I don’t have a recent South Shore Line schedule at hand...but Gary should be less than an hour’s direct ride from Chicago, objectively speaking. I suspect many of the “Gary” riders actually live in nearby Merrillville and Schererville (which exploded as people escaped Gary’s collapse in the early 1970s) and drive to a nearby stop like Hammond or Miller, both of which straddle Gary.
My sons wife’s family lived in downtown Chicago close to the Trump building. They sold out and moved to Florida three years ago, they have no regrets.