One item I always pack for Chicago weather is a hairbrush. One minute you can be walking down the street and as soon as you turn the corner, you feel like you are walking through a wind tunnel. Chicago did not receive the nickname "The Windy City" for no reason. It is essential to have because the wind can come out of nowhere and mess up the time you spent on your hair to look presentable. Whether you are walking into work, to lunch, to meet a client, or simply for leisure, the wind can quickly change up your look!