get out of the loop (after you see a few things). not that the loop is completely lacking, if you have never been to chicago millenium park is fun to walk through and the art institute is nice, but after around 8-9pm the loop basically shuts down.

it's not the best pizza, people have already suggested places for that, but if you want the biggest slice of pizza you've ever had go to bacci pizzeria (it's super good when you're drunk, partly because it's pizza, partly because it is so huge). take the red line north and get off at addison, it's right outside of the stairs of the stop. you'll just happen to be next to wrigley field too.

someone already said it, but the galleries in the west loop are nice (and free). the museum of contemporary art is good too, and kind of close to you (walk up michigan and take a right on chicago, 220 E Chicago Ave).