The Windy City is an eclectic mix of modern art, buzzworthy dining, cutting-edge comedy, and beloved sports teams. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theatre companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh to the point of tears at the Second City Theatre, the launch pad of many famous comedians.