Embrace the Layers
Don't underestimate the Chicago wind, even in May! Dressing in layers will allow you to comfortably adjust to temperature changes from morning to night, indoors to outdoors.
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Weather in Chicago in May
May in Chicago brings an average high temperature of 68°F (20°C) and an average low of 48°F (9°C), offering pleasant days but still cool evenings. While snow is highly unlikely, expect around 10-12 days of rain throughout the month, so waterproof gear is a must. Humidity levels are generally moderate, making for comfortable conditions, and you'll enjoy long daylight hours with the sun setting around 8 PM by late May.
What to wear in Chicago in May
Layering is your best friend in Chicago during May. Think versatile pieces you can easily add or remove as temperatures fluctuate throughout the day. Locals generally dress in smart casual attire, so you'll fit in with anything from jeans and a stylish top to slacks and a light blazer, especially when dining out or visiting cultural attractions.
Essentials for Chicago in May
Waterproof Packable Jacket
A lightweight, waterproof jacket is essential for unexpected May showers and provides an extra layer against the occasional brisk winds.
Comfortable Walking Shoes
You'll be doing a lot of walking exploring Chicago's magnificent architecture and expansive parks, so supportive, broken-in shoes are a must.
Lightweight Scarf
A scarf is perfect for adding warmth on cooler evenings or protecting against unexpected drafts, and can also elevate a simple outfit.
Portable Umbrella
Compact and easy to carry, a small umbrella will be invaluable for sudden rain showers that are common in spring.
Power Bank/Portable Charger
Keep your phone charged for navigation, photos, and Ubers as you explore Chicago's many attractions throughout the day.
Small Crossbody Bag
Ideal for keeping your essentials secure and easily accessible while navigating crowded attractions or public transport.
Long-Sleeve Layers
Pack a mix of long-sleeve t-shirts or light sweaters for those cooler mornings and evenings.
Beanie or Light Hat
Especially useful for boat tours or walks along the lakefront where the wind can be surprisingly chilly.
Sunglasses
Even on cooler days, the sun can be bright, especially when reflecting off the lake or city skyscrapers.
Reusable Water Bottle
Stay hydrated while exploring the city; many places have water fountains or willing staff who can refill it for you.
Pro tips
Waterfront Wind Chill
If you plan on taking an architectural boat tour, visiting Navy Pier, or walking along the lakefront, be prepared for significantly cooler temperatures and stronger winds than downtown.
Check the Forecast Daily
Chicago weather can be famously fickle. Check the local forecast each morning to fine-tune your outfit choice for the specific day ahead.
Pack for Versatility
Choose clothing items that can be mixed and matched to create multiple outfits, helping you pack lighter and be prepared for various occasions from casual sightseeing to a nicer dinner.
Public Transportation Smart
Chicago has an excellent public transportation system. Factor in walking to and from transit stops when considering shoe comfort and outer layers.
Frequently asked
What kind of jacket should I bring for Chicago in May?
A waterproof, packable jacket is your best bet. It will protect you from rain and provide a good barrier against the wind, which can still be brisk in May. You won't likely need a heavy winter coat, but something substantial enough for 40-50°F evenings.
Is it still very windy in Chicago in May?
Yes, while not as fiercely cold as winter, Chicago lives up to its 'Windy City' nickname year-round. Expect breezy conditions, especially near the lakefront and between tall buildings. A light scarf or hat can be surprisingly helpful.
What shoes are best for exploring Chicago in May?
Comfortable, closed-toe walking shoes are paramount. You'll be on your feet a lot! Consider waterproof options as rain showers are common. Save the open-toed sandals for warmer, more predictable weather.
Should I pack formal wear for Chicago in May?
Unless you have specific plans for a very upscale event or restaurant, smart casual attire is generally sufficient. A nice pair of shoes, dark jeans or slacks, and a stylish top or light blazer will get you into most places comfortably.
Is an umbrella necessary in May?
Absolutely! May typically sees about 10-12 days of rain in Chicago. A compact, portable umbrella will be a lifesaver for unexpected spring showers and will keep you dry while exploring the city.
Will it be warm enough to eat outdoors?
Many restaurants begin opening their patios and outdoor seating in May. While days can be warm enough, evenings can still be cool, so be prepared with an extra layer if you plan on dining al fresco after sunset.