Steely skyscrapers, top chefs, and rocking festivals – the Windy City will blow you away with its low-key cultured awesomeness. Chicago knows how to rock a festival. Between March and September, it throws around 200 shindigs. The specialty is music. Blues Fest brings half a million people to Grant Park to hear guitar notes slide and bass lines roll, all for free. Chicago really is my kind of town.