Going to Chicago to see a great play, have dinner and see some of the city is part of my favorite things to do.  The plays are in some of the most charming theaters, not large, just perfect for good seating regardless of what tickets you get.  You can see and hear and thoroughly enjoy.

The choice of restaurants is endless in the city.  There is one that just tickles me, it's the Italian Village which has 3 choices in one location.  The food is good and the prices reasonable.  The environment is supposed to be that from Italy, not sure if it is, but it's fun anyway.

We usually get a hotel on Priceline, it saves us some money and we have stayed in some really neat places.  Boutique hotels, the Hilton, The Palms and others. 

We have been to New York to a play too, it was great, but don't honestly think it would be that much better than in Chicago and Chicago is a lot cheaper!  We can drive, the tickets are less and the hotels are less expensive.  If you haven't been to Chicago to a play, try it, you may like it.