Pack or skip
Flip-flops for Chicago in December
Verdict
Skip it
Highs around 36°F — too cool for open shoes.
Why
Chicago in December averages highs of 36°F, lows of 22°F, 11 rainy days.
That climate means flip-flops isn't pulling its weight. Highs around 36°F — too cool for open shoes.
What to bring instead
See our best-shoes picks for Chicago in December →