Best shoes
9 best shoes for Chicago in August
highs of 82°F, lows of 65°F, 9 rainy days — here's what to put on your feet.
Why these shoes for Chicago in August
Chicago in August averages highs around 82°F, lows near 65°F, 9 rainy days.
Chicago wind and long lakefront walks demand stable soles; winters need real insulation. Expect long walking days in Chicago: flat pavement is kind to most walking shoes.
Plan on two pairs — one built for the weather extremes and a lighter backup for evenings and dry stretches.
Our picks focus on everyday sneakers, walking shoes, slip-ons — enough range to cover day-to-day walking without overpacking.
How many pairs?
Pack two pairs
Recommendation: 2 pairs
- Primary: waterproof or water-resistant pair for wet sidewalks.
- Backup: drier/lighter pair for dinners and transit.
Best everyday sneakers for Chicago in August
ForecastStyle pick
White tennis court sneakers
Low-profile court sneakers in white with a non-marking rubber sole. Works on the tennis or pickleball court and styled with a matching set.
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ForecastStyle pick
Black chunky sneakers
Platform lug-sole sneakers in black. Adds height and works with straight-leg jeans, midi skirts, or wide-leg trousers.
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Stone
Stone Urban Traction Low Sneakers
Stone-colored low sneakers with urban traction for wet marble and brick. Clean upper keeps them looking everyday, not outdoor-specialty.
Shop on Amazon →Best walking shoes for Chicago in August
ForecastStyle pick
Classic White Low-Top Everyday Sneakers
Crisp white low-top sneakers with a clean court silhouette for everyday travel. Easy to style with jeans, skirts, or joggers and light en…
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ForecastStyle pick
Cozy Knit Slip-On Sneakers in Black
A sock-like knit upper hugs your foot for all-day comfort. The cushioned sole makes them perfect for weekend errands or travel days.
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Sand
Sand Beige Lightweight Walking Sneakers
Neutral sand-beige walking sneakers that hide dust on long sightseeing days. Breathable upper and cushioned midsole for mild-to-warm dest…
Shop on Amazon →Best slip-on shoes for Chicago in August
ForecastStyle pick
Brown leather loafers
Slip-on loafers in tan leather with a penny detail. Goes with trousers, straight-leg jeans, or a pleated skirt.
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Charcoal
Charcoal Ultralight Waterproof Slip-On Sneakers
Charcoal ultralight waterproof slip-ons for security lines and sudden storms. Packs nearly flat—ideal as a dedicated rain pair beside dry…
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ForecastStyle pick
Black Low Block-Heel Slingback Flats
Black slingback flats with a low block heel for dinners and theater nights. Secure strap and flexible sole keep them practical for short …
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FAQ
Are waterproof shoes necessary in Chicago in August?
Probably worth it — about 9 rainy days on average. Water-resistant will do; full waterproof is overkill.
Do I need boots in Chicago in August?
Not really — average lows near 65°F stay above the boot threshold. A supportive sneaker is enough.
Can I wear sandals in Chicago in August?
Absolutely — with highs around 82°F, sandals are the daily driver.
Can I get by with one pair of shoes in Chicago in August?
Many travelers do fine with one strong walking pair. Add a second only if you need dress shoes or a wet-weather dedicated option.
What about dressy dinners in Chicago?
Most cities accept clean sneakers or light boots for smart-casual dinners. If you have a black-tie night, pack one dress shoe and wear your walking pair on the plane.
Any tips for packing shoes for Chicago?
Wear the bulkiest pair on the plane, stuff socks into the packed pair, and use a shoe bag so damp soles do not ruin clothes. Pack a thin spare pair of socks for rainy days.