Chicago is a special place to me. The first time I ever purchased my own plane ticket, it was for a trip to the Windy City to visit my bestie who went to the University of Chicago. (Smarty pants.) When I started my stint in the travel industry five years ago, I took advantage of my stand-by airline benefits to visit her often. She has since moved to London, but now work brings me back a couple of times a year, and it's always a treat!