I've got 2 days to fill on my own when travelling with work and hoped someone would have some great suggestions on where I want to visit. is it worth hiring a car to see anything nearby. I love small quirky towns etc
If you like independent shop/bars go to Wicker Park for a wander. Take a river trio through the city. Have a cocktail at the top of the Hancock building. Eat a massive pizza at Pizza UNO. Shop on the Magnificent Mile. Catch a baseball game at Wrigley Field. Loads to do without leaving the city.