtrak.com/stations/grr
Pets might be a problem unless there are rolling cages. Not very comfortable and maybe a layover.