Pack or skip
Flip-flops for Chicago in October
Verdict
Skip it
Highs around 62°F — too cool for open shoes.
Why
Chicago in October averages highs of 62°F, lows of 46°F, 9 rainy days.
That climate means flip-flops isn't pulling its weight. Highs around 62°F — too cool for open shoes.
What to bring instead
See our best-shoes picks for Chicago in October →