I just wanted to give a quick update:

Due to the snow, we ended up canceling some of our plans and only going to the concert on Friday at Martyrs'; one of the two artists was coming from Michigan and he canceled due to weather. In the end, that meant the singer I preferred played longer and it was a great show. We decided just to eat at Martyrs' (and it was pretty good)!

Saturday we went to the Oriental Institute, which was new to both of us and tried Gino's Pizza, which was recommended by a friend. We also went to Shedd.

Wicked was great and our seats were perfect; we parked in a garage a few blocks away and had no trouble (thankfully) with parking. We actually found free parking across from both Martyrs' and the Oriental Institute so we were very lucky in that respect.

Thank you to everyone for all the suggestions in the thread; we're already planning our next trip back!