Tips For How to Survive a Chicago Winter A Mild Chicago Winter + What's Been Going On Over Here 21 Things to do in Chicago in the Winter (And What to Wear!) Kristina does the Internets: How to Dress for a Chicago Winter Chicago Winter Packing List I think I'm getting the hang of this cold weather dressing thing! Here's what I'd pack for a visit to Chicago in the wintertime. This works for Chicago Dress Celestial Navy Winter Water Factory