Best shoes
9 best shoes for Chicago in November
highs of 48°F, lows of 35°F, 10 rainy days — here's what to put on your feet.
Why these shoes for Chicago in November
Chicago in November averages highs around 48°F, lows near 35°F, 10 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 November
ForecastStyle pick
Grey slip-on sneakers
Slip-on canvas sneakers in heathered grey. An easy everyday shoe — good with joggers, jeans, or a casual dress.
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Retro
Retro Court Chunky Sneakers in Beige
An elevated platform sole adds a modern, sporty touch to this vintage-inspired low-top sneaker. Designed for all-day comfort and versatil…
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Beige
Beige Leather Everyday Sneakers
Warm beige leather everyday sneakers that hide dust better than pure white. Flexible sole for sightseeing and a polished finish for casua…
Shop on Amazon →Best walking shoes for Chicago in November
ForecastStyle pick
The Everyday Cloud Sneaker in White
A flexible knit upper and cushioned insole provide all-day comfort for travel days, commutes, or weekend errands. Pairs effortlessly with…
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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…
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ForecastStyle pick
Grey Road-Ready Walking Sneakers
Cool grey road-ready walkers with balanced cushion—not chunky trail, not dress flat. Designed for flat pavement, metro stairs, and long a…
Shop on Amazon →Best slip-on shoes for Chicago in November
Evergreen
Evergreen Shearling-Lined Suede Clogs
A molded cork footbed and plush shearling lining provide all-day comfort for errands or relaxing at home. The durable rubber sole offers …
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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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ForecastStyle pick
Black Chunky Sport Loafer Mules
These chunky-soled mules offer a sporty take on the classic loafer, with an easy slip-on design for all-day wear. The cushioned footbed a…
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FAQ
Are waterproof shoes necessary in Chicago in November?
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 November?
Yes — average lows near 35°F mean insulated boots will keep your feet from freezing on the walk back to the hotel.
Can I wear sandals in Chicago in November?
Not really — highs around 48°F are too cool for open shoes on most days.
Can I get by with one pair of shoes in Chicago in November?
Two pairs is safer — wet cold months punish a single pair. Pack a weather-ready primary and a dry backup.
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.