Normally I would side with your mother, but since he’s from the same place as you, then he will be headed in your direction with some regularity to see family, as his finances and schedule dictates. You were friends in the past, so that makes things a little different than a complete stranger. Grad school is going to lock him into place for long time, so if a relationship is to come of this, you will have to be the one to compromise. If you can get cheaper airfare to Chicago, would he be willing to pick you up there? It’s about 2–1/2 hours from Bloomington. I’m assuming he’s at IU-Bloomington? It’s a really fun little college town. I say go. Then you’ll have a better idea about what you want to do. Don’t overstay; 3 days should help you figure it out.