Pack or skip
Flip-flops for Chicago in January
Verdict
Skip it
Highs around 32°F — too cool for open shoes.
Why
Chicago in January averages highs of 32°F, lows of 17°F, 11 rainy days.
That climate means flip-flops isn't pulling its weight. Highs around 32°F — too cool for open shoes.
What to bring instead
See our best-shoes picks for Chicago in January →