Pack or skip
Hiking boots for Chicago in November
Verdict
Optional
Hiking boots depend on your itinerary, not the weather — pack them if you're on trails.
Why
Chicago in November averages highs of 48°F, lows of 35°F, 10 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.