Chicago did not earn its nickname "The Windy City" because of all the sweet-talking politicians. No, this awesome place also has some infamous history with weather.
The wind is notorious, and the winter is definitely something to write home about. Bring warm clothes, blankets, and hot chocolate, because after the last part of November, Chicago will be cold and windy until May. Any Chicagoan would boast, though, that a "Chicago Summer" is worth any hard winter.