I went there for new year. Saw fireworks at the navy pier.
You absolutely, must! have to go! to the "Galloping Ghost" arcade. It's not downtown, but pretty close. You're not going to be walking there.
Be prepared to spend $20.00 every time you park, or learn to use the subway.
I went to a nice breakfast place, really close to wrigley field, and a Ohio State bar. It was called something like PB&J or something similar. Just a little brekafast place in a corner, jam packed with people, but really good. Not fancy, but great breakfast food.
A lot of people will recommend Gino's, I wasn't a fan. It was good, but tasted too much like pie crust. I didn't feel I wasted my money, but have no desire to go again.
I will probably catch a shit storm, cause it's a chain. But if you go to the navy pier, there is a restaurant called bubba gump shrimp. We don't have them in ohio, and I was first introduced to it in Gatlinburg TN. I love Bubba Gump Shrimp. They have amazing jambalya, and this kick ass appetizer called spicy cajun shrimp. Basically it's a pool of butter infused with hot spices, and the shrimp is cooked in it. It comes with french bread, to dip in the butter. It's one of my all time favorite things. That french bread in the butter is killer. They actually don't have that on the menu in the Chicago Navy Pier one, but if you ask they will make it.
A lot of people recommend the Bean as well. It's OK, more of a 5 minute visit to take a picture. It's a giant bean shaped mirror thing you can walk under.