Best shoes
8 best shoes for Chicago in June
highs of 80°F, lows of 61°F, 10 rainy days — here's what to put on your feet.
Why these shoes for Chicago in June
Chicago in June averages highs around 80°F, lows near 61°F, 10 rainy days.
This is a versatile shoe month — one comfortable everyday pair covers most days, with a lighter or heavier option in reserve for the outliers.
Our picks focus on everyday sneakers, walking shoes, slip-ons — enough range to cover the day-to-day walking without overpacking.
Everyday sneakers
Allbirds
Tree Runners
Lightweight, machine-washable, dries fast after an unexpected shower.
Buy on Amazon →Walking shoes
Hoka
Clifton 9 (Men)
Cushion for 20k+ step days; the shoe your feet will thank you for.
Buy on Amazon →Slip-ons
FAQ
Are waterproof shoes necessary in Chicago in June?
Yes — with roughly 10 rainy days in the month, waterproof or water-resistant shoes are a strong bet.
Do I need boots in Chicago in June?
Not really — average lows near 61°F stay above the boot threshold. A supportive sneaker is enough.
Can I wear sandals in Chicago in June?
Absolutely — with highs around 80°F, sandals are the daily driver.