A first weekend in Chicago
Art Institute of Chicago: choose your gallery visit
Lincoln Park: Nature Boardwalk and a free zoo visitAn example packing list for Chicago in May
Use this as a starting point and choose what suits your plans. Packtricia tailors your list and quantities to your trip length, weather and preferences.
Clothing
- Underwear
- Bras (if worn)
- Socks
- Sleepwear
- Long-sleeved shirt or breathable top
- Comfortable trousers
- Removable knit
- Packable windproof rain jacket
- Broken-in walking shoes with grip
Toiletries
- Toothbrush
- Toothpaste
- Shampoo
- Conditioner
- Body wash or soap
- Deodorant
- Skincare products
- Sunscreen
- Hairbrush or comb
- Shaving supplies (if used)
- Menstrual products (if needed)
- Contact lens solution (if used)
Essentials
- Passport or accepted travel ID
- Travel tickets and booking confirmations
- Wallet and payment cards
- Phone
- Charging cable and charger
- Travel adapter (if needed)
- Medication (if needed)
- Glasses or contact lenses (if used)
- Refillable water bottle
- Day bag
- Power bank (if needed)
- Water-resistant pouch
- Compact umbrella (if preferred)
Monthly weather and packing notes
May often allows a lighter daytime top, but carry a knit and windproof rain layer for a boat deck. Closed walking shoes fit the Nature Boardwalk and museum route, with sun protection and water useful when you spend longer outside between indoor stops.
- Daytime
- 19–23°C
- Evenings
- 8–12°C
- Rain
- Showers possible
- Daylight
- Check sunset when planning the park or a waterfront finish.
- Packing style
- Removable layers and comfortable closed shoes
National Weather Service Chicago O’Hare station normals cover 1991–2020. Mean daily maximum 70.5°F (21.4°C), minimum 50.6°F (10.3°C), monthly precipitation 4.49 inches (114.0 mm). Clothing bands convert to Celsius, round and expand by 2°C each way; these are outfit prompts, not forecast limits. Precipitation includes water-equivalent snow. Airport exposure differs from downtown streets, riverbanks and the lakefront. Check the forecast for your actual travel dates.
Outfit ideas for your outings
May around Millennium Park
- Long-sleeved shirt or breathable top
- Removable knit
- Comfortable long trousers
- Walking footwear with grip
- Packable windproof rain jacket
A Riverwalk or open boat-deck outing
- Long-sleeved shirt or breathable top
- Removable knit
- Packable windproof rain jacket
- Sun protection
- Secure comfortable footwear
Art Institute galleries and an indoor stop
- Long-sleeved shirt or breathable top
- Removable knit
- Comfortable trousers or skirt
- Closed shoes
- Day bag to store outer layers
What to leave behind
- Stiff unworn shoes: test footwear before Loop paving, park paths and transit stairs.
- Only a summer outfit: a rain shower, indoor air conditioning or waterfront wind can still need an extra layer.
Reviewed 2026-10-13
National Weather Service: Chicago O’Hare 1991–2020 normals · Choose Chicago: first-time visitor routes · CTA: route, payment and access guidance