If you are are appreciative of fine dining, and love watching cooking shows get a reso at El Ideas. It is still #1 on my wife and my list of food experiences ever. It is open kitchen and between courses you mingle with the other patrons and watch you food be prepared. The dishes are served and explained by the head chef. Just incredible.
I did the Chicgo Pizza Tour and it was really good.
https://www.yelp.ca/biz/chicago-pizza-tours-chicago
Korean Mexican is so good, loved this place for lunch:
https://www.yelp.ca/biz/del-seoul-chicago
Use HotWire for a hotel, we got a smoking deal ($150/night) on a 4 star that ended up being the Sofitel.