Chicago, Illinois
Chicago winters are exceedingly brutal. Expect mountains of snow and wind-chills so low it could make a grown man cry. Winter seems to last so long in Chicago, it almost feels like nothing ever existed outside of it. Before residents of the Illinois metropolis lock themselves indoors away from the cold and vow to never leave their apartments unless it’s an emergency, there actually is autumn. And autumn is really quite nice. The crisp breeze, the changing leaves and the variety of open parks make it a particularly lovely time to wander around the city. Just make sure you bring a scarf and a hat (and probably an extra warm pumpkin spice latte or two).
