Exactly what bakerstreet said. Growing up we always went to the Sears Tower. It wasn't until I was an adult that I visited the Hancock and boy was that a treat! Hancock has breathtaking views during the day and stunning ones at night. My hubby and I had a date night last month that ended with tea at the Signature Room lounge. It was a gorgeous night.

Also, you might consider Art Smith's Table Fifty-Two. The food is delicious! Very cozy place with excellent service. Have a great time in Chicago and a wonderful visit with your son.