My parents are both from the Chicago area, so I have had a chance to visit several times throughout my life. As a kid, I enjoyed Navy Pier a lot. I have four sisters, so when my mom and my sisters went shopping, my dad and I would go to the Nike store as I have always lived sports. When I was a lot younger, the Lego store was awesome, but I can remember the prices were absurdly high. Another idea is the top floor of the John Hancock building. Depending on the weather, the view is tremendous. As far as dining goes, my dad and I would usually meet my sisters and my mom at Gran Lux Cafe after a day of sightseeing/shopping. I can't remember where we would go for dinner, but there are literally hundreds of spots to choose from. There aren't too many places you can go wrong. Hope this helps. PM me if you have any questions or if you want the specifics of any locations or the like--I can ask my dad about them.