The Cubs are out of it but still catch a game. Wrigley Field and the area around it is always cool before and after a game. You can hit up a place called Uncommon Ground for a bite to eat and beer, it's right on Clark. It's a good casual place that uses organic ingredients from local markets in their food, a good selection of beers and a cool staff.
The new Sears Tower skydeck is touristy but it's worth a visit. Basically a 100% glass box that sticks out 4 feet from the side of tallest building so you can look straight down. It feels pretty weird.
So many good restaurants I can't even start to list them and you don't need to spend a lot of money to eat good. There is a local show here on PBS called Check Please that has regular people review restaurants. Their site is a cool place to pick out a few spots you may want to try...
http://www.wttw.com/main.taf?p=1,5