Pack or skip
Hiking boots for Chicago in September
Verdict
Optional
Hiking boots depend on your itinerary, not the weather — pack them if you're on trails.
Why
Chicago in September averages highs of 74°F, lows of 57°F, 9 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.