- Head to the Hot Tix counter for 1/2 price tickets to a show (I'm not too choosy we like live theatre in our family).
- Dinner at Wildfire - A great steakhouse. I imagine there are better in Chicago, but the whole family can enjoy this place at a reasonable price.
- Shopping along Michigan Avenue - my wife and daughter shop, and I people-watch. I also like the Apple and Niketown stores.
- A Cubs game game if they are in-town during the season - I have never been to Fenway, but it can't be better than seeing a day game at Wrigley Field on a sunny afternoon!
- At least one extended ride somewhere on the loop on the El - In my opinion, the lack of a real mass transit system is the biggest city-planning mistake Detroit has ever made.