I'm visiting ye olde Windy City for the first time next month. My mom is going for a conference for 3 days and wants company. She is a pretty miserable traveler/travel partner but she has been going through a rough bit with my Nana and I have some friends that live there so why not? What should I do? Both touristy and Chicago insider tips appreciated!

ETA: Thank you for the tips so far! I'm adding them to my google doc!