What's your interests??and what dates??Check out the local bars buddy guy ledgends is cool if your a blues fan.House of blues is local in the towers,chicago has CRAZY architecture so thats cool just to take the riverboat tour~ and food? it's the midwest so we don't eat ANYTHING health it's all full fat and fun!if your the Pizza fan check lou malnati's or pizzeria uno ~bbq ~gale street in best ribs around may be a cab ride for ya' depending where your staying,hi class dining you can TRY to get in to the trump towers and they have a very nice place I think it's good VERY pricey ,cuz' we all know trumps living check to check!For free stuff check out the "bean" and buckingham fountain,theres tons of museums in the area a planitarium and navy pier is a good chill out place sit an the end watch live bands and drink beer and eat next to the lake it's just about damn near perfect,except i don't drink! I don't know your dates but the burbs are great 20 minute cabrides to great fun,lots of good small bars and music,let me know your dates and i can shoot ya' some attractions that week!