Pack or skip
Hiking boots for Chicago in December
Verdict
Optional
Hiking boots depend on your itinerary, not the weather — pack them if you're on trails.
Why
Chicago in December averages highs of 36°F, lows of 22°F, 11 rainy days.
That climate makes hiking boots a judgment call. Hiking boots depend on your itinerary, not the weather — pack them if you're on trails.