Chicago has bean on my travel list for a while now (lol, see what I did there). Sadly, a professional conference is not the best way to see a new city, since you spend all day, every day, in panel sessions and net working events. So, for my first four days in Chicago, I basically saw the Palmer hotel and surrounding block.
Fortunately, my friend Sophia was also presenting at the conference and we decided to book an extra day and a half to explore the city. While a day and a half is not nearly enough time for a city like Chicago, we managed to pack in most of the major highlights.
Per usual, starting early is the key to maximizing your time. We opted for the early bird entrance to the famous Sears/Willis tower. And it was completely worth it. Not only did we not have to wait in a line, we had the entire sky deck to ourselves before it opened to the public! We made the most of it and had too much fun taking ridiculous pictures. If you don't know what the sky deck is, it is a collection of four clear glass boxes that hang off the side of the western hemisphere's tallest building (well, tallest until 2014 when One World Trade Center was completed). Let me tell you, these boxes make for some crazy views! They say on a clear day you can see four states. But, don't worry, it is not as scary as you think.
In addition to the Sky Deck, we visited the famous Bean sculpture in Millennium Park, the Chicago Art Institute, brunched at The Hampton Social, went on an architectural river tour, strolled the Magnificent Mile, and had dinner at the famed Siena Tavern (although as part-time Florentines, we were not supper impressed with their take on Tuscan cuisine). On my extra half day, I was able to meet up with a friend and fellow Italian scholar and explore Wicker Park and grab the famed Negroni slush at Parson's.
Overall, I think it was a nice highlight tour of Chicago, although I would love to return and see more!