On paper, the electric train from Chicago will will lure you in. Resist. It is a long, slow ride ...
I took the South Shore from SB to Chi a few times in my years at ND. It was affectionately (?) known as the Vomit Comet in my day. Always an adventure. My first time on the SS was my freshman year for Christmas break. It was the only time in four years that I flew from O'Hare to Orlando (and vice-versa) for a break, be it Christmas, Spring or Summer.
On my return flight from Orlando I was flying with a high school classmate, his older brother and a cousin – all Domers. The flight went fine. Getting to the SS station went fine. Getting from Chi Town to SB ... not so good. The engine on our train broke down. They announced (no lie/true story) that there would be an hour delay while waiting for the next train to come and push us.
Well, I had a grocery bag of oranges and a grocery bag of grapefruit I'd had as carry-on. I also had bottles of Scotch, Rum, Gin and Vodka I'd "procured" from a political gathering I'd helped with (parking cars and cleaning up afterwards) in my suitcase. It didn't take long for me to declare that it was Happy Hour. "Screwdrivers for the car!"
One woman who was bringing groceries back to SB after her day at work volunteered salami as an appetizer. Another offered a cake for dessert. We thought we were busted when a porter entered the car. He didn't ask for ID or order us to cease and desist, he simply asked "when am I going to get a drink?"
It was a long trip, but I was a pretty happy traveler when we hit the station in South Bend.