Best shoes
9 best shoes for Chicago in May
highs of 70°F, lows of 51°F, 11 rainy days — here's what to put on your feet.
Why these shoes for Chicago in May
Chicago in May averages highs around 70°F, lows near 51°F, 11 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, light boots, walking shoes — 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 May
ForecastStyle pick
Olive Green Everyday Low Sneakers
Muted olive low sneakers that pair with neutrals and denim. A low-profile everyday option when white feels too high-maintenance.
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ForecastStyle pick
Black low-top tennis sneakers
Sleek low-top court shoes in black with a durable outsole and padded collar. Transitions cleanly from court to street.
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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…
Shop on Amazon →Best light boots for Chicago in May
Forest
Forest green ankle boots
Ankle boots in forest green suede with a block heel. A color-forward alternative to black boots for autumn and winter.
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Dark
Dark Brown Weather-Ready Chelsea Boots
Dark brown Chelseas with a treated upper and rubber sole for light drizzle. Clean lines keep them looking city-smart, not trail-ready.
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Cognac
Cognac Shearling-Lined Ankle Boots
Cognac ankle boots with plush shearling lining for dry cold and light snow. Warm without the bulk of full winter boots—ideal for short ci…
Shop on Amazon →Best walking shoes for Chicago in May
ForecastStyle pick
Black Waterproof Knit High-Top Sneakers
Black waterproof knit high-tops that slip through security easily and dry faster than leather after a downpour. Cushioned midsoles suppor…
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ForecastStyle pick
Grey Summit Chunky Trail Sneakers
A rugged sole provides superior traction on and off the trail, while the cushioned interior ensures all-day comfort. The chunky silhouett…
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ForecastStyle pick
Black Slip-On Walking Sneakers
Black slip-on walking sneakers for security lines and early trains. Supportive footbed with a closed toe for all-day urban miles.
Shop on Amazon →Wear them with these outfits
Climate-matched looks for Chicago in May.
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FAQ
Are waterproof shoes necessary in Chicago in May?
Yes — with roughly 11 rainy days in the month, waterproof or water-resistant shoes are a strong bet.
Do I need boots in Chicago in May?
Not really — average lows near 51°F stay above the boot threshold. A supportive sneaker is enough.
Can I wear sandals in Chicago in May?
Yes, for midday. Highs around 70°F are on the edge, so plan a backup for cooler mornings and evenings.
Can I get by with one pair of shoes in Chicago in May?
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.