Aside from the pride parade, our time in Chicago was done by the book. My mom is from a suburb so I've been to the city quite a few times. I was able to play tour guide for Karin, hitting all the must-see spots in basically one day.
Karin was really impressed by the architecture. She and I have been to cities that are much bigger by land area or population, but Chicago has some serious sky scraper action that's impressive even for a repeat visitor like me.